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id="mw-content-subtitle">(Redirected from <a href="/w/index.php?title=Thiolate&redirect=no" class="mw-redirect" title="Thiolate">Thiolate</a>)</div> </div> <div id="bodyContent" class="content"> <div id="mw-content-text" class="mw-body-content"><script>function mfTempOpenSection(id){var block=document.getElementById("mf-section-"+id);block.className+=" open-block";block.previousSibling.className+=" open-block";}</script><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><section class="mf-section-0" id="mf-section-0"> In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a thiol (<a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˈθaɪɒl/</a>;<a href="#cite_note-1">[1]</a> from <a href="/wiki/Ancient_Greek_language" class="mw-redirect" title="Ancient Greek language">Ancient Greek</a> θεῖον (theion) '<a href="/wiki/Sulfur" title="Sulfur">sulfur</a>'<a href="#cite_note-2">[2]</a>), or thiol derivative, is any <a href="/wiki/Organosulfur_compound" class="mw-redirect" title="Organosulfur compound">organosulfur compound</a> of the form <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style>R−SH, where R represents an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or other organic <a href="/wiki/Substituent" title="Substituent">substituent</a>. The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">−SH <a href="/wiki/Functional_group" title="Functional group">functional group</a> itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> (that is, sulfur takes the place of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> in the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">−OH) group of an alcohol), and the word is a blend of "thio-" with "alcohol". <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Mercapto_Group_General_Formulae.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Mercapto_Group_General_Formulae.png/110px-Mercapto_Group_General_Formulae.png" decoding="async" width="110" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Mercapto_Group_General_Formulae.png/165px-Mercapto_Group_General_Formulae.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/Mercapto_Group_General_Formulae.png/220px-Mercapto_Group_General_Formulae.png 2x" data-file-width="1363" data-file-height="930"></a><figcaption>Thiol with a <style data-mw-deduplicate="TemplateStyles:r981673959">.mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}</style> blue highlighted sulfhydryl group.</figcaption></figure> Many thiols have strong odors resembling that of <a href="/wiki/Garlic" title="Garlic">garlic</a> or rotten eggs. Thiols are used as <a href="/wiki/Odorants" class="mw-redirect" title="Odorants">odorants</a> to assist in the detection of <a href="/wiki/Natural_gas" title="Natural gas">natural gas</a> (which in pure form is odorless), and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans (<a href="/wiki/Help:IPA/English" title="Help:IPA/English">/mərˈkæptæn/</a>)<a href="#cite_note-3">[3]</a> or mercapto compounds,<a href="#cite_note-Patai-4">[4]</a><a href="#cite_note-5">[5]</a><a href="#cite_note-CremlynAn-6">[6]</a> a term introduced in 1832 by <a href="/wiki/William_Christopher_Zeise" title="William Christopher Zeise">William Christopher Zeise</a> and is derived from the <a href="/wiki/Latin" title="Latin">Latin</a> mercurio captāns ('capturing mercury')<a href="#cite_note-ReferenceA-7">[7]</a> because the thiolate group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">RS−) bonds very strongly with <a href="/wiki/Mercury_(element)" title="Mercury (element)">mercury</a> compounds.<a href="#cite_note-8">[8]</a> <div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none"><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><label class="toctogglelabel" for="toctogglecheckbox"></label></div> <ul> <li class="toclevel-1 tocsection-1"><a href="#Structure_and_bonding">1 Structure and bonding</a></li> <li class="toclevel-1 tocsection-2"><a href="#Nomenclature">2 Nomenclature</a></li> <li class="toclevel-1 tocsection-3"><a href="#Physical_properties">3 Physical properties</a> <ul> <li class="toclevel-2 tocsection-4"><a href="#Odor">3.1 Odor</a></li> <li class="toclevel-2 tocsection-5"><a href="#Boiling_points_and_solubility">3.2 Boiling points and solubility</a></li> <li class="toclevel-2 tocsection-6"><a href="#Bonding">3.3 Bonding</a></li> </ul> </li> <li class="toclevel-1 tocsection-7"><a href="#Characterization">4 Characterization</a></li> <li class="toclevel-1 tocsection-8"><a href="#Preparation">5 Preparation</a> <ul> <li class="toclevel-2 tocsection-9"><a href="#Laboratory_methods">5.1 Laboratory methods</a></li> </ul> </li> <li class="toclevel-1 tocsection-10"><a href="#Reactions">6 Reactions</a> <ul> <li class="toclevel-2 tocsection-11"><a href="#S-Alkylation">6.1 S-Alkylation</a></li> <li class="toclevel-2 tocsection-12"><a href="#Acidity">6.2 Acidity</a></li> <li class="toclevel-2 tocsection-13"><a href="#Redox">6.3 Redox</a></li> <li class="toclevel-2 tocsection-14"><a href="#Metal_ion_complexation">6.4 Metal ion complexation</a></li> <li class="toclevel-2 tocsection-15"><a href="#Thioxanthates">6.5 Thioxanthates</a></li> </ul> </li> <li class="toclevel-1 tocsection-16"><a href="#Thiyl_radicals">7 Thiyl radicals</a></li> <li class="toclevel-1 tocsection-17"><a href="#Biological_importance">8 Biological importance</a> <ul> <li class="toclevel-2 tocsection-18"><a href="#Cysteine_and_cystine">8.1 Cysteine and cystine</a></li> <li class="toclevel-2 tocsection-19"><a href="#Cofactors">8.2 Cofactors</a></li> <li class="toclevel-2 tocsection-20"><a href="#In_skunks">8.3 In skunks</a></li> </ul> </li> <li class="toclevel-1 tocsection-21"><a href="#Examples_of_thiols">9 Examples of thiols</a></li> <li class="toclevel-1 tocsection-22"><a href="#See_also">10 See also</a></li> <li class="toclevel-1 tocsection-23"><a href="#References">11 References</a></li> <li class="toclevel-1 tocsection-24"><a href="#External_links">12 External links</a></li> </ul> </div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(1)"><h2 id="Structure_and_bonding">Structure and bonding</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=1" title="Edit section: Structure and bonding" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-1 collapsible-block" id="mf-section-1"> Thiols having the structure R−SH, in which an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> group (R) is attached to a <a href="/wiki/Sulfhydryl" class="mw-redirect" title="Sulfhydryl">sulfhydryl</a> group (SH), are referred to as alkanethiols or alkyl thiols.<a href="#cite_note-9">[9]</a> Thiols and alcohols have similar connectivity. Because sulfur atoms are larger than oxygen atoms, C−S <a href="/wiki/Bond_length" title="Bond length">bond lengths</a> – typically around 180 <a href="/wiki/Picometre" title="Picometre">picometres</a> – are about 40 picometers longer than typical C−O bonds. The C−S−H angles approach 90° whereas the angle for the C−O−H group is more obtuse. In solids and liquids, the <a href="/wiki/Hydrogen-bonding" class="mw-redirect" title="Hydrogen-bonding">hydrogen-bonding</a> between individual thiol groups is weak, the main cohesive force being <a href="/wiki/Van_der_Waals_interaction" class="mw-redirect" title="Van der Waals interaction">Van der Waals interactions</a> between the highly polarizable divalent sulfur centers. The S−H bond is much weaker than the O−H bond as reflected in their respective <a href="/wiki/Bond_dissociation_energy" class="mw-redirect" title="Bond dissociation energy">bond dissociation energies</a> (BDE). For CH3S−H, the BDE is 366 kJ/mol (87 kcal/mol), while for CH3O−H, the BDE is 440 kJ/mol (110 kcal/mol).