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11.25H12H14C14.4142 11.25 14.75 11.5857 14.75 12C14.75 12.4142 14.4142 12.75 14 12.75H12H10C9.58579 12.75 9.25 12.4142 9.25 12ZM9.25 17C9.25 16.5857 9.58579 16.25 10 16.25H12H14C14.4142 16.25 14.75 16.5857 14.75 17C14.75 17.4142 14.4142 17.75 14 17.75H12H10C9.58579 17.75 9.25 17.4142 9.25 17Z" fill="currentColor"/> </svg> </span><span class="bre-article-menu__list-item-text tw-hidden md:max-lg:tw-inline">Аннотация</span></a><span style="display:none;" class=""><span>Аннотация</span></span></span><a href="/c/izomeriia-27922f/annotation" class="bre-article-menu__list-item tw-mx-auto tw-flex lg:tw-hidden"><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-gray-1"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"> <path fill-rule="evenodd" clip-rule="evenodd" d="M18.2363 4.12686C18.2363 3.43651 18.796 2.87686 19.4863 2.87686C20.1767 2.87686 20.7363 3.43651 20.7363 4.12686C20.7363 4.81722 20.1767 5.37686 19.4863 5.37686C18.796 5.37686 18.2363 4.81722 18.2363 4.12686ZM19.4863 1.37686C17.9675 1.37686 16.7363 2.60808 16.7363 4.12686C16.7363 4.43206 16.786 4.72564 16.8778 4.99996H7C4.79086 4.99996 3 6.79082 3 8.99996V19C3 21.2091 4.79086 23 7 23H17C19.2091 23 21 21.2091 21 19V8.99996C21 8.16642 20.745 7.39244 20.3089 6.75173C21.4258 6.40207 22.2363 5.35911 22.2363 4.12686C22.2363 2.60808 21.0051 1.37686 19.4863 1.37686ZM7 6.49996H16.6319L14.6964 8.43547C14.4035 8.72837 14.4035 9.20324 14.6964 9.49613C14.9893 9.78903 15.4641 9.78903 15.757 9.49613L18.3547 6.89846C19.0438 7.34362 19.5 8.11852 19.5 8.99996V19C19.5 20.3807 18.3807 21.5 17 21.5H7C5.61929 21.5 4.5 20.3807 4.5 19V8.99996C4.5 7.61924 5.61929 6.49996 7 6.49996ZM9.25 12C9.25 11.5857 9.58579 11.25 10 11.25H12H14C14.4142 11.25 14.75 11.5857 14.75 12C14.75 12.4142 14.4142 12.75 14 12.75H12H10C9.58579 12.75 9.25 12.4142 9.25 12ZM9.25 17C9.25 16.5857 9.58579 16.25 10 16.25H12H14C14.4142 16.25 14.75 16.5857 14.75 17C14.75 17.4142 14.4142 17.75 14 17.75H12H10C9.58579 17.75 9.25 17.4142 9.25 17Z" fill="currentColor"/> </svg> </span><span class="bre-article-menu__list-item-text tw-hidden md:max-lg:tw-inline">Аннотация</span></a></div><div class="tw-grow tw-basis-0 max-md:tw-max-w-[80px]"><span data-v-tippy class="tw-mx-auto tw-hidden lg:tw-flex"><a href="/c/izomeriia-27922f/media" class="bre-article-menu__list-item"><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-gray-1"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"> <path fill-rule="evenodd" clip-rule="evenodd" d="M17 4H7C5.61929 4 4.5 5.11929 4.5 6.5V17.5C4.5 18.1033 4.71367 18.6566 5.06946 19.0885L15.6829 8.95748C15.8374 8.81003 16.0474 8.73542 16.2603 8.75237C16.4732 8.76931 16.6687 8.87621 16.7979 9.04625L19.5 12.6023V6.5C19.5 5.11929 18.3807 4 17 4ZM19.5 15.0592C19.465 15.0278 19.4324 14.9926 19.4028 14.9538L16.1114 10.6221L6.37067 19.9201C6.57173 19.9723 6.78263 20 7 20H17C18.3807 20 19.5 18.8807 19.5 17.5V15.0592ZM7 2.5C4.79086 2.5 3 4.29086 3 6.5V17.5C3 19.7091 4.79086 21.5 7 21.5H17C19.2091 21.5 21 19.7091 21 17.5V6.5C21 4.29086 19.2091 2.5 17 2.5H7ZM9.20078 7.25C8.51042 7.25 7.95078 7.80964 7.95078 8.5C7.95078 9.19036 8.51042 9.75 9.20078 9.75C9.89113 9.75 10.4508 9.19036 10.4508 8.5C10.4508 7.80964 9.89113 