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<span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hardness" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hardness"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Hardness</span> </div> </a> <ul id="toc-Hardness-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Spectroscopy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Spectroscopy"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Spectroscopy</span> </div> </a> <ul id="toc-Spectroscopy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Optical_activity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Optical_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Optical activity</span> </div> </a> <ul id="toc-Optical_activity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Nomenclature</span> </div> </a> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Chemical properties</span> </div> </a> <button aria-controls="toc-Chemical_properties-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Chemical properties subsection</span> </button> <ul id="toc-Chemical_properties-sublist" class="vector-toc-list"> <li id="toc-Adamantane_cations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Adamantane_cations"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Adamantane cations</span> </div> </a> <ul id="toc-Adamantane_cations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Bromination" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Bromination"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.1</span> <span>Bromination</span> </div> </a> <ul id="toc-Bromination-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fluorination" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Fluorination"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.2</span> <span>Fluorination</span> </div> </a> <ul id="toc-Fluorination-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carboxylation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Carboxylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.3</span> <span>Carboxylation</span> </div> </a> <ul id="toc-Carboxylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.4</span> <span>Oxidation</span> </div> </a> <ul id="toc-Oxidation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Others" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Others"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.5</span> <span>Others</span> </div> </a> <ul id="toc-Others-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-In_medicine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_medicine"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>In medicine</span> </div> </a> <ul id="toc-In_medicine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_designer_drugs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_designer_drugs"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>In designer drugs</span> </div> </a> <ul id="toc-In_designer_drugs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Spacecraft_propellant" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Spacecraft_propellant"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Spacecraft propellant</span> </div> </a> <ul id="toc-Spacecraft_propellant-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Potential_technological_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Potential_technological_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Potential technological applications</span> </div> </a> <ul id="toc-Potential_technological_applications-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Adamantane_analogues" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Adamantane_analogues"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Adamantane analogues</span> </div> </a> <ul id="toc-Adamantane_analogues-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" 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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Adamantane</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 28 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-28" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">28 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%AF%D8%A7%D9%85%D8%A7%D9%86%D8%AA%D8%A7%D9%86" title="أدامانتان – Arabic" lang="ar" hreflang="ar" data-title="أدامانتان" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%AF%D9%85%D9%86%D8%AA%DB%8C%D9%86" title="ادمنتین – South Azerbaijani" lang="azb" hreflang="azb" data-title="ادمنتین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%B4%D0%B0%D0%BC%D0%B0%D0%BD%D1%82%D0%B0%D0%BD" title="Адамантан – Belarusian" lang="be" hreflang="be" data-title="Адамантан" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Adamantan" title="Adamantan – Czech" lang="cs" hreflang="cs" data-title="Adamantan" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Adamantan" title="Adamantan – German" lang="de" hreflang="de" data-title="Adamantan" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Adamantano" title="Adamantano – Spanish" lang="es" hreflang="es" data-title="Adamantano" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Adamantano" title="Adamantano – Esperanto" lang="eo" hreflang="eo" data-title="Adamantano" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D8%AF%D8%A7%D9%85%D8%A7%D9%86%D8%AA%D8%A7%D9%86" title="آدامانتان – Persian" lang="fa" hreflang="fa" data-title="آدامانتان" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Adamantane" title="Adamantane – French" lang="fr" hreflang="fr" data-title="Adamantane" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Adamantana" title="Adamantana – Indonesian" lang="id" hreflang="id" data-title="Adamantana" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Adamantano" title="Adamantano – Italian" lang="it" hreflang="it" data-title="Adamantano" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%B4%D0%B0%D0%BC%D0%B0%D0%BD%D1%82%D0%B0%D0%BD_(%D1%82%D1%80%D0%B8%D1%86%D0%B8%D0%BA%D0%BB%D0%BE%D0%B4%D0%B5%D0%BA%D0%B0%D0%BD)" title="Адамантан (трициклодекан) – Kazakh" lang="kk" hreflang="kk" data-title="Адамантан (трициклодекан)" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Adamant%C4%81ns" title="Adamantāns – Latvian" lang="lv" hreflang="lv" data-title="Adamantāns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Adamantaan" title="Adamantaan – Dutch" lang="nl" hreflang="nl" data-title="Adamantaan" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%80%E3%83%9E%E3%83%B3%E3%82%BF%E3%83%B3" title="アダマンタン – Japanese" lang="ja" hreflang="ja" data-title="アダマンタン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Adamantan" title="Adamantan – Polish" lang="pl" hreflang="pl" data-title="Adamantan" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Adamantano" title="Adamantano – Portuguese" lang="pt" hreflang="pt" data-title="Adamantano" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Adamantan" title="Adamantan – Romanian" lang="ro" hreflang="ro" data-title="Adamantan" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%B4%D0%B0%D0%BC%D0%B0%D0%BD%D1%82%D0%B0%D0%BD" title="Адамантан – Russian" lang="ru" hreflang="ru" data-title="Адамантан" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Adamant%C3%A1n" title="Adamantán – Slovak" lang="sk" hreflang="sk" data-title="Adamantán" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Adamantan" title="Adamantan – Serbian" lang="sr" hreflang="sr" data-title="Adamantan" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Adamantan" title="Adamantan – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Adamantan" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Adamantan" title="Adamantan – Sundanese" lang="su" hreflang="su" data-title="Adamantan" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Adamantaani" title="Adamantaani – Finnish" lang="fi" hreflang="fi" data-title="Adamantaani" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Adamantan" title="Adamantan – Swedish" lang="sv" hreflang="sv" data-title="Adamantan" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Adamantan" title="Adamantan – Turkish" lang="tr" hreflang="tr" data-title="Adamantan" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%B4%D0%B0%D0%BC%D0%B0%D0%BD%D1%82%D0%B0%D0%BD" title="Адамантан – Ukrainian" lang="uk" hreflang="uk" data-title="Адамантан" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%87%91%E5%88%9A%E7%83%B7" title="金刚烷 – Chinese" lang="zh" hreflang="zh" data-title="金刚烷" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q351461#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Adamantane" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Adamantane" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Molecule with three connected cyclohexane rings arranged in the "armchair" configuration</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Adamantine_(disambiguation)" class="mw-redirect mw-disambig" title="Adamantine (disambiguation)">Adamantine</a> or <a href="/wiki/Amantadine" title="Amantadine">Amantadine</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Adamantane </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Adamantane_acsv.svg" class="mw-file-description"><img alt="Skeletal formula of adamantane" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Adamantane_acsv.svg/160px-Adamantane_acsv.svg.png" decoding="async" width="160" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Adamantane_acsv.svg/240px-Adamantane_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Adamantane_acsv.svg/320px-Adamantane_acsv.svg.png 2x" data-file-width="463" data-file-height="419" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantane_3D_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the adamantane molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Adamantane_3D_ball.png/120px-Adamantane_3D_ball.png" decoding="async" width="120" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Adamantane_3D_ball.png/180px-Adamantane_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Adamantane_3D_ball.png/240px-Adamantane_3D_ball.png 2x" data-file-width="1959" data-file-height="2000" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantane-3D-vdW.png" class="mw-file-description"><img alt="Space-filling model of the adamantane molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Adamantane-3D-vdW.png/120px-Adamantane-3D-vdW.png" decoding="async" width="120" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Adamantane-3D-vdW.png/180px-Adamantane-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Adamantane-3D-vdW.png/240px-Adamantane-3D-vdW.png 2x" data-file-width="1100" data-file-height="1097" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantane.JPG" class="mw-file-description"><img alt="Sample of adamantane" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Adamantane.JPG/220px-Adamantane.JPG" decoding="async" width="220" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Adamantane.JPG/330px-Adamantane.