<a href="#cite_note-10">[10]</a> An S−H bond is moderately <a href="/wiki/Chemical_polarity" title="Chemical polarity">polar</a> because of the small difference in the <a href="/wiki/Electronegativity" title="Electronegativity">electronegativity</a> of sulfur and hydrogen. In contrast, O−H bonds in hydroxyl groups are more polar. Thiols have a lower <a href="/wiki/Bond_dipole_moment" class="mw-redirect" title="Bond dipole moment">dipole moment</a> relative to their corresponding alcohols. </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(2)"><h2 id="Nomenclature">Nomenclature</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=2" title="Edit section: Nomenclature" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-2 collapsible-block" id="mf-section-2"> There are several ways to name the alkylthiols: <ul><li>The suffix -thiol is added to the name of the alkane. This method is nearly identical to <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">naming an alcohol</a> and is used by the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>, e.g. CH3SH would be <a href="/wiki/Methanethiol" title="Methanethiol">methanethiol</a>.</li> <li>The word mercaptan replaces alcohol in the name of the equivalent alcohol compound. Example: CH3SH would be methyl mercaptan, just as CH3OH is called methyl alcohol.</li> <li>The term sulfhydryl- or mercapto- is used as a prefix, e.g. <a href="/wiki/Mercaptopurine" title="Mercaptopurine">mercaptopurine</a>.</li></ul> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(3)"><h2 id="Physical_properties">Physical properties</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=3" title="Edit section: Physical properties" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-3 collapsible-block" id="mf-section-3"> <div class="mw-heading mw-heading3"><h3 id="Odor">Odor</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=4" title="Edit section: Odor" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Many thiols have strong <a href="/wiki/Odor" title="Odor">odors</a> resembling that of <a href="/wiki/Garlic" title="Garlic">garlic</a>. The odors of thiols, particularly those of low molecular weight, are often strong and repulsive. The spray of <a href="/wiki/Skunk" title="Skunk">skunks</a> consists mainly of low-molecular-weight thiols and derivatives.<a href="#cite_note-11">[11]</a><a href="#cite_note-12">[12]</a><a href="#cite_note-13">[13]</a><a href="#cite_note-14">[14]</a><a href="#cite_note-15">[15]</a> These compounds are detectable by the human nose at concentrations of only 10 parts per billion.<a href="#cite_note-16">[16]</a> Human <a href="/wiki/Sweat" class="mw-redirect" title="Sweat">sweat</a> contains (R)/(S)-3-methyl-3-mercapto-1-ol (MSH), detectable at 2 parts per billion and having a fruity, <a href="/wiki/Onion" title="Onion">onion</a>-like odor. (Methylthio)methanethiol (MeSCH2SH; MTMT) is a strong-smelling volatile thiol, also detectable at parts per billion levels, found in male <a href="/wiki/Mouse" title="Mouse">mouse</a> urine. <a href="/wiki/Lawrence_C._Katz" class="mw-redirect" title="Lawrence C. Katz">Lawrence C. Katz</a> and co-workers showed that MTMT functioned as a <a href="/wiki/Semiochemical" title="Semiochemical">semiochemical</a>, activating certain mouse olfactory sensory neurons, and attracting female <a href="/wiki/Mouse" title="Mouse">mice</a>.<a href="#cite_note-17">[17]</a> <a href="/wiki/Copper" title="Copper">Copper</a> has been shown to be required by a specific mouse olfactory receptor, MOR244-3, which is highly responsive to MTMT as well as to various other thiols and related compounds.<a href="#cite_note-18">[18]</a> A human olfactory receptor, <a href="/wiki/OR2T11" title="OR2T11">OR2T11</a>, has been identified which, in the presence of copper, is highly responsive to the gas odorants (see below) <a href="/wiki/Ethanethiol" title="Ethanethiol">ethanethiol</a> and <a href="/wiki/Tert-Butylthiol" title="Tert-Butylthiol">t-butyl mercaptan</a> as well as other low molecular weight thiols, including <a href="/wiki/Allyl_mercaptan" title="Allyl mercaptan">allyl mercaptan</a> found in human <a href="/wiki/Garlic" title="Garlic">garlic</a> breath, and the strong-smelling cyclic sulfide <a href="/wiki/Thietane" title="Thietane">thietane</a>.<a href="#cite_note-19">[19]</a> Thiols are also responsible for a class of <a href="/wiki/Wine_fault" title="Wine fault">wine faults</a> caused by an unintended reaction between sulfur and <a href="/wiki/Yeast_(wine)" class="mw-redirect" title="Yeast (wine)">yeast</a> and the "skunky" odor of beer that has been exposed to ultraviolet light. Not all thiols have unpleasant odors. For example, <a href="/wiki/Furan-2-ylmethanethiol" title="Furan-2-ylmethanethiol">furan-2-ylmethanethiol</a> contributes to the aroma of roasted <a href="/wiki/Coffee" title="Coffee">coffee</a>, whereas <a href="/wiki/Grapefruit_mercaptan" title="Grapefruit mercaptan">grapefruit mercaptan</a>, a <a href="/wiki/Terpene" title="Terpene">monoterpenoid</a> thiol, is responsible for the characteristic scent of <a href="/wiki/Grapefruit" title="Grapefruit">grapefruit</a>. The effect of the latter compound is present only at low concentrations. The pure mercaptan has an unpleasant odor. In the United States, <a href="/wiki/Natural_gas" title="Natural gas">natural gas</a> distributors were required to add thiols, originally <a href="/wiki/Ethanethiol" title="Ethanethiol">ethanethiol</a>, to <a href="/wiki/Natural_gas" title="Natural gas">natural gas</a> (which is naturally odorless) after the deadly <a href="/wiki/New_London_School_explosion" title="New London School explosion">New London School explosion</a> in <a href="/wiki/New_London,_Texas" title="New London, Texas">New London, Texas</a>, in 1937. Many gas distributors were odorizing gas prior to this event. Most currently-used gas odorants contain mixtures of mercaptans and sulfides, with <a href="/wiki/Tert-Butylthiol" title="Tert-Butylthiol">t-butyl mercaptan</a> as the main odor constituent in natural gas and <a href="/wiki/Ethanethiol" title="Ethanethiol">ethanethiol</a> in <a href="/wiki/Liquefied_petroleum_gas" title="Liquefied petroleum gas">liquefied petroleum gas</a> (LPG, propane).<a href="#cite_note-Roberts-20">[20]</a> In situations where thiols are used in commercial industry, such as liquid petroleum gas tankers and bulk handling systems, an oxidizing <a href="/wiki/Catalysis" title="Catalysis">catalyst</a> is used to destroy the odor. A copper-based oxidation catalyst neutralizes the volatile thiols and transforms them into inert products. <div class="mw-heading mw-heading3"><h3 id="Boiling_points_and_solubility">Boiling points and solubility</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=5" title="Edit section: Boiling points and solubility" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Thiols show little association by <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonding</a>, both with water molecules and among themselves. Hence, they have lower <a href="/wiki/Boiling_point" title="Boiling point">boiling points</a> and are less <a href="/wiki/Soluble" class="mw-redirect" title="Soluble">soluble</a> in water and other <a href="/wiki/Solvent#Polarity,_solubility,_and_miscibility" title="Solvent">polar solvents</a> than alcohols of similar molecular weight. For this reason also, thiols and their corresponding sulfide functional group <a href="/wiki/Structural_isomer" title="Structural isomer">isomers</a> have similar solubility characteristics and boiling points, whereas the same is not true of alcohols and their corresponding isomeric ethers. <div class="mw-heading mw-heading3"><h3 id="Bonding">Bonding</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=6" title="Edit section: Bonding" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> The S−H bond in thiols is weak compared to the O−H bond in alcohols. For CH3X−H, the bond enthalpies are 365.07±2.1 kcal/mol for X = S and 440.2±3.0 kcal/mol for X = O.