7.25 9.20078 7.25ZM6.45078 8.5C6.45078 6.98122 7.68199 5.75 9.20078 5.75C10.7196 5.75 11.9508 6.98122 11.9508 8.5C11.9508 10.0188 10.7196 11.25 9.20078 11.25C7.68199 11.25 6.45078 10.0188 6.45078 8.5Z" fill="currentColor"/> </svg> </span><span class="bre-article-menu__list-item-text tw-hidden md:max-lg:tw-inline">Медиа</span></a><span style="display:none;" class=""><span>Медиа</span></span></span><a href="/c/izomeriia-27922f/media" class="bre-article-menu__list-item tw-mx-auto tw-flex lg:tw-hidden"><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-gray-1"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"> <path fill-rule="evenodd" clip-rule="evenodd" d="M17 4H7C5.61929 4 4.5 5.11929 4.5 6.5V17.5C4.5 18.1033 4.71367 18.6566 5.06946 19.0885L15.6829 8.95748C15.8374 8.81003 16.0474 8.73542 16.2603 8.75237C16.4732 8.76931 16.6687 8.87621 16.7979 9.04625L19.5 12.6023V6.5C19.5 5.11929 18.3807 4 17 4ZM19.5 15.0592C19.465 15.0278 19.4324 14.9926 19.4028 14.9538L16.1114 10.6221L6.37067 19.9201C6.57173 19.9723 6.78263 20 7 20H17C18.3807 20 19.5 18.8807 19.5 17.5V15.0592ZM7 2.5C4.79086 2.5 3 4.29086 3 6.5V17.5C3 19.7091 4.79086 21.5 7 21.5H17C19.2091 21.5 21 19.7091 21 17.5V6.5C21 4.29086 19.2091 2.5 17 2.5H7ZM9.20078 7.25C8.51042 7.25 7.95078 7.80964 7.95078 8.5C7.95078 9.19036 8.51042 9.75 9.20078 9.75C9.89113 9.75 10.4508 9.19036 10.4508 8.5C10.4508 7.80964 9.89113 7.25 9.20078 7.25ZM6.45078 8.5C6.45078 6.98122 7.68199 5.75 9.20078 5.75C10.7196 5.75 11.9508 6.98122 11.9508 8.5C11.9508 10.0188 10.7196 11.25 9.20078 11.25C7.68199 11.25 6.45078 10.0188 6.45078 8.5Z" fill="currentColor"/> </svg> </span><span class="bre-article-menu__list-item-text tw-hidden md:max-lg:tw-inline">Медиа</span></a></div><div class="tw-grow tw-basis-0 max-md:tw-max-w-[80px]"><span data-v-tippy class="tw-mx-auto tw-hidden lg:tw-flex"><a href="/c/izomeriia-27922f/references" class="bre-article-menu__list-item"><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-gray-1"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"> <path fill-rule="evenodd" clip-rule="evenodd" d="M5 3.25C3.48122 3.25 2.25 4.48122 2.25 6V16.1667C2.25 17.6854 3.48122 18.9167 5 18.9167H9.3C9.80519 18.9167 10.2974 19.1269 10.6662 19.5139C11.0362 19.9022 11.25 20.4361 11.25 21C11.25 21.4142 11.5858 21.75 12 21.75C12.4142 21.75 12.75 21.4142 12.75 21C12.75 20.4227 12.9564 19.8833 13.3026 19.4973C13.6464 19.114 14.0941 18.9167 14.5412 18.9167H19C20.5188 18.9167 21.75 17.6855 21.75 16.1667V6C21.75 4.48122 20.5188 3.25 19 3.25H15.3882C14.2627 3.25 13.2022 3.74922 12.4341 4.60572C12.266 4.79308 12.1147 4.99431 11.9809 5.20674C11.8358 4.98777 11.6713 4.78092 11.4885 4.58908C10.6758 3.73626 9.56568 3.25 8.4 3.25H5ZM12.75 17.993C13.2735 17.6237 13.8929 17.4167 14.5412 17.4167H19C19.6904 17.4167 20.25 16.857 20.25 16.1667V6C20.25 5.30964 19.6904 4.75 19 4.75H15.3882C14.7165 4.75 14.0534 5.04681 13.5507 5.60725C13.0457 6.17037 12.75 6.95001 12.75 7.77778V17.993ZM11.25 18.0438V7.77778C11.25 6.96341 10.9414 6.18924 10.4026 5.62389C9.86506 5.05976 9.14388 4.75 8.4 4.75H5C4.30964 4.75 3.75 5.30964 3.75 6V16.1667C3.75 16.857 4.30964 17.4167 5 17.4167H9.3C10.0044 17.4167 10.6825 17.64 11.25 18.0438Z" fill="currentColor"/> </svg> </span><span