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/Adamantane.JPG/440px-Adamantane.JPG 2x" data-file-width="600" data-file-height="413" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Adamantane<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Tricyclo[3.3.1.1<sup>3,7</sup>]decane<sup id="cite_ref-r1_2-0" class="reference"><a href="#cite_note-r1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=281-23-2">281-23-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C1C3CC2CC%28CC1C2%29C3">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C1C2CC3CC1CC%28C2%29C3">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1901173 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=40519">CHEBI:40519</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1614830">ChEMBL1614830</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.8883.html">8883</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03627">DB03627</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.005.457">100.005.457</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q351461#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>206-001-4</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>26963 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/9238">9238</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/PJY633525U">PJY633525U</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5022017">DTXSID5022017</a></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ORILYTVJVMAKLC-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ORILYTVJVMAKLC-UHFFFAOYAG</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1C3CC2CC(CC1C2)C3</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1C2CC3CC1CC(C2)C3</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>10</sub><span title="Hydrogen">H</span><sub>16</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002136238000000000♠"></span>136.238</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White to off-white powder </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.07 g/cm<sup>3</sup> (25 °C)<sup id="cite_ref-r1_2-1" class="reference"><a href="#cite_note-r1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>270 °C (518 °F; 543 K)<sup id="cite_ref-r1_2-4" class="reference"><a href="#cite_note-r1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>Sublimes<sup id="cite_ref-r1_2-2" class="reference"><a href="#cite_note-r1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Poorly soluble </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in other solvents </td> <td>Soluble in hydrocarbons </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.568<sup id="cite_ref-r1_2-3" class="reference"><a href="#cite_note-r1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-bagriy_1_3-0" class="reference"><a href="#cite_note-bagriy_1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Crystal_structure" title="Crystal structure">Crystal structure</a></div> </td> <td><a href="/wiki/Cubic_crystal_system" title="Cubic crystal system">cubic</a>, <a href="/wiki/Space_group" title="Space group">space group</a> Fm3m </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Coordination_geometry" title="Coordination geometry">Coordination geometry</a></div> </td> <td>4 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>0 <a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Flammable </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H400: Very toxic to aquatic life">H400</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds:</div> </td> <td><a href="/wiki/Memantine" title="Memantine">Memantine</a><br /><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a><br /> <a href="/wiki/Amantadine" title="Amantadine">Amantadine</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477241894&page2=Adamantane">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Adamantane</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with formula C<sub>10</sub>H<sub>16</sub> or, more descriptively, (CH)<sub>4</sub>(CH<sub>2</sub>)<sub>6</sub>. Adamantane molecules can be described as the fusion of three <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> rings. The molecule is both rigid and virtually stress-free. Adamantane is the most stable isomer of C<sub>10</sub>H<sub>16</sub>. The spatial arrangement of <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms in the adamantane molecule is the same as in the <a href="/wiki/Diamond" title="Diamond">diamond</a> crystal. This similarity led to the name <i>adamantane</i>, which is derived from the Greek <i>adamantinos</i> (relating to <a href="/wiki/Steel" title="Steel">steel</a> or <a href="/wiki/Diamond" title="Diamond">diamond</a>).<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is a white solid with a <a href="/wiki/Camphor" title="Camphor">camphor</a>-like odor. It is the simplest <a href="/wiki/Diamondoid" title="Diamondoid">diamondoid</a>. </p><p>The discovery of adamantane in <a href="/wiki/Petroleum" title="Petroleum">petroleum</a> in 1933 launched a new field of chemistry dedicated to the synthesis and properties of polyhedral organic compounds. Adamantane derivatives have found practical application as drugs, polymeric materials, and thermally stable lubricants. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History_and_synthesis">History and synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=1" title="Edit section: History and synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1924, H. Decker suggested the existence of adamantane, which he called <b>decaterpene</b>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The first attempted laboratory synthesis was made in 1924 by German chemist <a href="/wiki/Hans_Meerwein" title="Hans Meerwein">Hans Meerwein</a> using the reaction of <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> with <a href="/wiki/Diethyl_malonate" title="Diethyl malonate">diethyl malonate</a> in the presence of <a href="/wiki/Piperidine" title="Piperidine">piperidine</a>. Instead of adamantane, Meerwein obtained 1,3,5,7-tetracarbomethoxybicyclo[3.3.1]nonane-2,6-dione: this compound, later named Meerwein's ester, was used in the synthesis of adamantane and its derivatives.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> D. Bottger tried to obtain adamantane using Meerwein's ester as precursor. The product, tricyclo-[3.3.1.1<sup>3,7</sup>], was not adamantane, but a derivative.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Other researchers attempted to synthesize adamantane using <a href="/wiki/Phloroglucinol" title="Phloroglucinol">phloroglucinol</a> and derivatives of <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a>, but also failed.<sup id="cite_ref-cr64_8-0" class="reference"><a href="#cite_note-cr64-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Meerweins_Ether.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Meerweins_Ether.png/170px-Meerweins_Ether.png" decoding="async" width="170" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Meerweins_Ether.png/255px-Meerweins_Ether.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/Meerweins_Ether.png/340px-Meerweins_Ether.png 2x" data-file-width="2683" data-file-height="1516" /></a><figcaption>Meerwein's ester</figcaption></figure> <p>Adamantane was first synthesized by <a href="/wiki/Vladimir_Prelog" title="Vladimir Prelog">Vladimir Prelog</a> in 1941 from Meerwein's ester.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> With a yield of 0.16%, the five-stage process was impractical (simplified in the image below). The method is used to synthesize certain derivatives of adamantane.<sup id="cite_ref-cr64_8-1" class="reference"><a href="#cite_note-cr64-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantane_synthesis_by_Prelog.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Adamantane_synthesis_by_Prelog.png/600px-Adamantane_synthesis_by_Prelog.png" decoding="async" width="600" height="323" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Adamantane_synthesis_by_Prelog.png/900px-Adamantane_synthesis_by_Prelog.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Adamantane_synthesis_by_Prelog.png/1200px-Adamantane_synthesis_by_Prelog.png 2x" data-file-width="3359" data-file-height="1806" /></a><figcaption></figcaption></figure> <p>Prelog's method was refined in 1956. The <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> yield was increased by the addition of the Hunsdiecker pathway (11%) and the Hoffman reaction (24%) that raised the total yield to 6.5%.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The process was still too complex, and a more convenient method was found in 1957 by <a href="/wiki/Paul_von_Ragu%C3%A9_Schleyer" title="Paul von Ragué Schleyer">Paul von Ragué Schleyer</a>: <a href="/wiki/Dicyclopentadiene" title="Dicyclopentadiene">dicyclopentadiene</a> was first <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenated</a> in the presence of a catalyst (e.g. <a href="/wiki/Adams%27_catalyst" title="Adams' catalyst">platinum dioxide</a>) to give <a href="/wiki/Tricyclodecane" title="Tricyclodecane">tricyclodecane</a> and then transformed into adamantane using a <a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis acid</a> (e.g. <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a>) as another catalyst. This method increased the yield to 30–40% and provided an affordable source of adamantane; it therefore stimulated characterization of adamantane and is still used in laboratory practice.