<a href="#cite_note-21">[21]</a> Hydrogen-atom abstraction from a thiol gives a <a href="/wiki/Thiyl_radical" title="Thiyl radical">thiyl radical</a> with the formula RS•, where R = alkyl or aryl. </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(4)"><h2 id="Characterization">Characterization</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=7" title="Edit section: Characterization" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-4 collapsible-block" id="mf-section-4"> Volatile thiols are easily and almost unerringly detected by their distinctive odor. Sulfur-specific analyzers for <a href="/wiki/Gas_chromatograph" class="mw-redirect" title="Gas chromatograph">gas chromatographs</a> are useful. Spectroscopic indicators are the <a href="/wiki/Heavy_water" title="Heavy water">D2O</a>-exchangeable SH signal in the <a href="/wiki/Proton_NMR" class="mw-redirect" title="Proton NMR">1H NMR spectrum</a> (<a href="/wiki/Sulfur-33" class="mw-redirect" title="Sulfur-33">33S</a> is <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a>-active but signals for divalent sulfur are very broad and of little utility<a href="#cite_note-22">[22]</a>). The νSH band appears near 2400 cm−1 in the <a href="/wiki/IR_spectrum" class="mw-redirect" title="IR spectrum">IR spectrum</a>.<a href="#cite_note-Patai-4">[4]</a> In the <a href="/wiki/Nitroprusside_reaction" class="mw-redirect" title="Nitroprusside reaction">nitroprusside reaction</a>, free thiol groups react with <a href="/wiki/Sodium_nitroprusside" title="Sodium nitroprusside">sodium nitroprusside</a> and <a href="/wiki/Ammonium_hydroxide" class="mw-redirect" title="Ammonium hydroxide">ammonium hydroxide</a> to give a red colour. </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(5)"><h2 id="Preparation">Preparation</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=8" title="Edit section: Preparation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-5 collapsible-block" id="mf-section-5"> In industry, methanethiol is prepared by the reaction of <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a> with <a href="/wiki/Methanol" title="Methanol">methanol</a>. This method is employed for the industrial synthesis of <a href="/wiki/Methanethiol" title="Methanethiol">methanethiol</a>: <dl><dd>CH3OH + H2S → CH3SH + H2O</dd></dl> Such reactions are conducted in the presence of acidic catalysts. The other principal route to thiols involves the addition of hydrogen sulfide to <a href="/wiki/Alkene" title="Alkene">alkenes</a>. Such reactions are usually conducted in the presence of an acid catalyst or UV light. <a href="/wiki/Halogen" title="Halogen">Halide</a> displacement, using the suitable organic halide and sodium hydrogen sulfide has also been used.<a href="#cite_note-23">[23]</a> Another method entails the alkylation of <a href="/wiki/Sodium_hydrosulfide" title="Sodium hydrosulfide">sodium hydrosulfide</a>. <dl><dd>RX + NaSH → RSH + NaX (X = Cl, Br, I)</dd></dl> This method is used for the production of <a href="/wiki/Thioglycolic_acid" title="Thioglycolic acid">thioglycolic acid</a> from <a href="/wiki/Chloroacetic_acid" title="Chloroacetic acid">chloroacetic acid</a>. <div class="mw-heading mw-heading3"><h3 id="Laboratory_methods">Laboratory methods</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=9" title="Edit section: Laboratory methods" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> In general, on the typical laboratory scale, the direct reaction of a <a href="/wiki/Halogenoalkane" class="mw-redirect" title="Halogenoalkane">haloalkane</a> with sodium hydrosulfide is inefficient owing to the competing formation of sulfides. Instead, alkyl halides are converted to thiols via an S-alkylation of <a href="/wiki/Thiourea" title="Thiourea">thiourea</a>. This multistep, one-pot process proceeds via the intermediacy of the <a href="/wiki/Isothiouronium_salt" class="mw-redirect" title="Isothiouronium salt">isothiouronium salt</a>, which is hydrolyzed in a separate step:<a href="#cite_note-24">[24]</a><a href="#cite_note-25">[25]</a> <dl><dd>CH3CH2Br + SC(NH2)2 → [CH3CH2SC(NH2)2]Br</dd> <dd>[CH3CH2SC(NH2)2]Br + NaOH → CH3CH2SH + OC(NH2)2 + NaBr</dd></dl> The thiourea route works well with primary halides, especially activated ones. Secondary and tertiary thiols are less easily prepared. Secondary thiols can be prepared from the ketone via the corresponding <a href="/wiki/Thioketal" title="Thioketal">dithioketals</a>.<a href="#cite_note-26">[26]</a> A related two-step process involves alkylation of thiosulfate to give the thiosulfonate ("<a href="/wiki/Bunte_salt" title="Bunte salt">Bunte salt</a>"), followed by hydrolysis. The method is illustrated by one synthesis of <a href="/wiki/Thioglycolic_acid" title="Thioglycolic acid">thioglycolic acid</a>: <dl><dd>ClCH2CO2H + Na2S2O3 → Na[O3S2CH2CO2H] + NaCl</dd></dl> <dl><dd>Na[O3S2CH2CO2H] + H2O → HSCH2CO2H + NaHSO4</dd></dl> <a href="/wiki/Organolithium_compound" class="mw-redirect" title="Organolithium compound">Organolithium compounds</a> and <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a> react with sulfur to give the thiolates, which are readily hydrolyzed:<a href="#cite_note-27">[27]</a> <dl><dd>RLi + S → RSLi</dd> <dd>RSLi + HCl → RSH + LiCl</dd></dl> Phenols can be converted to the thiophenols via rearrangement of their O-aryl dialkylthiocarbamates.<a href="#cite_note-28">[28]</a> Thiols are prepared by reductive dealkylation of sulfides, especially benzyl derivatives and thioacetals.<a href="#cite_note-29">[29]</a> Thiophenols are produced by S-arylation or the replacement of diazonium leaving group with sulfhydryl anion (SH−):<a href="#cite_note-30">[30]</a><a href="#cite_note-31">[31]</a> <dl><dd>ArN+ 2 + SH− → ArSH + N2</dd></dl> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(6)"><h2 id="Reactions">Reactions</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=10" title="Edit section: Reactions" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-6 collapsible-block" id="mf-section-6"> Akin to the chemistry of alcohols, thiols form <a href="/wiki/Sulfide" title="Sulfide">sulfides</a>, <a href="/wiki/Thioacetal" title="Thioacetal">thioacetals</a>, and <a href="/wiki/Thioester" title="Thioester">thioesters</a>, which are analogous to <a href="/wiki/Ethers" class="mw-redirect" title="Ethers">ethers</a>, <a href="/wiki/Acetal" title="Acetal">acetals</a>, and <a href="/wiki/Esters" class="mw-redirect" title="Esters">esters</a> respectively. Thiols and alcohols are also very different in their reactivity, thiols being more easily oxidized than alcohols. Thiolates are more potent nucleophiles than the corresponding <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a>. <div class="mw-heading mw-heading3"><h3 id="S-Alkylation">S-Alkylation</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=11" title="Edit section: S-Alkylation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Thiols, or more specific their conjugate bases, are readily alkylated to give sulfides: <dl><dd>RSH + R′Br + B → RSR′ + [HB]Br (B = base)</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Acidity">Acidity</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=12" title="Edit section: Acidity" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Thiols are easily deprotonated.