class="bre-article-menu__list-item-text tw-hidden md:max-lg:tw-inline">Библиография</span></a><span style="display:none;" class=""><span>Библиография</span></span></span><a href="/c/izomeriia-27922f/references" class="bre-article-menu__list-item tw-mx-auto tw-flex lg:tw-hidden"><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-gray-1"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"> <path fill-rule="evenodd" clip-rule="evenodd" d="M5 3.25C3.48122 3.25 2.25 4.48122 2.25 6V16.1667C2.25 17.6854 3.48122 18.9167 5 18.9167H9.3C9.80519 18.9167 10.2974 19.1269 10.6662 19.5139C11.0362 19.9022 11.25 20.4361 11.25 21C11.25 21.4142 11.5858 21.75 12 21.75C12.4142 21.75 12.75 21.4142 12.75 21C12.75 20.4227 12.9564 19.8833 13.3026 19.4973C13.6464 19.114 14.0941 18.9167 14.5412 18.9167H19C20.5188 18.9167 21.75 17.6855 21.75 16.1667V6C21.75 4.48122 20.5188 3.25 19 3.25H15.3882C14.2627 3.25 13.2022 3.74922 12.4341 4.60572C12.266 4.79308 12.1147 4.99431 11.9809 5.20674C11.8358 4.98777 11.6713 4.78092 11.4885 4.58908C10.6758 3.73626 9.56568 3.25 8.4 3.25H5ZM12.75 17.993C13.2735 17.6237 13.8929 17.4167 14.5412 17.4167H19C19.6904 17.4167 20.25 16.857 20.25 16.1667V6C20.25 5.30964 19.6904 4.75 19 4.75H15.3882C14.7165 4.75 14.0534 5.04681 13.5507 5.60725C13.0457 6.17037 12.75 6.95001 12.75 7.77778V17.993ZM11.25 18.0438V7.77778C11.25 6.96341 10.9414 6.18924 10.4026 5.62389C9.86506 5.05976 9.14388 4.75 8.4 4.75H5C4.30964 4.75 3.75 5.30964 3.75 6V16.1667C3.75 16.857 4.30964 17.4167 5 17.4167H9.3C10.0044 17.4167 10.6825 17.64 11.25 18.0438Z" fill="currentColor"/> </svg> </span><span class="bre-article-menu__list-item-text tw-hidden md:max-lg:tw-inline">Библиография</span></a></div><div class="tw-grow tw-basis-0 max-md:tw-max-w-[80px]"><span data-v-tippy class="tw-mx-auto tw-hidden lg:tw-flex"><a href="/c/izomeriia-27922f/versions" class="bre-article-menu__list-item"><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-gray-1"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"> <path fill-rule="evenodd" clip-rule="evenodd" d="M10.9565 3.85864H7.51619C7.8045 3.2057 8.4577 2.75 9.21734 2.75H13.5652H14.7687C15.4365 2.75 16.0697 3.0466 16.4972 3.55959L19.2502 6.86313C19.5871 7.26748 19.7717 7.77718 19.7717 8.30354V10.6957V16.7826C19.7717 17.5422 19.316 18.1954 18.663 18.4838V13.3043V10.9122C18.663 10.0349 18.3555 9.18542 17.7939 8.51149L15.0409 5.20795C14.3284 4.35298 13.273 3.85864 12.1601 3.85864H10.9565ZM14.913 22.7499C16.6051 22.7499 18.0354 21.6293 18.5022 20.0898C20.0762 19.8113 21.2717 18.4365 21.2717 16.7826V10.6957V8.30354C21.2717 7.42628 20.9641 6.57678 20.4025 5.90285L17.6496 2.59931C16.9371 1.74434 15.8817 1.25 14.7687 1.25H13.5652H9.21734C7.56341 1.25 6.18869 2.44548 5.91016 4.01947C4.37062 4.48633 3.25 5.91662 3.25 7.60864V18.9999C3.25 21.071 4.92893 22.7499 7 22.7499H14.913ZM7 5.35864C5.75736 5.35864 4.75 6.366 4.75 7.60864V18.9999C4.75 20.2426 5.75736 21.2499 7 21.2499H14.913C16.1557 21.2499 17.163 20.2426 17.163 18.9999V13.3043V10.9122C17.163 10.7991 17.1545 10.6867 17.1378 10.5761H15.3043C13.9296 10.5761 12.8152 9.46164 12.8152 8.08694V5.45611C12.6051 5.39215 12.3845 5.35864 12.1601 5.35864H10.9565H7ZM14.3152 6.68014V8.08694C14.3152 8.63322 14.758 9.07607 15.3043 9.07607H16.3118L14.3152 