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> The adamantane synthesis yield was later increased to 60%<sup id="cite_ref-app_15-0" class="reference"><a href="#cite_note-app-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> and 98% by <a href="/wiki/Ultrasound" title="Ultrasound">ultrasound</a> and <a href="/wiki/Superacid" title="Superacid">superacid</a> catalysis.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Today, adamantane is an affordable chemical compound with a cost of one or two <a href="/wiki/United_States_dollar" title="United States dollar">USD</a> per gram. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantane_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/Adamantane_synthesis.png/600px-Adamantane_synthesis.png" decoding="async" width="600" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/Adamantane_synthesis.png/900px-Adamantane_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4d/Adamantane_synthesis.png/1200px-Adamantane_synthesis.png 2x" data-file-width="5569" data-file-height="1069" /></a><figcaption></figcaption></figure> <p>All the above methods yield adamantane as a polycrystalline powder. Using this powder, single crystals can be grown from the melt, solution, or vapor phase (e.g. with the <a href="/wiki/Bridgman%E2%80%93Stockbarger_technique" class="mw-redirect" title="Bridgman–Stockbarger technique">Bridgman–Stockbarger technique</a>). Melt growth results in the worst crystalline quality with a mosaic spread in the X-ray reflection of about 1°. The best crystals are obtained from the liquid phase, but the growth is impracticably slow – several months for a 5–10 mm crystal. Growth from the vapor phase is a reasonable compromise in terms of speed and quality.<sup id="cite_ref-lowt_17-0" class="reference"><a href="#cite_note-lowt-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Adamantane is sublimed in a quartz tube placed in a furnace, which is equipped with several heaters maintaining a certain temperature gradient (about 10 °C/cm for adamantane) along the tube. Crystallization starts at one end of the tube, which is kept near the freezing point of adamantane. Slow cooling of the tube, while maintaining the temperature gradient, gradually shifts the melting zone (rate ~2 mm/hour), producing a single-crystal <a href="/wiki/Boule_(crystal)" title="Boule (crystal)">boule</a>.<sup id="cite_ref-hard_18-0" class="reference"><a href="#cite_note-hard-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Adamantane_spin.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Adamantane_spin.gif/220px-Adamantane_spin.gif" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Adamantane_spin.gif/330px-Adamantane_spin.gif 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Adamantane_spin.gif/440px-Adamantane_spin.gif 2x" data-file-width="480" data-file-height="480" /></a><figcaption><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick_model</a>, black carbon, white hydrogen</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=2" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adamantane was first isolated from petroleum by the Czech chemists S. Landa, V. Machacek, and M. Mzourek.<sup id="cite_ref-landa_19-0" class="reference"><a href="#cite_note-landa-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> They used <a href="/wiki/Fractional_distillation" title="Fractional distillation">fractional distillation</a> of petroleum. They could produce only a few milligrams of adamantane, but noticed its high boiling and <a href="/wiki/Melting_point" title="Melting point">melting points</a>. Because of the (assumed) similarity of its structure to that of diamond, the new compound was named adamantane.<sup id="cite_ref-cr64_8-2" class="reference"><a href="#cite_note-cr64-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Petroleum remains a source of adamantane; the content varies from between 0.0001% and 0.03% depending on the oil field and is too low for commercial production.<sup id="cite_ref-msu_pr_21-0" class="reference"><a href="#cite_note-msu_pr-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-bagriy_2_22-0" class="reference"><a href="#cite_note-bagriy_2-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Petroleum contains more than thirty derivatives of adamantane.<sup id="cite_ref-msu_pr_21-1" class="reference"><a href="#cite_note-msu_pr-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Their isolation from a complex mixture of hydrocarbons is possible due to their high melting point and the ability to distill with water vapor and form stable <a href="/wiki/Adduct" title="Adduct">adducts</a> with <a href="/wiki/Thiourea" title="Thiourea">thiourea</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Physical_properties">Physical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=3" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pure adamantane is a colorless, crystalline solid with a characteristic <a href="/wiki/Camphor" title="Camphor">camphor</a> smell. It is practically insoluble in water, but readily soluble in nonpolar <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvents</a>.<sup id="cite_ref-himicheskaya_entsiklopediya_23-0" class="reference"><a href="#cite_note-himicheskaya_entsiklopediya-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Adamantane has an unusually high <a href="/wiki/Melting_point" title="Melting point">melting point</a> for a <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>. At 270 °C, its melting point is much higher than other hydrocarbons with the same molecular weight, such as <a href="/wiki/Camphene" title="Camphene">camphene</a> (45 °C), <a href="/wiki/Limonene" title="Limonene">limonene</a> (−74 °C), <a href="/wiki/Ocimene" title="Ocimene">ocimene</a> (50 °C), <a href="/wiki/Terpinene" title="Terpinene">terpinene</a> (60 °C) or <a href="/wiki/Twistane" title="Twistane">twistane</a> (164 °C), or than a linear C<sub>10</sub>H<sub>22</sub> hydrocarbon <a href="/wiki/Decane" title="Decane">decane</a> (−28 °C). However, adamantane slowly <a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">sublimes</a> even at room temperature.<sup id="cite_ref-j1_24-0" class="reference"><a href="#cite_note-j1-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Adamantane can be <a href="/wiki/Steam_distillation" title="Steam distillation">distilled with water vapor</a>.<sup id="cite_ref-bagriy_2_22-1" class="reference"><a href="#cite_note-bagriy_2-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Structure">Structure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=4" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Adamantane_angles_bond-lengths.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Adamantane_angles_bond-lengths.png/220px-Adamantane_angles_bond-lengths.png" decoding="async" width="220" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/2/29/Adamantane_angles_bond-lengths.png 1.5x" data-file-width="298" data-file-height="245" /></a><figcaption>Bond lengths and angles of adamantane.</figcaption></figure> <p>As deduced by <a href="/wiki/Electron_diffraction" title="Electron diffraction">electron diffraction</a> and <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>, the molecule has <a href="/wiki/Tetrahedral_symmetry" title="Tetrahedral symmetry">T<sub>d</sub> symmetry</a>. The carbon–carbon bond lengths are 1.54 <a href="/wiki/Angstrom" title="Angstrom">Å</a>, almost identical to that of diamond. The carbon–hydrogen distances are 1.112 Å.<sup id="cite_ref-bagriy_1_3-1" class="reference"><a href="#cite_note-bagriy_1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>At ambient conditions, adamantane crystallizes in a face-centered cubic structure (<a href="/wiki/Space_group" title="Space group">space group</a> Fm3m, <i>a</i> = 9.426 ± 0.008 <a href="/wiki/Angstrom" title="Angstrom">Å</a>, four molecules in the unit cell) containing orientationally disordered adamantane molecules. This structure transforms into an ordered, primitive, <a href="/wiki/Tetragonal" class="mw-redirect" title="Tetragonal">tetragonal</a> phase (<i>a</i> = 6.641 <a href="/wiki/Angstrom" title="Angstrom">Å</a>, <i>c</i> = 8.875 <a href="/wiki/Angstrom" title="Angstrom">Å</a>) with two molecules per cell, either upon cooling to 208 K or pressurizing to above 0.5 GPa.<sup id="cite_ref-cr64_8-3" class="reference"><a href="#cite_note-cr64-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-j1_24-1" class="reference"><a href="#cite_note-j1-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>This <a href="/wiki/Phase_transition" title="Phase transition">phase transition</a> is of the first order; it is accompanied by an anomaly in the <a href="/wiki/Heat_capacity" title="Heat capacity">heat capacity</a>, elastic, and other properties. In particular, whereas adamantane molecules freely rotate in the cubic phase, they are frozen in the tetragonal one; the density increases stepwise from 1.08 to 1.18 g/cm<sup>3</sup>, and the <a href="/wiki/Entropy" title="Entropy">entropy</a> changes by a significant amount of 1594 J/(mol·K).<sup id="cite_ref-lowt_17-1" class="reference"><a href="#cite_note-lowt-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hardness">Hardness</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=5" title="Edit section: Hardness"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Elastic constants of adamantane were measured using large (centimeter-sized) single crystals and the ultrasonic echo technique. The principal value of the <a href="/wiki/Elasticity_tensor" title="Elasticity tensor">elasticity tensor</a>, C<sub>11</sub>, was deduced as 7.52, 8.20, and 6.17 GPa for the <110>, <111>, and <100> crystalline directions.<sup id="cite_ref-hard_18-1" class="reference"><a href="#cite_note-hard-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> For comparison, the corresponding values for crystalline diamond are 1161, 1174, and 1123 GPa.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> The arrangement of carbon atoms is the same in adamantane and diamond;<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> however, in the adamantane solid, molecules do not form a covalent lattice as in diamond, but interact through weak <a href="/wiki/Van_der_Waals_force" title="Van der Waals force">van der Waals forces</a>. As a result, adamantane crystals are very soft and plastic.