<a href="#cite_note-32">[32]</a> Relative to the alcohols, thiols are more acidic. The conjugate base of a thiol is called a thiolate. Butanethiol has a <a href="/wiki/PKa" class="mw-redirect" title="PKa">pKa</a> of 10.5 vs 15 for butanol. Thiophenol has a <a href="/wiki/PKa" class="mw-redirect" title="PKa">pKa</a> of 6, versus 10 for <a href="/wiki/Phenol" title="Phenol">phenol</a>. A highly acidic thiol is <a href="/wiki/Pentafluorothiophenol" title="Pentafluorothiophenol">pentafluorothiophenol</a> (C6F5SH) with a pKa of 2.68. Thus, thiolates can be obtained from thiols by treatment with alkali metal hydroxides. <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Thiophenolat_Synthesis.png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Thiophenolat_Synthesis.png/400px-Thiophenolat_Synthesis.png" decoding="async" width="400" height="89" class="mw-file-element" data-file-width="1919" data-file-height="425"></noscript><span class="lazy-image-placeholder" style="width: 400px;height: 89px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Thiophenolat_Synthesis.png/400px-Thiophenolat_Synthesis.png" data-width="400" data-height="89" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Thiophenolat_Synthesis.png/600px-Thiophenolat_Synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Thiophenolat_Synthesis.png/800px-Thiophenolat_Synthesis.png 2x" data-class="mw-file-element"> </a><figcaption>Synthesis of thiophenolate from thiophenol</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Redox">Redox</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=13" title="Edit section: Redox" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Thiols, especially in the presence of base, are readily <a href="/wiki/Redox" title="Redox">oxidized</a> by reagents such as <a href="/wiki/Bromine" title="Bromine">bromine</a> and <a href="/wiki/Iodine" title="Iodine">iodine</a> to give an organic <a href="/wiki/Disulfide" title="Disulfide">disulfide</a> (R−S−S−R). <dl><dd>2 R−SH + Br2 → R−S−S−R + 2 HBr</dd></dl> Oxidation by more powerful reagents such as <a href="/wiki/Sodium_hypochlorite" title="Sodium hypochlorite">sodium hypochlorite</a> or <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> can also yield <a href="/wiki/Sulfonic_acid" title="Sulfonic acid">sulfonic acids</a> (RSO3H). <dl><dd>R−SH + 3 H2O2 → RSO3H + 3 H2O</dd></dl> Oxidation can also be effected by oxygen in the presence of catalysts:<a href="#cite_note-33">[33]</a> <dl><dd>2 R–SH + <style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style>1⁄2 O2 → RS−SR + H2O</dd></dl> Thiols participate in thiol-disulfide exchange: <dl><dd>RS−SR + 2 R′SH → 2 RSH + R′S−SR′</dd></dl> This reaction is important in nature. <div class="mw-heading mw-heading3"><h3 id="Metal_ion_complexation">Metal ion complexation</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=14" title="Edit section: Metal ion complexation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> With metal ions, thiolates behave as ligands to form <a href="/wiki/Transition_metal_thiolate_complex" title="Transition metal thiolate complex">transition metal thiolate complexes</a>. The term mercaptan is derived from the <a href="/wiki/Latin" title="Latin">Latin</a> mercurium captans (capturing mercury)<a href="#cite_note-ReferenceA-7">[7]</a> because the thiolate group bonds so strongly with <a href="/wiki/Mercury_(element)" title="Mercury (element)">mercury</a> compounds. According to <a href="/wiki/HSAB_theory" title="HSAB theory">hard/soft acid/base (HSAB) theory</a>, sulfur is a relatively soft (polarizable) atom. This explains the tendency of thiols to bind to soft elements and ions such as mercury, lead, or cadmium. The stability of metal thiolates parallels that of the corresponding sulfide minerals. <div class="mw-heading mw-heading3"><h3 id="Thioxanthates">Thioxanthates</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=15" title="Edit section: Thioxanthates" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Thiolates react with <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">carbon disulfide</a> to give <a href="/wiki/Thioxanthate" title="Thioxanthate">thioxanthate</a> (RSCS− 2). </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(7)"><h2 id="Thiyl_radicals">Thiyl radicals</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=16" title="Edit section: Thiyl radicals" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-7 collapsible-block" id="mf-section-7"> <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">Main article: <a href="/wiki/Thiyl_radical" title="Thiyl radical">Thiyl radical</a></div><a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">Free radicals</a> derived from mercaptans, called <a href="/wiki/Thiyl_radical" title="Thiyl radical">thiyl radicals</a>, are commonly invoked to explain reactions in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a> and <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>. They have the formula RS• where R is an organic substituent such as <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>.<a href="#cite_note-CremlynAn-6">[6]</a> They arise from or can be generated by a number of routes, but the principal method is H-atom abstraction from thiols. Another method involves <a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">homolysis</a> of organic disulfides.<a href="#cite_note-Ullmann-34">[34]</a> In biology thiyl radicals are responsible for the formation of the deoxyribonucleic acids, building blocks for <a href="/wiki/DNA" title="DNA">DNA</a>. This conversion is catalysed by <a href="/wiki/Ribonucleotide_reductase" title="Ribonucleotide reductase">ribonucleotide reductase</a> (see figure).<a href="#cite_note-35">[35]</a> Thiyl intermediates also are produced by the oxidation of <a href="/wiki/Glutathione" title="Glutathione">glutathione</a>, an antioxidant in biology. Thiyl radicals (sulfur-centred) can transform to carbon-centred radicals via <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom exchange <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibria</a>. The formation of <a href="/wiki/Carbon" title="Carbon">carbon</a>-centred radicals could lead to protein damage via the formation of <a href="/wiki/Carbon" title="Carbon">C</a>−C bonds or backbone fragmentation.<a href="#cite_note-Hofstetter-36">[36]</a> Because of the weakness of the S−H bond, thiols can function as <a href="/wiki/Scavenger_(chemistry)" title="Scavenger (chemistry)">scavengers</a> of <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a>.<a href="#cite_note-Koch_Parliament_Brown_Urtasun_2010_pp._55%E2%80%9368-37">[37]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(8)"><h2 id="Biological_importance">Biological importance</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=17" title="Edit section: Biological importance" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-8 collapsible-block" id="mf-section-8"> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:RNR_reaction.png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/RNR_reaction.png/400px-RNR_reaction.png" decoding="async" width="400" height="349" class="mw-file-element" data-file-width="505" data-file-height="441"></noscript><span class="lazy-image-placeholder" style="width: 400px;height: 349px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/RNR_reaction.png/400px-RNR_reaction.png" data-width="400" data-height="349" data-srcset="//upload.wikimedia.org/wikipedia/commons/2/2c/RNR_reaction.png 1.5x" data-class="mw-file-element"> </a><figcaption>The catalytic cycle for <a href="/wiki/Ribonucleotide_reductase" title="Ribonucleotide reductase">ribonucleotide reductase</a>, demonstrating the role of thiyl radicals in producing the genetic machinery of life.