6.68014ZM6.72827 13.3043C6.72827 12.8901 7.06406 12.5543 7.47827 12.5543H14.4348C14.849 12.5543 15.1848 12.8901 15.1848 13.3043C15.1848 13.7185 14.849 14.0543 14.4348 14.0543H7.47827C7.06406 14.0543 6.72827 13.7185 6.72827 13.3043ZM7.47827 16.9022C7.06406 16.9022 6.72827 17.238 6.72827 17.6522C6.72827 18.0664 7.06406 18.4022 7.47827 18.4022H10.9565C11.3707 18.4022 11.7065 18.0664 11.7065 17.6522C11.7065 17.238 11.3707 16.9022 10.9565 16.9022H7.47827Z" fill="currentColor"/> </svg> </span><span class="bre-article-menu__list-item-text tw-hidden md:max-lg:tw-inline">Версии</span></a><span style="display:none;" class=""><span>Версии</span></span></span><a href="/c/izomeriia-27922f/versions" class="bre-article-menu__list-item tw-mx-auto tw-flex lg:tw-hidden"><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-gray-1"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"> <path fill-rule="evenodd" clip-rule="evenodd" d="M10.9565 3.85864H7.51619C7.8045 3.2057 8.4577 2.75 9.21734 2.75H13.5652H14.7687C15.4365 2.75 16.0697 3.0466 16.4972 3.55959L19.2502 6.86313C19.5871 7.26748 19.7717 7.77718 19.7717 8.30354V10.6957V16.7826C19.7717 17.5422 19.316 18.1954 18.663 18.4838V13.3043V10.9122C18.663 10.0349 18.3555 9.18542 17.7939 8.51149L15.0409 5.20795C14.3284 4.35298 13.273 3.85864 12.1601 3.85864H10.9565ZM14.913 22.7499C16.6051 22.7499 18.0354 21.6293 18.5022 20.0898C20.0762 19.8113 21.2717 18.4365 21.2717 16.7826V10.6957V8.30354C21.2717 7.42628 20.9641 6.57678 20.4025 5.90285L17.6496 2.59931C16.9371 1.74434 15.8817 1.25 14.7687 1.25H13.5652H9.21734C7.56341 1.25 6.18869 2.44548 5.91016 4.01947C4.37062 4.48633 3.25 5.91662 3.25 7.60864V18.9999C3.25 21.071 4.92893 22.7499 7 22.7499H14.913ZM7 5.35864C5.75736 5.35864 4.75 6.366 4.75 7.60864V18.9999C4.75 20.2426 5.75736 21.2499 7 21.2499H14.913C16.1557 21.2499 17.163 20.2426 17.163 18.9999V13.3043V10.9122C17.163 10.7991 17.1545 10.6867 17.1378 10.5761H15.3043C13.9296 10.5761 12.8152 9.46164 12.8152 8.08694V5.45611C12.6051 5.39215 12.3845 5.35864 12.1601 5.35864H10.9565H7ZM14.3152 6.68014V8.08694C14.3152 8.63322 14.758 9.07607 15.3043 9.07607H16.3118L14.3152 6.68014ZM6.72827 13.3043C6.72827 12.8901 7.06406 12.5543 7.47827 12.5543H14.4348C14.849 12.5543 15.1848 12.8901 15.1848 13.3043C15.1848 13.7185 14.849 14.0543 14.4348 14.0543H7.47827C7.06406 14.0543 6.72827 13.7185 6.72827 13.3043ZM7.47827 16.9022C7.06406 16.9022 6.72827 17.238 6.72827 17.6522C6.72827 18.0664 7.06406 18.4022 7.47827 18.4022H10.9565C11.3707 18.4022 11.7065 18.0664 11.7065 17.6522C11.7065 17.238 11.3707 16.9022 10.9565 16.9022H7.47827Z" fill="currentColor"/> </svg> </span><span class="bre-article-menu__list-item-text tw-hidden md:max-lg:tw-inline">Версии</span></a></div></div></div></nav><div><meta itemprop="image primaryImageOfPage" content="https://i.bigenc.ru/resizer/resize?sign=_oZGNMT12w20jVMCGLd7_Q&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=120"><article itemscope itemprop="mainEntity" itemtype="https://schema.org/Article"><div itemprop="publisher" itemscope itemtype="https://schema.org/Organization"><meta itemprop="name" content="Автономная некоммерческая организация «Национальный научно-образовательный центр «Большая российская энциклопедия»"><meta