<sup id="cite_ref-lowt_17-2" class="reference"><a href="#cite_note-lowt-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-hard_18-2" class="reference"><a href="#cite_note-hard-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Spectroscopy">Spectroscopy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=6" title="Edit section: Spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">nuclear magnetic resonance</a> (NMR) spectrum of adamantane consists of two poorly resolved signals, which correspond to sites 1 and 2 (see picture below). The <sup>1</sup>H and <sup>13</sup>C NMR chemical shifts are respectively 1.873 and 1.756 ppm and are 28.46 and 37.85 ppm.<sup id="cite_ref-sdbs_28-0" class="reference"><a href="#cite_note-sdbs-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The simplicity of these spectra is consistent with high molecular symmetry. </p><p><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectra</a> of adamantane and its derivatives are rather characteristic. The main peak at <i>m</i>/<i>z</i> = 136 corresponds to the <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">10</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">16</sub></span></span></span> ion. Its fragmentation results in weaker signals as <i>m</i>/<i>z</i> = 93, 80, 79, 67, 41 and 39.<sup id="cite_ref-bagriy_1_3-2" class="reference"><a href="#cite_note-bagriy_1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-sdbs_28-1" class="reference"><a href="#cite_note-sdbs-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared absorption spectrum</a> of adamantane is relatively simple because of the high symmetry of the molecule. The main absorption bands and their assignment are given in the table:<sup id="cite_ref-bagriy_1_3-3" class="reference"><a href="#cite_note-bagriy_1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th>Wavenumber, cm<sup>−1</sup> </th> <th>Assignment<sup>*</sup> </th></tr> <tr> <td>444 </td> <td>δ(CCC) </td></tr> <tr> <td>638 </td> <td>δ(CCC) </td></tr> <tr> <td>798 </td> <td>ν(C−C) </td></tr> <tr> <td>970 </td> <td>ρ(CH<sub>2</sub>), ν(C−C), δ(HCC) </td></tr> <tr> <td>1103 </td> <td>δ(HCC) </td></tr> <tr> <td>1312 </td> <td>ν(C−C), ω(CH<sub>2</sub>) </td></tr> <tr> <td>1356 </td> <td>δ(HCC), ω(CH<sub>2</sub>) </td></tr> <tr> <td>1458 </td> <td>δ(HCH) </td></tr> <tr> <td>2850 </td> <td>ν(C−H) in CH<sub>2</sub> groups </td></tr> <tr> <td>2910 </td> <td>ν(C−H) in CH<sub>2</sub> groups </td></tr> <tr> <td>2930 </td> <td>ν(C−H) in CH<sub>2</sub> groups </td></tr></tbody></table> <p><sup>*</sup> Legends correspond to types of oscillations: δ – deformation, ν – stretching, ρ and ω – out of plane deformation vibrations of CH<sub>2</sub> groups. </p> <div class="mw-heading mw-heading3"><h3 id="Optical_activity">Optical activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=7" title="Edit section: Optical activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adamantane derivatives with different substituents at every nodal carbon sites are <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Such optical activity was described in adamantane in 1969 with the four different substituents being <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <a href="/wiki/Bromine" title="Bromine">bromine</a>, <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>, and <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl</a>. The values of <a href="/wiki/Specific_rotation" title="Specific rotation">specific rotation</a> are small and are usually within 1°.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=8" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Using the rules of systematic nomenclature, adamantane is called tricyclo[3.3.1.1<sup>3,7</sup>]decane. However, <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> recommends using the name "adamantane".<sup id="cite_ref-iupac2013_1-1" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-left" typeof="mw:File"><a href="/wiki/File:Adamantane_numbering.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Adamantane_numbering.svg/100px-Adamantane_numbering.svg.png" decoding="async" width="100" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Adamantane_numbering.svg/150px-Adamantane_numbering.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Adamantane_numbering.svg/200px-Adamantane_numbering.svg.png 2x" data-file-width="200" data-file-height="200" /></a><figcaption></figcaption></figure> <p>The adamantane molecule is composed of only carbon and hydrogen and has T<sub>d</sub> symmetry. Therefore, its 16 hydrogen and 10 carbon atoms can be described by only two sites, which are labeled in the figure as <b>1</b> (4 equivalent sites) and <b>2</b> (6 equivalent sites). </p><p>Structural relatives of adamantane are <a href="/w/index.php?title=Noradamantane&action=edit&redlink=1" class="new" title="Noradamantane (page does not exist)">noradamantane</a> and <a href="/w/index.php?title=Homoadamantane&action=edit&redlink=1" class="new" title="Homoadamantane (page does not exist)">homoadamantane</a>, which respectively contain one less and one more CH<sub>2</sub> link than the adamantane. </p><p>The <a href="/wiki/Functional_group" title="Functional group">functional group</a> derived from adamantane is adamantyl, formally named as 1-adamantyl or 2-adamantyl depending on which site is connected to the parent molecule. Adamantyl groups are a bulky <a href="/wiki/Pendant_group" title="Pendant group">pendant group</a> used to improve the thermal and mechanical properties of polymers.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_properties">Chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=9" title="Edit section: Chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Adamantane_cations">Adamantane cations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=10" title="Edit section: Adamantane cations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The adamantane cation can be produced by treating 1-fluoro-adamantane with SbF<sub>5</sub>. Its stability is relatively high.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Dication" title="Dication">dication</a> of 1,3-didehydroadamantane was obtained in solutions of <a href="/wiki/Superacid" title="Superacid">superacids</a>. It also has elevated stability due to the phenomenon called "three-dimensional aromaticity"<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Homoaromaticity" title="Homoaromaticity">homoaromaticity</a>.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> This <a href="/wiki/Four-center_two-electron_bond" title="Four-center two-electron bond">four-center two-electron bond</a> involves one pair of electrons delocalized among the four bridgehead atoms. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantane_dication.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Adamantane_dication.png/500px-Adamantane_dication.png" decoding="async" width="500" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Adamantane_dication.png/750px-Adamantane_dication.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Adamantane_dication.png/1000px-Adamantane_dication.png 2x" data-file-width="5042" data-file-height="1245" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Reactions">Reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=11" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most reactions of adamantane occur via the 3-coordinated carbon sites. They are involved in the reaction of adamantane with concentrated <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> which produces <a href="/wiki/Adamantanone" title="Adamantanone">adamantanone</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantanone_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Adamantanone_synthesis.png/420px-Adamantanone_synthesis.png" decoding="async" width="420" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Adamantanone_synthesis.png/630px-Adamantanone_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/Adamantanone_synthesis.png/840px-Adamantanone_synthesis.png 2x" data-file-width="3295" data-file-height="936" /></a><figcaption></figcaption></figure> <p>The <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl group</a> of adamantanone allows further reactions via the bridging site. For example, adamantanone is the starting compound for obtaining such derivatives of adamantane as 2-adamantanecarbonitrile<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> and 2-methyl-adamantane.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Bromination">Bromination</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=12" title="Edit section: Bromination"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adamantane readily reacts with various brominating agents, including molecular <a href="/wiki/Bromine" title="Bromine">bromine</a>. The composition and the ratio of the reaction products depend on the reaction conditions and especially the presence and type of <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a>.<sup id="cite_ref-msu_pr_21-2" class="reference"><a href="#cite_note-msu_pr-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantane_bromination.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Adamantane_bromination.png/600px-Adamantane_bromination.png" decoding="async" width="600" height="287" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Adamantane_bromination.png/900px-Adamantane_bromination.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Adamantane_bromination.png/1200px-Adamantane_bromination.png 2x" data-file-width="3000" data-file-height="1434" /></a><figcaption></figcaption></figure> <p>Boiling of adamantane with bromine results in a monosubstituted adamantane, 1-bromadamantane. Multiple substitution with bromine is achieved by adding a <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> catalyst.<sup id="cite_ref-nesmeyanov_41-0" class="reference"><a href="#cite_note-nesmeyanov-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>The rate of bromination is accelerated upon addition of Lewis acids and is unchanged by irradiation or addition of free radicals. This indicates that the reaction occurs via an ionic mechanism.<sup id="cite_ref-cr64_8-4" class="reference"><a href="#cite_note-cr64-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Fluorination">Fluorination</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=13" title="Edit section: Fluorination"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first fluorinations of adamantane were conducted using 1-hydroxyadamantane<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> and 1-aminoadamantane as initial compounds. Later, fluorination was achieved starting from adamantane itself.