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Cysteine_and_cystine">Cysteine and cystine</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=18" title="Edit section: Cysteine and cystine" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> As the functional group of the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Cysteine" title="Cysteine">cysteine</a>, the thiol group plays a very important role in biology. When the thiol groups of two cysteine residues (as in monomers or constituent units) are brought near each other in the course of <a href="/wiki/Protein" title="Protein">protein</a> folding, an <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation reaction</a> can generate a <a href="/wiki/Cystine" title="Cystine">cystine</a> unit with a <a href="/wiki/Disulfide_bond" class="mw-redirect" title="Disulfide bond">disulfide bond</a> (−S−S−). Disulfide bonds can contribute to a protein's <a href="/wiki/Tertiary_structure" class="mw-redirect" title="Tertiary structure">tertiary structure</a> if the cysteines are part of the same <a href="/wiki/Peptide" title="Peptide">peptide</a> chain, or contribute to the <a href="/wiki/Quaternary_structure" class="mw-redirect" title="Quaternary structure">quaternary structure</a> of multi-unit proteins by forming fairly strong covalent bonds between different peptide chains. A physical manifestation of cysteine-cystine equilibrium is provided by <a href="/wiki/Hair_straightening" title="Hair straightening">hair straightening</a> technologies.<a href="#cite_note-38">[38]</a> Sulfhydryl groups in the <a href="/wiki/Active_site" title="Active site">active site</a> of an <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> can form <a href="/wiki/Noncovalent_bond" class="mw-redirect" title="Noncovalent bond">noncovalent bonds</a> with the enzyme's <a href="/wiki/Substrate_(biochemistry)" class="mw-redirect" title="Substrate (biochemistry)">substrate</a> as well, contributing to covalent <a href="/wiki/Catalysis" title="Catalysis">catalytic activity</a> in <a href="/wiki/Catalytic_triad" title="Catalytic triad">catalytic triads</a>. Active site cysteine residues are the functional unit in <a href="/wiki/Cysteine_protease" title="Cysteine protease">cysteine protease</a> <a href="/wiki/Catalytic_triad" title="Catalytic triad">catalytic triads</a>. Cysteine residues may also react with heavy metal ions (Zn2+, Cd2+, Pb2+, Hg2+, Ag+) because of the high affinity between the soft sulfide and the soft metal (see <a href="/wiki/Hard_and_soft_acids_and_bases" class="mw-redirect" title="Hard and soft acids and bases">hard and soft acids and bases</a>). This can deform and inactivate the protein, and is one mechanism of <a href="/wiki/Heavy_metal_poisoning" class="mw-redirect" title="Heavy metal poisoning">heavy metal poisoning</a>. Drugs containing thiol group <a href="/wiki/6-Mercaptopurine" class="mw-redirect" title="6-Mercaptopurine">6-Mercaptopurine</a> (anticancer) <a href="/wiki/Captopril" title="Captopril">Captopril</a> (antihypertensive) <a href="/wiki/D-penicillamine" class="mw-redirect" title="D-penicillamine">D-penicillamine</a> (antiarthritic) <a href="/w/index.php?title=Sodium_aurothiolate&action=edit&redlink=1" class="new" title="Sodium aurothiolate (page does not exist)">Sodium aurothiolate</a> (antiarthritic)<a href="#cite_note-39">[39]</a> <div class="mw-heading mw-heading3"><h3 id="Cofactors">Cofactors</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=19" title="Edit section: Cofactors" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Many <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactors</a> (non-protein-based helper molecules) feature thiols. The biosynthesis and degradation of fatty acids and related long-chain hydrocarbons is conducted on a scaffold that anchors the growing chain through a thioester derived from the thiol <a href="/wiki/Coenzyme_A" title="Coenzyme A">Coenzyme A</a>. The <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of <a href="/wiki/Methane" title="Methane">methane</a>, the principal <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> on Earth, arises from the reaction mediated by <a href="/wiki/Coenzyme_M" title="Coenzyme M">coenzyme M</a>, 2-mercaptoethyl sulfonic acid. Thiolates, the conjugate bases derived from thiols, form strong complexes with many metal ions, especially those classified as soft. The stability of metal thiolates parallels that of the corresponding sulfide minerals. <div class="mw-heading mw-heading3"><h3 id="In_skunks">In skunks</h3> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=20" title="Edit section: In skunks" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> The defensive spray of <a href="/wiki/Skunks" class="mw-redirect" title="Skunks">skunks</a> consists mainly of low-molecular-weight thiols and derivatives with a foul odor, which protects the skunk from predators. Owls are able to prey on skunks, as they lack a sense of smell.<a href="#cite_note-40">[40]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(9)"><h2 id="Examples_of_thiols">Examples of thiols</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=21" title="Edit section: Examples of thiols" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-9 collapsible-block" id="mf-section-9"> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 20em;"> <ul><li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a> – CH3SH [methyl mercaptan]</li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a> – C2H5SH [ethyl mercaptan]</li> <li><a href="/wiki/Propanethiol" title="Propanethiol">1-Propanethiol</a> – C3H7SH [n-propyl mercaptan]</li> <li><a href="/wiki/2-Propanethiol" class="mw-redirect" title="2-Propanethiol">2-Propanethiol</a> – CH3CH(SH)CH3 [2C3 mercaptan]</li> <li><a href="/wiki/Allyl_mercaptan" title="Allyl mercaptan">Allyl mercaptan</a> – CH2=CHCH2SH [2-propenethiol]</li> <li><a href="/wiki/Butanethiol" class="mw-redirect" title="Butanethiol">Butanethiol</a> – C4H9SH [n-butyl mercaptan]</li> <li><a href="/wiki/Tert-Butyl_mercaptan" class="mw-redirect" title="Tert-Butyl mercaptan">tert-Butyl mercaptan</a> – (CH3)3CSH [t-butyl mercaptan]</li> <li><a href="/w/index.php?title=Pentanethiols&action=edit&redlink=1" class="new" title="Pentanethiols (page does not exist)">Pentanethiols</a> – C5H11SH [pentyl mercaptan]</li> <li><a href="/wiki/Thiophenol" title="Thiophenol">Thiophenol</a> – C6H5SH</li> <li><a href="/wiki/Dimercaptosuccinic_acid" class="mw-redirect" title="Dimercaptosuccinic acid">Dimercaptosuccinic acid</a></li> <li><a href="/wiki/Thioacetic_acid" title="Thioacetic acid">Thioacetic acid</a></li> <li><a href="/wiki/Coenzyme_A" title="Coenzyme A">Coenzyme A</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Metallothionein" title="Metallothionein">Metallothionein</a></li> <li><a href="/wiki/Cysteine" title="Cysteine">Cysteine</a></li> <li><a href="/wiki/2-Mercaptoethanol" title="2-Mercaptoethanol">2-Mercaptoethanol</a></li> <li><a href="/wiki/Dithiothreitol" title="Dithiothreitol">Dithiothreitol</a>/<a href="/wiki/Dithioerythritol" title="Dithioerythritol">dithioerythritol</a> (an <a href="/wiki/Epimer" title="Epimer">epimeric</a> pair)</li> <li><a href="/wiki/2-Mercaptoindole" class="mw-redirect" title="2-Mercaptoindole">2-Mercaptoindole</a></li> <li><a href="/wiki/Grapefruit_mercaptan" title="Grapefruit mercaptan">Grapefruit mercaptan</a></li> <li><a href="/wiki/Furan-2-ylmethanethiol" title="Furan-2-ylmethanethiol">Furan-2-ylmethanethiol</a></li> <li><a href="/wiki/3-Mercaptopropane-1,2-diol" title="3-Mercaptopropane-1,2-diol">3-Mercaptopropane-1,2-diol</a></li> <li><a href="/wiki/3-Mercapto-1-propanesulfonic_acid" title="3-Mercapto-1-propanesulfonic acid">3-Mercapto-1-propanesulfonic acid</a></li> <li><a href="/wiki/1-Hexadecanethiol" class="mw-redirect" title="1-Hexadecanethiol">1-Hexadecanethiol</a></li> <li><a href="/wiki/Pentachlorobenzenethiol" title="Pentachlorobenzenethiol">Pentachlorobenzenethiol</a></li></ul> </div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(10)"><h2 id="See_also">See also</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=22" title="Edit section: See also" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-10 collapsible-block" id="mf-section-10"> <ul><li><a