itemprop="address" content="Покровский бульвар, д. 8, стр. 1А, Москва, 109028"><meta itemprop="telephone" content="+7 (495) 781-15-95"><meta itemprop="logo" content="https://s.bigenc.ru/_nuxt/logo.98u7ubS9.svg"></div><div itemprop="copyrightHolder" itemscope itemtype="https://schema.org/Organization"><meta itemprop="name" content="Автономная некоммерческая организация «Национальный научно-образовательный центр «Большая российская энциклопедия»"><meta itemprop="address" content="Покровский бульвар, д. 8, стр. 1А, Москва, 109028"><meta itemprop="telephone" content="+7 (495) 781-15-95"><meta itemprop="logo" content="https://s.bigenc.ru/_nuxt/logo.98u7ubS9.svg"></div><meta itemprop="articleSection" content="Термины"><meta itemprop="headline" content="Изомерия"><meta itemprop="keywords" content="Научные термины в органической химии, Научные термины в неорганической химии, Химические законы, Химические теории"><div class="bre-article-page max-md:tw-mt-10 md:max-lg:tw-mt-[81px] max-md:tw-mt-[105px]"><nav class="bre-article-loc -hide-on-desktop-s"><div class="bre-article-loc-button"><span class="bre-article-loc-title">Содержание</span><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-primary-black"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"><path d="M6 9l6 6 6-6" stroke="currentColor" stroke-width="1.5" stroke-linecap="round"/></svg> </span><div class="bre-article-loc-short">Историческая справка</div></div></nav><div class="article-sidebar -hide-on-desktop-s"><div class="article-sidebar-button -show-on-tablet -hide-on-desktop-s"><span class="article-sidebar-title">Информация</span><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-primary-black"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"><path d="M6 9l6 6 6-6" stroke="currentColor" stroke-width="1.5" stroke-linecap="round"/></svg> </span><div class="article-sidebar-text -show-on-tablet -hide-on-desktop-s">Изомерия</div></div><div class="article-sidebar-wrapper -hide-on-tablet"><header class="bre-article-header -hide-on-tablet"><div class="bre-label__wrap"><span data-v-tippy class="tw-leading-[0px]"><a href="/t/terms" class="bre-label _link">Термины</a><span style="display:none;" class=""><span>Термины</span></span></span></div><h1 class="bre-article-header-title">Изомерия</h1></header><section class="-hide-on-tablet tw-h-14 md:tw-h-20"><div><div><div itemprop="interactionStatistic" itemscope itemtype="https://schema.org/InteractionCounter"><meta itemprop="interactionType" content="https://schema.org/ViewAction"><meta itemprop="userInteractionCount" content=""></div><div itemprop="interactionStatistic" itemscope itemtype="https://schema.org/InteractionCounter"><meta itemprop="interactionType" content="https://schema.org/ShareAction"><meta itemprop="userInteractionCount" content=""></div><div itemprop="interactionStatistic" itemscope itemtype="https://schema.org/InteractionCounter"><meta itemprop="interactionType" content="https://schema.org/LikeAction"><meta itemprop="userInteractionCount" content=""></div></div><span></span></div></section><span class="bre-media-image article-sidebar-image _note-exclude _clean" data-width="100%" data-display="block"><span class="bre-media-figure _note-exclude _clean" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container _placeholder"><meta itemprop="name" content="Химия"><meta itemprop="caption" content="Химия. Научно-образовательный портал «Большая российская энциклопедия»"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=_oZGNMT12w20jVMCGLd7_Q&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Химия" data-nuxt-img sizes="320px" srcset="https://i.bigenc.ru/resizer/resize?sign=_oZGNMT12w20jVMCGLd7_Q&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=Mj7syzY4qsowwDnbvl7INQ&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=WBHjuP_BJC6NzjbzS170zA&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=E2zfLZmy9Ma2FS3Az9fIbQ&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=ds7dpUugUbRfiPjQK9-nfw&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=-BIt-K0CauiCHnEQiykBBQ&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=57YV3LcckQbWzGa4yj4hIA&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=1mJ4dHRO7wNCrvaAwb3lOw&filename=vault/168d4a6ed5bb2642309d953f369e1da6.webp&width=1920 1920w" title="Химия" class="" itemprop="contentUrl"></span></span></span></span><div class="article-sidebar-meta"><dl class="tw-mt-0"><dt>Области знаний:</dt><dd>Стереохимия</dd></dl></div></div></div><div class="bre-article-page__container"><div class="bre-article-page__content bre-article-content"><header class="bre-article-header -show-on-tablet"><div class="bre-label__wrap"><span data-v-tippy class="tw-leading-[0px]"><a href="/t/terms" class="bre-label _link">Термины</a><span style="display:none;" class=""><span>Термины</span></span></span></div><h1 class="bre-article-header-title">Изомерия</h1></header><section class="tw-flex"><div class="-show-on-tablet tw-h-14 md:tw-h-20"></div><span></span></section><div class="js-preview-link-root"><div itemprop="articleBody" class="bre-article-body"><section><section><p><b>Изомери́я</b> (от <a href="/c/izo-chast-slozhnykh-slov-3b73bc" class="bre-preview-link" itemprop="url" data-external="false">изо…</a> и греч. μέρος – доля, часть), явление, заключающееся в существовании <a href="/c/khimicheskie-soedineniia-601cba" class="bre-preview-link" itemprop="url" data-external="false">химических соединений</a>, одинаковых по <a href="/c/khimicheskie-formuly-8f11b0" class="bre-preview-link" itemprop="url" data-external="false">составу</a>, с одинаковой <a href="/c/molekuliarnaia-massa-4b35de" class="bre-preview-link" itemprop="url" data-external="false">молекулярной массой</a>, но различающихся по структуре. Такие соединения называются изомерами. Изомеры могут превращаться друг в друга в результате реакций <a href="/c/izomerizatsiia-6039fe" class="bre-preview-link" itemprop="url" data-external="false">изомеризации</a>. Структурные различия обусловливают различное взаимное влияние <a href="/c/atom-8fe711" class="bre-preview-link" itemprop="url" data-external="false">атомов</a> в <a href="/c/molekula-de7079" class="bre-preview-link" itemprop="url" data-external="false">молекулах</a> и предопределяют разные физические и химические свойства изомеров. Изомерия чрезвычайно распространена в <a href="/c/organicheskaia-khimiia-b9437f" class="bre-preview-link" itemprop="url" data-external="false">органической химии</a> и является одной из основных причин разнообразия и многочисленности органических соединений. В <a href="/c/neorganicheskaia-khimiia-70dd52" class="bre-preview-link" itemprop="url" data-external="false">неорганической химии</a> изомерия встречается в основном для <a href="/c/kompleksnye-soedineniia-3addaf" class="bre-preview-link" itemprop="url" data-external="false">комплексных соединений</a>.