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> In all these cases, reaction proceeded via formation of the adamantane cation which then interacted with fluorinated nucleophiles. Fluorination of adamantane with gaseous <a href="/wiki/Fluorine" title="Fluorine">fluorine</a> has also been reported.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Carboxylation">Carboxylation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=14" title="Edit section: Carboxylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylation of adamantane with formic acid gives <a href="/wiki/1-Adamantanecarboxylic_acid" title="1-Adamantanecarboxylic acid">1-adamantanecarboxylic acid</a>.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Adamantane_caboxylic_acid_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Adamantane_caboxylic_acid_synthesis.png/500px-Adamantane_caboxylic_acid_synthesis.png" decoding="async" width="500" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Adamantane_caboxylic_acid_synthesis.png/750px-Adamantane_caboxylic_acid_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Adamantane_caboxylic_acid_synthesis.png/1000px-Adamantane_caboxylic_acid_synthesis.png 2x" data-file-width="4357" data-file-height="858" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Oxidation">Oxidation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=15" title="Edit section: Oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1-Hydroxyadamantane is readily formed by hydrolysis of 1-bromadamantane in aqueous solution of <a href="/wiki/Acetone" title="Acetone">acetone</a>. It can also be produced by <a href="/wiki/Ozonation" class="mw-redirect" title="Ozonation">ozonation</a> of the adamantane:<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Oxidation of the alcohol gives <a href="/wiki/Adamantanone" title="Adamantanone">adamantanone</a>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:1-Adamantanol_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/1-Adamantanol_synthesis.svg/440px-1-Adamantanol_synthesis.svg.png" decoding="async" width="440" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/1-Adamantanol_synthesis.svg/660px-1-Adamantanol_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/1-Adamantanol_synthesis.svg/880px-1-Adamantanol_synthesis.svg.png 2x" data-file-width="2070" data-file-height="319" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Others">Others</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=16" title="Edit section: Others"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adamantane interacts with <a href="/wiki/Benzene" title="Benzene">benzene</a> in the presence of Lewis acids, resulting in a <a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reaction</a>.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Aryl-substituted adamantane derivatives can be easily obtained starting from 1-hydroxyadamantane. In particular, the reaction with <a href="/wiki/Anisole" title="Anisole">anisole</a> proceeds under normal conditions and does not require a catalyst.<sup id="cite_ref-nesmeyanov_41-1" class="reference"><a href="#cite_note-nesmeyanov-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Nitration of adamantane is a difficult reaction characterized by moderate yields.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> A nitrogen-substituted drug <a href="/wiki/Amantadine" title="Amantadine">amantadine</a> can be prepared by reacting adamantane with bromine or <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> to give the bromide or nitroester at the 1-position. Reaction of either compound with <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a> affords the acetamide, which is hydrolyzed to give 1-adamantylamine:<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Preparation_of_amantadine.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Preparation_of_amantadine.png/800px-Preparation_of_amantadine.png" decoding="async" width="800" height="232" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Preparation_of_amantadine.png/1200px-Preparation_of_amantadine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Preparation_of_amantadine.png/1600px-Preparation_of_amantadine.png 2x" data-file-width="5338" data-file-height="1548" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=17" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adamantane itself enjoys few applications since it is merely an unfunctionalized <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>. It is used in some <a href="/wiki/Dry_etching" title="Dry etching">dry etching</a> masks<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Polymer" title="Polymer">polymer</a> formulations. </p><p>In <a href="/wiki/Solid-state_NMR" class="mw-redirect" title="Solid-state NMR">solid-state NMR</a> spectroscopy, adamantane is a common standard for <a href="/wiki/Chemical_shift" title="Chemical shift">chemical shift</a> referencing.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Dye_laser" title="Dye laser">dye lasers</a>, adamantane may be used to extend the life of the gain medium; it cannot be <a href="/wiki/Photoionisation" class="mw-redirect" title="Photoionisation">photoionized</a> under atmosphere because its absorption bands lie in the <a href="/wiki/Vacuum_UV" class="mw-redirect" title="Vacuum UV">vacuum-ultraviolet</a> region of the spectrum. Photoionization energies have been determined for adamantane as well as for several bigger <a href="/wiki/Diamondoids" class="mw-redirect" title="Diamondoids">diamondoids</a>.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="In_medicine">In medicine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=18" title="Edit section: In medicine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>All medical applications known so far involve not pure adamantane, but its derivatives. The first adamantane derivative used as a drug was <a href="/wiki/Amantadine" title="Amantadine">amantadine</a> – first (1967) as an <a href="/wiki/Antiviral_drug" title="Antiviral drug">antiviral drug</a> against various strains of <a href="/wiki/Influenza" title="Influenza">influenza</a><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> and then to treat <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid15800186_55-0" class="reference"><a href="#cite_note-pmid15800186-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> Other drugs among adamantane derivatives include <a href="/wiki/Adapalene" title="Adapalene">adapalene</a>, <a href="/wiki/Adapromine" title="Adapromine">adapromine</a>, <a href="/wiki/Bromantane" title="Bromantane">bromantane</a> (bromantan), <a href="/wiki/Carmantadine" title="Carmantadine">carmantadine</a>, <a href="/wiki/Chlodantane" title="Chlodantane">chlodantane</a> (chlodantan), <a href="/wiki/Dopamantine" title="Dopamantine">dopamantine</a>, <a href="/wiki/Gludantan" title="Gludantan">gludantan</a> (gludantane), <a href="/wiki/Hemantane" title="Hemantane">hemantane</a> (hymantane), <a href="/wiki/Idramantone" title="Idramantone">idramantone</a> (kemantane), <a href="/wiki/Memantine" title="Memantine">memantine</a>, <a href="/wiki/Nitromemantine" title="Nitromemantine">nitromemantine</a> <a href="/wiki/Rimantadine" title="Rimantadine">rimantadine</a>, <a href="/wiki/Saxagliptin" title="Saxagliptin">saxagliptin</a>, <a href="/wiki/Somantadine" title="Somantadine">somantadine</a>, <a href="/wiki/Tromantadine" title="Tromantadine">tromantadine</a>, and <a href="/wiki/Vildagliptin" title="Vildagliptin">vildagliptin</a>. <a href="/wiki/Polymer" title="Polymer">Polymers</a> of adamantane have been patented as antiviral agents against <a href="/wiki/HIV" title="HIV">HIV</a>.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>Influenza virus strains have developed <a href="/wiki/Drug_resistance" title="Drug resistance">drug resistance</a> to amantadine and rimantadine, which are not effective against prevalent strains as of 2016. </p> <ul class="gallery mw-gallery-traditional center"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Adapalene_structure.svg" class="mw-file-description" title="Adapalene"><img alt="Adapalene" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Adapalene_structure.svg/120px-Adapalene_structure.svg.png" decoding="async" width="120" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Adapalene_structure.svg/180px-Adapalene_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Adapalene_structure.svg/240px-Adapalene_structure.svg.png 2x" data-file-width="512" data-file-height="407" /></a></span></div> <div class="gallerytext"><a href="/wiki/Adapalene" title="Adapalene">Adapalene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Adapromine.svg" class="mw-file-description" title="Adapromine"><img alt="Adapromine" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Adapromine.svg/108px-Adapromine.svg.png" decoding="async" width="108" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Adapromine.svg/162px-Adapromine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Adapromine.svg/216px-Adapromine.svg.png 2x" data-file-width="512" data-file-height="570" /></a></span></div> <div class="gallerytext"><a href="/wiki/Adapromine" title="Adapromine">Adapromine</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Amantadine.svg" class="mw-file-description" title="Amantadine"><img alt="Amantadine" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Amantadine.svg/85px-Amantadine.svg.png" decoding="async" width="85" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Amantadine.svg/128px-Amantadine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Amantadine.svg/171px-Amantadine.svg.png 2x" data-file-width="512" data-file-height="719" /></a></span></div> <div class="gallerytext"><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Bromantane_structure.svg" class="mw-file-description" title="Bromantane"><img alt="Bromantane" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Bromantane_structure.svg/120px-Bromantane_structure.svg.png" decoding="async" width="120" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Bromantane_structure.svg/180px-Bromantane_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Bromantane_structure.svg/240px-Bromantane_structure.svg.png 