href="/wiki/Doctor_sweetening_process" title="Doctor sweetening process">Doctor sweetening process</a></li> <li><a href="/wiki/Odorizer" title="Odorizer">Odorizer</a></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Saville_reaction" title="Saville reaction">Saville reaction</a></li> <li><a href="/wiki/Thiol-disulfide_exchange" class="mw-redirect" title="Thiol-disulfide exchange">Thiol-disulfide exchange</a></li></ul> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(11)"><h2 id="References">References</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=23" title="Edit section: References" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-11 collapsible-block" id="mf-section-11"> <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-1"><a href="#cite_ref-1">^</a> <a href="/wiki/Dictionary.com" title="Dictionary.com">Dictionary Reference</a>: <a rel="nofollow" class="external text" href="http://dictionary.reference.com/browse/thiol">thiol</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130411021707/http://dictionary.reference.com/browse/thiol">Archived</a> 2013-04-11 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> </li> <li id="cite_note-2"><a href="#cite_ref-2">^</a> <a rel="nofollow" class="external text" href="https://www.perseus.tufts.edu/hopper/text?doc=Perseus%3Atext%3A1999.04.0057%3Aentry%3Dqei%3Don1">θεῖον</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170510073237/http://www.perseus.tufts.edu/hopper/text?doc=Perseus%3Atext%3A1999.04.0057%3Aentry%3Dqei%3Don1">Archived</a> 2017-05-10 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, Henry George Liddell, Robert Scott, A Greek–English Lexicon </li> <li id="cite_note-3"><a href="#cite_ref-3">^</a> <a href="/wiki/Dictionary.com" title="Dictionary.com">Dictionary Reference</a>: <a rel="nofollow" class="external text" href="http://dictionary.reference.com/browse/mercaptan">mercaptan</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20121113062439/http://dictionary.reference.com/browse/mercaptan">Archived</a> 2012-11-13 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> </li> <li id="cite_note-Patai-4">^ <a href="#cite_ref-Patai_4-0">a</a> <a href="#cite_ref-Patai_4-1">b</a> <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 id="CITEREFPatai,_Saul1974" class="citation book cs1">Patai, Saul, ed. (1974). The Chemistry of the Thiol Group. Part 1. London: Wiley. <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%2F9780470771310">10.1002/9780470771310</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771310" title="Special:BookSources/9780470771310"><bdi>9780470771310</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Chemistry+of+the+Thiol+Group.+Part+1&rft.place=London&rft.pub=Wiley&rft.date=1974&rft_id=info%3Adoi%2F10.1002%2F9780470771310&rft.isbn=9780470771310&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"> </li> <li id="cite_note-5"><a href="#cite_ref-5">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPatai,_Saul1974" class="citation book cs1">Patai, Saul, ed. (1974). The Chemistry of the Thiol Group. Part 2. London: Wiley. <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%2F9780470771327">10.1002/9780470771327</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771327" title="Special:BookSources/9780470771327"><bdi>9780470771327</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Chemistry+of+the+Thiol+Group.+Part+2&rft.place=London&rft.pub=Wiley&rft.date=1974&rft_id=info%3Adoi%2F10.1002%2F9780470771327&rft.isbn=9780470771327&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"> </li> <li id="cite_note-CremlynAn-6">^ <a href="#cite_ref-CremlynAn_6-0">a</a> <a href="#cite_ref-CremlynAn_6-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFR._J._Cremlyn1996" class="citation book cs1">R. J. Cremlyn (1996). An Introduction to Organosulfur Chemistry. Chichester: John Wiley and Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-95512-2" title="Special:BookSources/978-0-471-95512-2"><bdi>978-0-471-95512-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=An+Introduction+to+Organosulfur+Chemistry&rft.place=Chichester&rft.pub=John+Wiley+and+Sons&rft.date=1996&rft.isbn=978-0-471-95512-2&rft.au=R.+J.+Cremlyn&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"> </li> <li id="cite_note-ReferenceA-7">^ <a href="#cite_ref-ReferenceA_7-0">a</a> <a href="#cite_ref-ReferenceA_7-1">b</a> Oxford American Dictionaries (<a href="/wiki/Mac_OS_X_Leopard" title="Mac OS X Leopard">Mac OS X Leopard</a>). </li> <li id="cite_note-8"><a href="#cite_ref-8">^</a> See: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZeise1834" class="citation journal cs1 cs1-prop-foreign-lang-source">Zeise, William Christopher (1834). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=umn.31951d00004546r&view=1up&seq=131">"Mercaptanet, med bemaerkninger over nogle andre nye producter af svovelvinsyresaltene, som og af den tunge vinolie, ved sulfureter"</a> [Mercaptan, with remarks on some other new products of salts of ethyl hydrogen sulfate as well as of heavy oil of wine, by means of hydrogen sulfide]. Kongelige Danske Videnskabers Selskabs Skrifter. 4th series (in Danish). 6: 1–70.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Kongelige+Danske+Videnskabers+Selskabs+Skrifter&rft.atitle=Mercaptanet%2C+med+bemaerkninger+over+nogle+andre+nye+producter+af+svovelvinsyresaltene%2C+som+og+af+den+tunge+vinolie%2C+ved+sulfureter&rft.volume=6&rft.pages=1-70&rft.date=1834&rft.aulast=Zeise&rft.aufirst=William+Christopher&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dumn.31951d00004546r%26view%3D1up%26seq%3D131&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"> On p. 13 the word "mercaptan" is coined.</li> <li>German translation: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZeise1834" class="citation journal cs1 cs1-prop-foreign-lang-source">Zeise, W. C. (1834). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=wu.89048351654&view=1up&seq=383">"Das Mercaptan, nebst Bermerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl"</a> [Mercaptan together with comments on some new products from the effect of hydrogen sulfide on salts of ethyl sulfate ((C2H5)HSO4) and heavy oil of wine (a mixture of diethyl sulfate, diethyl sulfite, and polymerized ethylene)]. Annalen der Physik und Chemie. 2nd series (in German). 31 (24): 369–431.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Physik+und+Chemie&rft.atitle=Das+Mercaptan%2C+nebst+Bermerkungen+%C3%BCber+einige+neue+Producte+aus+der+Einwirkung+der+Sulfurete+auf+weinschwefelsaure+Salze+und+auf+das+Wein%C3%B6l&rft.volume=31&rft.issue=24&rft.pages=369-431&rft.date=1834&rft.aulast=Zeise&rft.aufirst=W.+C.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dwu.89048351654%26view%3D1up%26seq%3D383&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"> From p. 378: " … nenne ich den vom Quecksilber aufgenommenen Stoff Mercaptum (von: Corpus mercurio captum) … " ( … I name the substance [that is] absorbed by mercury "mercaptum" (from: the body (substance) [that] has been absorbed by mercury) … )</li> <li>German translation is reprinted in:<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZeise1834" class="citation journal cs1">Zeise, W. C. (1834). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=uiug.30112063582438;view=1up;seq=267">"Das Mercaptan, nebst Bemerkungen über einige andere neue Erzeugnisse der Wirkung schwefelweinsaurer Salze, wie auch des schweren Weinöls auf Sulphurete"</a>. Journal für Praktische Chemie. 1 (1): 257–268, 345–356, 396–413, 457–475. <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%2Fprac.18340010154">10.1002/prac.18340010154</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+Praktische+Chemie&rft.atitle=Das+Mercaptan%2C+nebst+Bemerkungen+%C3%BCber+einige+andere+neue+Erzeugnisse+der+Wirkung+schwefelweinsaurer+Salze%2C+wie+auch+des+schweren+Wein%C3%B6ls+auf+Sulphurete&rft.volume=1&rft.issue=1&rft.pages=257-268%2C+345-356%2C+396-413%2C+457-475&rft.date=1834&rft_id=info%3Adoi%2F10.1002%2Fprac.18340010154&rft.aulast=Zeise&rft.aufirst=W.