2x" data-file-width="512" data-file-height="257" /></a></span></div> <div class="gallerytext"><a href="/wiki/Bromantane" title="Bromantane">Bromantane</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Memantine_acsv.svg" class="mw-file-description" title="Memantine"><img alt="Memantine" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Memantine_acsv.svg/107px-Memantine_acsv.svg.png" decoding="async" width="107" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Memantine_acsv.svg/160px-Memantine_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Memantine_acsv.svg/214px-Memantine_acsv.svg.png 2x" data-file-width="598" data-file-height="672" /></a></span></div> <div class="gallerytext"><a href="/wiki/Memantine" title="Memantine">Memantine</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Rimantadine.svg" class="mw-file-description" title="Rimantadine"><img alt="Rimantadine" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Rimantadine.svg/85px-Rimantadine.svg.png" decoding="async" width="85" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Rimantadine.svg/127px-Rimantadine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Rimantadine.svg/170px-Rimantadine.svg.png 2x" data-file-width="512" data-file-height="723" /></a></span></div> <div class="gallerytext"><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Saxagliptin.svg" class="mw-file-description" title="Saxagliptin"><img alt="Saxagliptin" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Saxagliptin.svg/120px-Saxagliptin.svg.png" decoding="async" width="120" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Saxagliptin.svg/180px-Saxagliptin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Saxagliptin.svg/240px-Saxagliptin.svg.png 2x" data-file-width="590" data-file-height="363" /></a></span></div> <div class="gallerytext"><a href="/wiki/Saxagliptin" title="Saxagliptin">Saxagliptin</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Tromantadine.svg" class="mw-file-description" title="Tromantadine"><img alt="Tromantadine" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Tromantadine.svg/120px-Tromantadine.svg.png" decoding="async" width="120" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Tromantadine.svg/180px-Tromantadine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Tromantadine.svg/240px-Tromantadine.svg.png 2x" data-file-width="512" data-file-height="354" /></a></span></div> <div class="gallerytext"><a href="/wiki/Tromantadine" title="Tromantadine">Tromantadine</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Vildagliptin.svg" class="mw-file-description" title="Vildagliptin"><img alt="Vildagliptin" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Vildagliptin.svg/120px-Vildagliptin.svg.png" decoding="async" width="120" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Vildagliptin.svg/180px-Vildagliptin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Vildagliptin.svg/240px-Vildagliptin.svg.png 2x" data-file-width="512" data-file-height="305" /></a></span></div> <div class="gallerytext"><a href="/wiki/Vildagliptin" title="Vildagliptin">Vildagliptin</a></div> </li> </ul> <div class="mw-heading mw-heading3"><h3 id="In_designer_drugs">In designer drugs</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=19" title="Edit section: In designer drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adamantane was recently identified as a key structural subunit in several synthetic <a href="/wiki/Cannabinoid" title="Cannabinoid">cannabinoid</a> <a href="/wiki/Designer_drug" title="Designer drug">designer drugs</a>, namely <a href="/wiki/AB-001" title="AB-001">AB-001</a> and <a href="/wiki/SDB-001" class="mw-redirect" title="SDB-001">SDB-001</a>.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Spacecraft_propellant">Spacecraft propellant</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=20" title="Edit section: Spacecraft propellant"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adamantane is an attractive candidate for propellant in <a href="/wiki/Hall-effect_thruster" title="Hall-effect thruster">Hall-effect thrusters</a> because it ionizes easily, can be stored in solid form rather than a heavy pressure tank, and is relatively nontoxic.<sup id="cite_ref-ais_58-0" class="reference"><a href="#cite_note-ais-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Potential_technological_applications">Potential technological applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=21" title="Edit section: Potential technological applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some alkyl derivatives of adamantane have been used as a working fluid in <a href="/wiki/Hydraulic_cylinder" title="Hydraulic cylinder">hydraulic systems</a>.<sup id="cite_ref-krugosvet_59-0" class="reference"><a href="#cite_note-krugosvet-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> Adamantane-based polymers might find application for coatings of <a href="/wiki/Touchscreen" title="Touchscreen">touchscreens</a>,<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> and there are prospects for using adamantane and its homologues in <a href="/wiki/Nanotechnology" title="Nanotechnology">nanotechnology</a>. For example, the soft cage-like structure of adamantane solid allows incorporation of guest molecules, which can be released inside the human body upon breaking the matrix.<sup id="cite_ref-app_15-1" class="reference"><a href="#cite_note-app-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> Adamantane could be used as molecular building blocks for self-assembly of molecular crystals.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Adamantane_analogues">Adamantane analogues</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=22" title="Edit section: Adamantane analogues"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many molecules and ions adopt adamantane-like cage structures. Those include <a href="/wiki/Phosphorus_trioxide" title="Phosphorus trioxide">phosphorus trioxide</a> P<sub>4</sub>O<sub>6</sub>, <a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">arsenic trioxide</a> As<sub>4</sub>O<sub>6</sub>, <a href="/wiki/Phosphorus_pentoxide" title="Phosphorus pentoxide">phosphorus pentoxide</a> P<sub>4</sub>O<sub>10</sub> = (PO)<sub>4</sub>O<sub>6</sub>, <a href="/wiki/Phosphorus_pentasulfide" title="Phosphorus pentasulfide">phosphorus pentasulfide</a> P<sub>4</sub>S<sub>10</sub> = (PS)<sub>4</sub>S<sub>6</sub>, and <a href="/wiki/Hexamethylenetetramine" title="Hexamethylenetetramine">hexamethylenetetramine</a> C<sub>6</sub>N<sub>4</sub>H<sub>12</sub> = N<sub>4</sub>(CH<sub>2</sub>)<sub>6</sub>.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Particularly notorious is <a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">tetramethylenedisulfotetramine</a>, often shortened to "tetramine", a <a href="/wiki/Rodenticide" title="Rodenticide">rodenticide</a> banned in most countries for extreme toxicity to humans. The silicon analogue of adamantane, sila-adamantane, was synthesized in 2005.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Arsenicin_A" title="Arsenicin A">Arsenicin A</a> is a naturally occurring <a href="/wiki/Organoarsenic_chemistry" title="Organoarsenic chemistry">organoarsenic</a> chemical isolated from the <a href="/wiki/New_Caledonia" title="New Caledonia">New Caledonian</a> <a href="/wiki/Sea_sponge" class="mw-redirect" title="Sea sponge">sea sponge</a> <i>Echinochalina bargibanti</i> and is the first known heterocycle to contain multiple arsenic atoms.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bagno_67-0" class="reference"><a href="#cite_note-Bagno-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Guella_68-0" class="reference"><a href="#cite_note-Guella-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-traditional center"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Adamantane_acsv.svg" class="mw-file-description" title="Adamantane"><img alt="Adamantane" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Adamantane_acsv.svg/120px-Adamantane_acsv.svg.png" decoding="async" width="120" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Adamantane_acsv.svg/180px-Adamantane_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Adamantane_acsv.svg/240px-Adamantane_acsv.svg.png 2x" data-file-width="463" data-file-height="419" /></a></span></div> <div class="gallerytext">Adamantane</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Hexamine.svg" class="mw-file-description" title="Hexamethylenetetramine"><img alt="Hexamethylenetetramine" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hexamine.svg/120px-Hexamine.svg.png" decoding="async" width="120" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hexamine.svg/180px-Hexamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hexamine.svg/240px-Hexamine.svg.png 2x" data-file-width="220" data-file-height="200" /></a></span></div> <div class="gallerytext"><a href="/wiki/Hexamethylenetetramine" title="Hexamethylenetetramine">Hexamethylenetetramine</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Phosphorus-pentoxide-2D-dimensions.svg" class="mw-file-description" title="Phosphorus pentoxide"><img alt="Phosphorus pentoxide" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Phosphorus-pentoxide-2D-dimensions.svg/119px-Phosphorus-pentoxide-2D-dimensions.svg.png" decoding="async" width="119" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Phosphorus-pentoxide-2D-dimensions.svg/179px-Phosphorus-pentoxide-2D-dimensions.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Phosphorus-pentoxide-2D-dimensions.svg/238px-Phosphorus-pentoxide-2D-dimensions.svg.png 2x" data-file-width="1093" data-file-height="1100" /></a></span></div> <div class="gallerytext"><a href="/wiki/Phosphorus_pentoxide" title="Phosphorus pentoxide">Phosphorus pentoxide</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Phosphorus-pentasulfide-2D-dimensions.png" class="mw-file-description" title="Phosphorus pentasulfide"><img alt="Phosphorus pentasulfide" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Phosphorus-pentasulfide-2D-dimensions.png/118px-Phosphorus-pentasulfide-2D-dimensions.png" decoding="async" width="118" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Phosphorus-pentasulfide-2D-dimensions.png/178px-Phosphorus-pentasulfide-2D-dimensions.