+C.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Duiug.30112063582438%3Bview%3D1up%3Bseq%3D267&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"></li> <li>Summarized in: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZeise1834" class="citation journal cs1">Zeise, W. C. (1834). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dmgTAAAAQAAJ&pg=PA1">"Ueber das Mercaptan"</a> [On mercaptan]. Annalen der Pharmacie. 11 (1): 1–10. <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%2Fjlac.18340110102">10.1002/jlac.18340110102</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150320202059/http://books.google.com/books?id=dmgTAAAAQAAJ&pg=PA1">Archived</a> from the original on 2015-03-20.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Pharmacie&rft.atitle=Ueber+das+Mercaptan&rft.volume=11&rft.issue=1&rft.pages=1-10&rft.date=1834&rft_id=info%3Adoi%2F10.1002%2Fjlac.18340110102&rft.aulast=Zeise&rft.aufirst=W.+C.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdmgTAAAAQAAJ%26pg%3DPA1&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZeise1834" class="citation journal cs1">Zeise, William Christopher (1834). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=1Jc5AAAAcAAJ&pg=PA87">"Sur le mercaptan; avec des observations sur d'autres produits resultant de l'action des sulfovinates ainsi que de l'huile de vin, sur des sulfures metalliques"</a> [On mercaptan; with observations on other products resulting from the action of sulfovinates [typically, ethyl hydrogen sulfate] as well as oil of wine [a mixture of diethylsulfate and ethylene polymers] on metal sulfides]. Annales de Chimie et de Physique. 56: 87–97. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150320194543/http://books.google.com/books?id=1Jc5AAAAcAAJ&pg=PA87">Archived</a> from the original on 2015-03-20.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Sur+le+mercaptan%3B+avec+des+observations+sur+d%27autres+produits+resultant+de+l%27action+des+sulfovinates+ainsi+que+de+l%27huile+de+vin%2C+sur+des+sulfures+metalliques&rft.volume=56&rft.pages=87-97&rft.date=1834&rft.aulast=Zeise&rft.aufirst=William+Christopher&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D1Jc5AAAAcAAJ%26pg%3DPA87&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"> "Mercaptan" (ethyl thiol) was discovered in 1834 by the Danish professor of chemistry <a href="/wiki/William_Christopher_Zeise" title="William Christopher Zeise">William Christopher Zeise</a> (1789–1847). He called it "mercaptan", a contraction of "corpus mercurio captans" (mercury-capturing substance) [p. 88], because it reacted violently with mercury(II) oxide ("deutoxide de mercure") [p. 92].</li> <li>The article in Annales de Chimie et de Physique (1834) was translated from the German article: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZeise1834" class="citation journal cs1">Zeise, W. C. (1834). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wCUAAAAAMAAJ&pg=PA369">"Das Mercaptan, nebst Bemerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl"</a>. 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New York: Pearson Benjamin Cummings. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/campbellbiology00reec/page/n112">65</a>, 83.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Campbell+Biology&rft.place=New+York&rft.pages=65%2C+83&rft.edition=Ninth&rft.pub=Pearson+Benjamin+Cummings&rft.date=2011&rft.aulast=Reece&rft.aufirst=Urry&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fcampbellbiology00reec&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"> </li> <li id="cite_note-39"><a href="#cite_ref-39">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMalle2007" class="citation journal cs1">Malle, E (2007). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2078229">"Myeloperoxidase: a target for new drug development?"</a>. 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Retrieved 3 May 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=theowlstrust.org&rft.atitle=Understanding+Owls+%E2%80%93+The+Owls+Trust&rft_id=https%3A%2F%2Ftheowlstrust.org%2Fowl-hub%2Fowl-education-programmes%2Funderstanding-owls%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiol" class="Z3988"> </li> </ol></div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(12)"><h2 id="External_links">External links</h2> <a role="button" href="/w/index.php?title=Thiol&action=edit&section=24" title="Edit section: External links" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-12 collapsible-block" id="mf-section-12"> <ul><li><a rel="nofollow" class="external text" href="http://www.periodicvideos.com/videos/mv_smelly.htm">Mercaptans (or Thiols)</a> at <a href="/wiki/The_Periodic_Table_of_Videos" class="mw-redirect" title="The Periodic Table of Videos">The Periodic Table of Videos</a> (University of Nottingham)</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20061010191459/http://dysa.northwestern.edu/CurrOrgChem.pdf">Applications, Properties, and Synthesis of ω-Functionalized n-Alkanethiols and Disulfides – the Building Blocks of Self-Assembled Monolayers</a> by D. Witt, R. Klajn, P. Barski, B.A. Grzybowski at Northwestern University.</li> <li><a rel="nofollow" class="external text" href="http://www.factmonster.com/ce6/sci/A0832739.html">Mercaptan</a>, by <a href="/wiki/The_Columbia_Electronic_Encyclopedia" class="mw-redirect" title="The Columbia Electronic Encyclopedia">The Columbia Electronic Encyclopedia</a></li> <li><a rel="nofollow" class="external text" href="http://www.columbiagaspamd.com/community_outreach/mercaptan.htm">What is Mercaptan?</a>, by Columbia Gas of Pennsylvania and Maryland.</li> <li><a rel="nofollow" class="external text" href="http://chemistry.about.com/od/chemistryfaqs/f/blsmell.htm">What Is the Worst Smelling Chemical?</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20110606080415/http://chemistry.about.com/od/chemistryfaqs/f/blsmell.htm">Archived</a> 2011-06-06 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, by About Chemistry.</li></ul> <div class="navbox-styles"><style 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class="last-modified-bar" href="/w/index.php?title=Thiol&action=history"> <div class="post-content last-modified-bar__content"> Last edited on 4 July 2024, at 02:58 </div> </a> <div class="post-content footer-content"> <div id='mw-data-after-content'> <div class="read-more-container"></div> </div> <div id="p-lang"> <h4>Languages</h4> <section> <ul id="p-variants" class="minerva-languages"></ul> <ul class="minerva-languages"><li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Merkaptaan" title="Merkaptaan – Afrikaans" lang="af" hreflang="af" data-title="Merkaptaan" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target">Afrikaans</a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AB%D9%8A%D9%88%D9%84" title="ثيول – Arabic" lang="ar" hreflang="ar" data-title="ثيول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Tiol" title="Tiol – Asturian" lang="ast" hreflang="ast" data-title="Tiol" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target">Asturianu</a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Tiollar" title="Tiollar – Azerbaijani" lang="az" hreflang="az" data-title="Tiollar" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Tiol" title="Tiol – Bosnian" lang="bs" hreflang="bs" data-title="Tiol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Tiol" title="Tiol – Catalan" lang="ca" hreflang="ca" data-title="Tiol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Thioly" title="Thioly – Czech" lang="cs" hreflang="cs" data-title="Thioly" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Thiol" title="Thiol – Danish" lang="da" hreflang="da" data-title="Thiol" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Thiole" title="Thiole – German" lang="de" hreflang="de" data-title="Thiole" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Tioolid" title="Tioolid – Estonian" lang="et" hreflang="et" data-title="Tioolid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%98%CE%B5%CE%B9%CF%8C%CE%BB%CE%B5%CF%82" title="Θειόλες – Greek" lang="el" hreflang="el" data-title="Θειόλες" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Tiol" title="Tiol – Spanish" lang="es" hreflang="es" data-title="Tiol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Tioloj" title="Tioloj – Esperanto" lang="eo" hreflang="eo" data-title="Tioloj" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Merkaptano" title="Merkaptano – Basque" lang="eu" hreflang="eu" data-title="Merkaptano" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%DB%8C%D9%88%D9%84_(%D8%B4%DB%8C%D9%85%DB%8C)" title="تیول (شیمی) – Persian" lang="fa" hreflang="fa" data-title="تیول (شیمی)" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Thiol" title="Thiol – French" lang="fr" hreflang="fr" data-title="Thiol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Tiol" title="Tiol – Galician" lang="gl" hreflang="gl" data-title="Tiol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%8B%B8%EC%9D%B4%EC%98%AC" title="싸이올 – Korean" lang="ko" hreflang="ko" data-title="싸이올" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B9%D5%AB%D5%B8%D5%AC%D5%B6%D5%A5%D6%80" title="Թիոլներ – Armenian" lang="hy" hreflang="hy" data-title="Թիոլներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Tioli" title="Tioli – Croatian" lang="hr" hreflang="hr" data-title="Tioli" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Tiol" title="Tiol – Indonesian" lang="id" hreflang="id" data-title="Tiol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Tioli" title="Tioli – Italian" lang="it" hreflang="it" data-title="Tioli" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%AA%D7%99%D7%95%D7%9C" title="תיול – Hebrew" lang="he" hreflang="he" data-title="תיול" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9B%E1%83%94%E1%83%A0%E1%83%99%E1%83%90%E1%83%9E%E1%83%A2%E1%83%90%E1%83%9C%E1%83%94%E1%83%91%E1%83%98" title="მერკაპტანები – Georgian" lang="ka" hreflang="ka" data-title="მერკაპტანები" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target">ქართული</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9C%D0%B5%D1%80%D0%BA%D0%B0%D0%BF%D1%82%D0%B0%D0%BD%D0%B4%D0%B0%D1%80" title="Меркаптандар – Kazakh" lang="kk" hreflang="kk" data-title="Меркаптандар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9C%D0%B5%D1%80%D0%BA%D0%B0%D0%BF%D1%82%D0%B0%D0%BD%D0%B4%D0%B0%D1%80" title="Меркаптандар – Kyrgyz" lang="ky" hreflang="ky" data-title="Меркаптандар" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target">Кыргызча</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Tiolis" title="Tiolis – Lithuanian" lang="lt" hreflang="lt" data-title="Tiolis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Tiolok" title="Tiolok – Hungarian" lang="hu" hreflang="hu" data-title="Tiolok" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A2%D0%B8%D0%BE%D0%BB" title="Тиол – Macedonian" lang="mk" hreflang="mk" data-title="Тиол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Tiol" title="Tiol – Malay" lang="ms" hreflang="ms" data-title="Tiol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Thiol" title="Thiol – Dutch" lang="nl" hreflang="nl" data-title="Thiol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%81%E3%82%AA%E3%83%BC%E3%83%AB" title="チオール – Japanese" lang="ja" hreflang="ja" data-title="チオール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Tiol" title="Tiol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Tiol" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Tiol" title="Tiol – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Tiol" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target">Norsk nynorsk</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Ti%C3%B2l" title="Tiòl – Occitan" lang="oc" hreflang="oc" data-title="Tiòl" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Merkaptanlar" title="Merkaptanlar – Uzbek" lang="uz" hreflang="uz" data-title="Merkaptanlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target">Oʻzbekcha / ўзбекча</a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%A5%E0%A8%BE%E0%A8%87%E0%A8%93%E0%A8%B2" title="ਥਾਇਓਲ – Punjabi" lang="pa" hreflang="pa" data-title="ਥਾਇਓਲ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target">ਪੰਜਾਬੀ</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tiole" title="Tiole – Polish" lang="pl" hreflang="pl" data-title="Tiole" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Tiol" title="Tiol – Portuguese" lang="pt" hreflang="pt" data-title="Tiol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Tiol" title="Tiol – Romanian" lang="ro" hreflang="ro" data-title="Tiol" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B8%D0%BE%D0%BB%D1%8B" title="Тиолы – Russian" lang="ru" hreflang="ru" data-title="Тиолы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Thiol" title="Thiol – Simple English" lang="en-simple" hreflang="en-simple" data-title="Thiol" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Tiol" title="Tiol – Slovak" lang="sk" hreflang="sk" data-title="Tiol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Tiol" title="Tiol – Slovenian" lang="sl" hreflang="sl" data-title="Tiol" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Tiol" title="Tiol – Serbian" lang="sr" hreflang="sr" data-title="Tiol" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Tiol" title="Tiol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Tiol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Tiolit" title="Tiolit – Finnish" lang="fi" hreflang="fi" data-title="Tiolit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Tiol" title="Tiol – Swedish" lang="sv" hreflang="sv" data-title="Tiol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%A4%E0%AE%AF%E0%AF%8B%E0%AE%B2%E0%AF%8D" title="தயோல் – Tamil" lang="ta" hreflang="ta" data-title="தயோல்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target">தமிழ்</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Tiyol" title="Tiyol – Turkish" lang="tr" hreflang="tr" data-title="Tiyol" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A2%D1%96%D0%BE%D0%BB%D0%B8" title="Тіоли – Ukrainian" lang="uk" hreflang="uk" data-title="Тіоли" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Thiol" title="Thiol – Vietnamese" lang="vi" hreflang="vi" data-title="Thiol" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%A1%AB%E9%86%87" title="硫醇 – Cantonese" lang="yue" hreflang="yue" data-title="硫醇" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target">粵語</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A1%AB%E9%86%87" title="硫醇 – Chinese" lang="zh" hreflang="zh" data-title="硫醇" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li></ul> </section> </div> <div class="minerva-footer-logo"><img src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" alt="Wikipedia" width="120" height="18" style="width: 7.5em; height: 1.125em;"/> </div> <ul id="footer-info" class="footer-info hlist hlist-separated"> <li id="footer-info-lastmod"> This page was last edited on 4 July 2024, at 02:58 (UTC).</li> <li id="footer-info-copyright">Content is available under <a class="external" rel="nofollow" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">CC BY-SA 4.0</a> unless otherwise noted.</li> </ul> <ul id="footer-places" class="footer-places hlist hlist-separated"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a 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