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Phosphorus-pentasulfide-2D-dimensions.png/237px-Phosphorus-pentasulfide-2D-dimensions.png 2x" data-file-width="1086" data-file-height="1100" /></a></span></div> <div class="gallerytext"><a href="/wiki/Phosphorus_pentasulfide" title="Phosphorus pentasulfide">Phosphorus pentasulfide</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Tetramethylenedisulfotetramine.png" class="mw-file-description" title="Tetramethylenedisulfotetramine"><img alt="Tetramethylenedisulfotetramine" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Tetramethylenedisulfotetramine.png/120px-Tetramethylenedisulfotetramine.png" decoding="async" width="120" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Tetramethylenedisulfotetramine.png/180px-Tetramethylenedisulfotetramine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Tetramethylenedisulfotetramine.png/240px-Tetramethylenedisulfotetramine.png 2x" data-file-width="3284" data-file-height="2912" /></a></span></div> <div class="gallerytext"><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Tetrodotoxin.svg" class="mw-file-description" title="Tetrodotoxin"><img alt="Tetrodotoxin" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Tetrodotoxin.svg/120px-Tetrodotoxin.svg.png" decoding="async" width="120" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Tetrodotoxin.svg/180px-Tetrodotoxin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Tetrodotoxin.svg/240px-Tetrodotoxin.svg.png 2x" data-file-width="620" data-file-height="345" /></a></span></div> <div class="gallerytext"><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Arsenicin_A.png" class="mw-file-description" title="Arsenicin A"><img alt="Arsenicin A" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Arsenicin_A.png/120px-Arsenicin_A.png" decoding="async" width="120" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Arsenicin_A.png/180px-Arsenicin_A.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/Arsenicin_A.png/240px-Arsenicin_A.png 2x" data-file-width="897" data-file-height="776" /></a></span></div> <div class="gallerytext"><a href="/wiki/Arsenicin_A" title="Arsenicin A">Arsenicin A</a></div> </li> </ul> <p>Conjoining adamantane cages produces higher <a href="/wiki/Diamondoids" class="mw-redirect" title="Diamondoids">diamondoids</a>, such as <a href="/wiki/Diamantane" title="Diamantane">diamantane</a> (C<sub>14</sub>H<sub>20</sub> – two fused adamantane cages), triamantane (C<sub>18</sub>H<sub>24</sub>), tetramantane (C<sub>22</sub>H<sub>28</sub>), pentamantane (C<sub>26</sub>H<sub>32</sub>), hexamantane (C<sub>26</sub>H<sub>30</sub>), etc. Their synthesis is similar to that of adamantane and like adamantane, they can also be extracted from petroleum, though at even much smaller yields. </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Adamantane&action=edit&section=23" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac2013_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac2013_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1"><i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. p. 169. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069-FP001">10.1039/9781849733069-FP001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>. <q>The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=169&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-FP001&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-r1-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-r1_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-r1_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-r1_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-r1_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-r1_2-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaynes,_William_M.2016" class="citation book cs1">Haynes, William M., ed. 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(1989). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=8RA2AAAAIAAJ"><i>Adamantanes: synthesis, properties, applications</i></a> (in Russian). Nauka. pp. <span class="nowrap">5–</span>57. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/5-02-001382-X" title="Special:BookSources/5-02-001382-X"><bdi>5-02-001382-X</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240308022541/https://books.google.com/books?id=8RA2AAAAIAAJ">Archived</a> from the original on 2024-03-08<span class="reference-accessdate">. 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(1973). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv5p0016">"Adamantane"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Adamantane&rft.date=1973&rft.au=Schleyer%2C+P.+von+R.&rft.au=Donaldson%2C+M.+M.&rft.au=Nicholas%2C+R.+D.&rft.au=Cupas%2C+C.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv5p0016&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 5, p. 16</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=16&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span>.</span> </li> <li id="cite_note-app-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-app_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-app_15-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMansoori,_G._Ali2007" class="citation book cs1">Mansoori, G. Ali (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0-FtXsmeX8oC&pg=PA50"><i>Molecular building blocks for nanotechnology: from diamondoids to nanoscale materials and applications</i></a>. Springer. pp. <span class="nowrap">48–</span>55. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-387-39937-9" title="Special:BookSources/978-0-387-39937-9"><bdi>978-0-387-39937-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Molecular+building+blocks+for+nanotechnology%3A+from+diamondoids+to+nanoscale+materials+and+applications&rft.pages=%3Cspan+class%3D%22nowrap%22%3E48-%3C%2Fspan%3E55&rft.pub=Springer&rft.date=2007&rft.isbn=978-0-387-39937-9&rft.au=Mansoori%2C+G.+Ali&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0-FtXsmeX8oC%26pg%3DPA50&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSteven_V._Ley,_Caroline_M.R._Low2012" class="citation book cs1">Steven V. Ley, Caroline M.R. Low (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=SRzrCAAAQBAJ&dq=high+yield+adamantane+synthesis&pg=PA90"><i>Ultrasound in Synthesis</i></a>. Springer. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-74672-7" title="Special:BookSources/978-3-642-74672-7"><bdi>978-3-642-74672-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230427083616/https://books.google.com/books?id=SRzrCAAAQBAJ&dq=high+yield+adamantane+synthesis&pg=PA90">Archived</a> from the original on 27 April 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">14 March</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Ultrasound+in+Synthesis&rft.pub=Springer&rft.date=2012-12-06&rft.isbn=978-3-642-74672-7&rft.au=Steven+V.+Ley%2C+Caroline+M.R.+Low&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DSRzrCAAAQBAJ%26dq%3Dhigh%2Byield%2Badamantane%2Bsynthesis%26pg%3DPA90&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-lowt-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-lowt_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-lowt_17-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-lowt_17-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWindsorSaundersonSherwoodTaylor1978" class="citation journal cs1">Windsor CG, Saunderson DH, Sherwood JN, Taylor D, Pawley GS (1978). 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"Sur l'adamantane, nouvel hydrocarbure extrait de naphte". <i>Collection of Czechoslovak Chemical Communications</i>. <b>5</b>: <span class="nowrap">1–</span>5. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1135%2Fcccc19330001">10.1135/cccc19330001</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Collection+of+Czechoslovak+Chemical+Communications&rft.atitle=Sur+l%27adamantane%2C+nouvel+hydrocarbure+extrait+de+naphte.&rft.volume=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E5&rft.date=1933&rft_id=info%3Adoi%2F10.1135%2Fcccc19330001&rft.au=Landa%2C+S.&rft.au=Mach%C3%A1cek%2C+V.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLandaABC1933" class="citation cs2">Landa, S., Machacek, V., Mzourek, M., Landa, M. 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Abstr.</i>, <b>27</b>: 5949</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Abstr.&rft.atitle=Title+unknown&rft.volume=27&rft.pages=5949&rft.date=1933&rft.au=Landa%2C+S.&rft.au=Machacek%2C+V.&rft.au=Mzourek%2C+M.&rft.au=Landa%2C+M.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJh8hAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-msu_pr-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-msu_pr_21-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-msu_pr_21-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-msu_pr_21-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1 cs1-prop-foreign-lang-source"><a rel="nofollow" class="external text" href="http://www.chem.msu.su/rus/teaching/oil/spezprakt-adam.html">"Synthesis of adamantane"</a> (in Russian). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120306233134/http://www.chem.msu.su/rus/teaching/oil/spezprakt-adam.html">Archived</a> from the original on 2012-03-06<span class="reference-accessdate">. Retrieved <span class="nowrap">2009-12-11</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Synthesis+of+adamantane&rft_id=http%3A%2F%2Fwww.chem.msu.su%2Frus%2Fteaching%2Foil%2Fspezprakt-adam.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span> Special practical problem for the students of IV year. Department of Petroleum Chemistry and Organic Catalysis <a href="/wiki/Moscow_State_University" title="Moscow State University">MSU</a>.</span> </li> <li id="cite_note-bagriy_2-22"><span class="mw-cite-backlink">^ <a href="#cite_ref-bagriy_2_22-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-bagriy_2_22-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBagriy_EI1989" class="citation book cs1">Bagriy EI (1989). 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"Elastic and Lattice Dynamical Properties of Textured Diamond Films". <i>Physica Status Solidi B</i>. <b>215</b> (1): <span class="nowrap">189–</span>192. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1999PSSBR.215..189A">1999PSSBR.215..189A</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F%28SICI%291521-3951%28199909%29215%3A1%3C189%3A%3AAID-PSSB189%3E3.0.CO%3B2-X">10.1002/(SICI)1521-3951(199909)215:1<189::AID-PSSB189>3.0.CO;2-X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physica+Status+Solidi+B&rft.atitle=Elastic+and+Lattice+Dynamical+Properties+of+Textured+Diamond+Films&rft.volume=215&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E189-%3C%2Fspan%3E192&rft.date=1999&rft_id=info%3Adoi%2F10.1002%2F%28SICI%291521-3951%28199909%29215%3A1%3C189%3A%3AAID-PSSB189%3E3.0.CO%3B2-X&rft_id=info%3Abibcode%2F1999PSSBR.215..189A&rft.au=Anastassakis%2C+E.&rft.au=Siakavellas%2C+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMansoori,_G._Ali2005" class="citation book cs1">Mansoori, G. Ali (2005). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/principlesofnano0000mans"><i>Principles of nanotechnology: molecular-based study of condensed matter in small systems</i></a></span>. World Scientific. p. <a rel="nofollow" class="external text" href="https://archive.org/details/principlesofnano0000mans/page/12">12</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/981-256-154-4" title="Special:BookSources/981-256-154-4"><bdi>981-256-154-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+nanotechnology%3A+molecular-based+study+of+condensed+matter+in+small+systems&rft.pages=12&rft.pub=World+Scientific&rft.date=2005&rft.isbn=981-256-154-4&rft.au=Mansoori%2C+G.+Ali&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fprinciplesofnano0000mans&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWright,_John_Dalton1995" class="citation book cs1">Wright, John Dalton (1995). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7sroAgMASIEC&pg=PA28"><i>Molecular crystals</i></a>. Cambridge University Press. p. 28. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-521-47730-1" title="Special:BookSources/0-521-47730-1"><bdi>0-521-47730-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Molecular+crystals&rft.pages=28&rft.pub=Cambridge+University+Press&rft.date=1995&rft.isbn=0-521-47730-1&rft.au=Wright%2C+John+Dalton&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7sroAgMASIEC%26pg%3DPA28&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-sdbs-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-sdbs_28-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sdbs_28-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">NMR, IR and mass spectra of adamantane can be found in the <a rel="nofollow" class="external text" href="https://sdbs.db.aist.go.jp/sdbs/">SDBS database</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230306094058/https://sdbs.db.aist.go.jp/sdbs/">Archived</a> 2023-03-06 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarch,_J.1987" class="citation book cs1">March, J. (1987). <i>Organic chemistry. Reactions, mechanisms, structure. Advanced course for universities and higher education chemical</i>. Vol. 1. M.: World. p. 137.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+chemistry.+Reactions%2C+mechanisms%2C+structure.+Advanced+course+for+universities+and+higher+education+chemical&rft.place=M.&rft.pages=137&rft.pub=World&rft.date=1987&rft.au=March%2C+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFApplequist,_J.Rivers,_P.Applequist,_D._E.1969" class="citation journal cs1">Applequist, J., Rivers, P., Applequist, D. E. (1969). "Theoretical and experimental studies of optically active bridgehead-substituted adamantanes and related compounds". <i>J. Am. Chem. Soc</i>. <b>91</b> (21): <span class="nowrap">5705–</span>5711. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01049a002">10.1021/ja01049a002</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Theoretical+and+experimental+studies+of+optically+active+bridgehead-substituted+adamantanes+and+related+compounds&rft.volume=91&rft.issue=21&rft.pages=%3Cspan+class%3D%22nowrap%22%3E5705-%3C%2Fspan%3E5711&rft.date=1969&rft_id=info%3Adoi%2F10.1021%2Fja01049a002&rft.au=Applequist%2C+J.&rft.au=Rivers%2C+P.&rft.au=Applequist%2C+D.+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHamill,_H.McKervey,_M._A.1969" class="citation journal cs1">Hamill, H., McKervey, M. A. (1969). "The resolution of 3-methyl-5-bromoadamantanecarboxylic acid". <i>Chem. Comm.</i> (15): 864. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC2969000864a">10.1039/C2969000864a</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Comm.&rft.atitle=The+resolution+of+3-methyl-5-bromoadamantanecarboxylic+acid&rft.issue=15&rft.pages=864&rft.date=1969&rft_id=info%3Adoi%2F10.1039%2FC2969000864a&rft.au=Hamill%2C+H.&rft.au=McKervey%2C+M.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAcarJensenThigpenMcGowen2000" class="citation journal cs1">Acar HY, Jensen JJ, Thigpen K, McGowen JA, Mathias LJ (2000). "Evaluation of the Spacer Effect on Adamantane-Containing Vinyl Polymer <i>T</i> <sub>g</sub>'s". <i>Macromolecules</i>. <b>33</b> (10): <span class="nowrap">3855–</span>3859. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2000MaMol..33.3855A">2000MaMol..33.3855A</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fma991621j">10.1021/ma991621j</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Macromolecules&rft.atitle=Evaluation+of+the+Spacer+Effect+on+Adamantane-Containing+Vinyl+Polymer+T+%3Csub%3Eg%3C%2Fsub%3E%27s&rft.volume=33&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3855-%3C%2Fspan%3E3859&rft.date=2000&rft_id=info%3Adoi%2F10.1021%2Fma991621j&rft_id=info%3Abibcode%2F2000MaMol..33.3855A&rft.aulast=Acar&rft.aufirst=Havva+Yagci&rft.au=Jensen%2C+Jennifer+J.&rft.au=Thigpen%2C+Kevin&rft.au=McGowen%2C+John+A.&rft.au=Mathias%2C+Lon+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMathiasJensenThigpenMcGowen2001" class="citation journal cs1">Mathias LJ, Jensen J, Thigpen K, McGowen J, McCormick D, Somlai L (2001). "Copolymers of 4-adamantylphenyl methacrylate derivatives with methyl methacrylate and styrene". <i>Polymer</i>. <b>42</b> (15): <span class="nowrap">6527–</span>6537. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0032-3861%2801%2900155-0">10.1016/S0032-3861(01)00155-0</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Polymer&rft.atitle=Copolymers+of+4-adamantylphenyl+methacrylate+derivatives+with+methyl+methacrylate+and+styrene&rft.volume=42&rft.issue=15&rft.pages=%3Cspan+class%3D%22nowrap%22%3E6527-%3C%2Fspan%3E6537&rft.date=2001&rft_id=info%3Adoi%2F10.1016%2FS0032-3861%2801%2900155-0&rft.aulast=Mathias&rft.aufirst=Lon+J.&rft.au=Jensen%2C+Jennifer&rft.au=Thigpen%2C+Kevin&rft.au=McGowen%2C+John&rft.au=McCormick%2C+Demetrius&rft.au=Somlai%2C+Louis&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchleyer_P._R.Fort_R._C.Watts_W._E.1964" class="citation journal cs1">Schleyer P. R., Fort R. C., Watts W. E. (1964). "Stable Carbonium Ions. VIII. The 1-Adamantyl Cation". <i>J. Am. Chem. Soc</i>. <b>86</b> (19): <span class="nowrap">4195–</span>4197. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01073a058">10.1021/ja01073a058</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Stable+Carbonium+Ions.+VIII.+The+1-Adamantyl+Cation&rft.volume=86&rft.issue=19&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4195-%3C%2Fspan%3E4197&rft.date=1964&rft_id=info%3Adoi%2F10.1021%2Fja01073a058&rft.au=Schleyer+P.+R.&rft.au=Fort+R.+C.&rft.au=Watts+W.+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOlahPrakashShihKrishnamurthy1985" class="citation journal cs1">Olah GA, Prakash GK, Shih JG, Krishnamurthy VV, Mateescu GD, Liang G, Sipos G, Buss V, Gund TM, Schleyer Pv (1985). "Bridgehead adamantyl, diamantyl, and related cations and dications". <i>J. Am. Chem. 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(2001). <i>Organic Synthesis. Science and art</i>. M.: World. p. 573. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/5-03-003380-7" title="Special:BookSources/5-03-003380-7"><bdi>5-03-003380-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Synthesis.+Science+and+art&rft.place=M.&rft.pages=573&rft.pub=World&rft.date=2001&rft.isbn=5-03-003380-7&rft.au=Smith%2C+W.&rft.au=Bochkov+A.&rft.au=Caple%2C+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBremervon_Ragué_SchleyerSchötzKausch1987" class="citation journal cs1">Bremer M, von Ragué Schleyer P, Schötz K, Kausch M, Schindler M (1987). "Four-Center Two-Electron Bonding in a Tetrahedral Topology. Experimental Realization of Three-Dimensional Homoaromaticity in the 1,3-Dehydro-5,7-adamantanediyl Dication". <i>Angewandte Chemie International Edition in English</i>. <b>26</b> (8): <span class="nowrap">761–</span>763. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.198707611">10.1002/anie.198707611</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition+in+English&rft.atitle=Four-Center+Two-Electron+Bonding+in+a+Tetrahedral+Topology.+Experimental+Realization+of+Three-Dimensional+Homoaromaticity+in+the+1%2C3-Dehydro-5%2C7-adamantanediyl+Dication&rft.volume=26&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E761-%3C%2Fspan%3E763&rft.date=1987&rft_id=info%3Adoi%2F10.1002%2Fanie.198707611&rft.aulast=Bremer&rft.aufirst=Matthias&rft.au=von+Ragu%C3%A9+Schleyer%2C+Paul&rft.au=Sch%C3%B6tz%2C+Karl&rft.au=Kausch%2C+Michael&rft.au=Schindler%2C+Michael&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGelukKeizer1973" class="citation journal cs1">Geluk HW, Keizer VG (1973). "Adamantanone". <i>Organic Syntheses</i>. <b>53</b>: 8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.053.0008">10.15227/orgsyn.053.0008</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Adamantanone&rft.volume=53&rft.pages=8&rft.date=1973&rft_id=info%3Adoi%2F10.15227%2Forgsyn.053.0008&rft.aulast=Geluk&rft.aufirst=H.+W.&rft.au=Keizer%2C+V.+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAdamantane" class="Z3988"></span></span> </li> <li id="cite_note-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-39">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0041">2-Adamantanecarbonitrile</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120710204357/http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0041">Archived</a> 2012-07-10 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> Organic Syntheses, Coll. 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