</p><h2 id="h2_istoricheskaya_spravka">Историческая справка</h2><p><span class="bre-media-image _note-exclude" data-width="25%" data-display="left"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Уно Троили. Портрет Йёнса Якоба Берцелиуса. По картине Улофа Юхана Сёдермарка"><meta itemprop="caption" content="Уно Троили. Портрет Йёнса Якоба Берцелиуса. 1843. По картине Улофа Юхана Сёдермарка. Национальный музей Швеции, Стокгольм."><meta itemprop="copyrightNotice" content="Nationalmuseum"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=NqtR58xglIsnNx8cRron4Q&filename=vault/cd38cfce3f117522927e3ee685b03ee0.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Уно Троили. Портрет Йёнса Якоба Берцелиуса. По картине Улофа Юхана Сёдермарка" data-nuxt-img sizes="320px" srcset="https://i.bigenc.ru/resizer/resize?sign=NqtR58xglIsnNx8cRron4Q&filename=vault/cd38cfce3f117522927e3ee685b03ee0.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=sUw5wQ1OrLRalfGR-qJQmQ&filename=vault/cd38cfce3f117522927e3ee685b03ee0.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=J3wZooNj47H0VqLLFKyB4Q&filename=vault/cd38cfce3f117522927e3ee685b03ee0.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=NcPyV5PxlbSa48EiUCY4RA&filename=vault/cd38cfce3f117522927e3ee685b03ee0.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=OPHaXV-c63zbwNljUKfpPg&filename=vault/cd38cfce3f117522927e3ee685b03ee0.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=KRWk_BveEfUkjOjuCO2xvg&filename=vault/cd38cfce3f117522927e3ee685b03ee0.webp&width=1024 1024w" title="Уно Троили. Портрет Йёнса Якоба Берцелиуса. По картине Улофа Юхана Сёдермарка" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Уно Троили. Портрет Йёнса Якоба Берцелиуса. 1843. По картине Улофа Юхана Сёдермарка. Национальный музей Швеции, Стокгольм.</span><span style="display:none;" class=""><span>Уно Троили. Портрет Йёнса Якоба Берцелиуса. 1843. По картине Улофа Юхана Сёдермарка. Национальный музей Швеции, Стокгольм.</span></span></span></span></span></span></span></span>Термин «изомерия» ввёл <a href="/c/bertselius-iions-iakob-dd657f" class="bre-preview-link" itemprop="url" data-external="false">Й. Я. Берцелиус</a> в 1830 г., завершая полемику между <a href="/c/libikh-iustus-fon-68d404" class="bre-preview-link" itemprop="url" data-external="false">Ю. фон Либихом</a> и <a href="/c/violer-fridrikh-a35015" class="bre-preview-link" itemprop="url" data-external="false">Ф. Вёлером</a> по вопросу существования двух резко отличающихся по свойствам веществ, имеющих один и тот же состав AgCNO, – цианата и фульмината серебра, и опираясь на результаты исследований <a href="/c/vinnye-kisloty-0b9428" class="bre-preview-link" itemprop="url" data-external="false">винной</a> и виноградной кислот. Сущность изомерии была объяснена позднее на основе теории химического строения.</p><h2 id="h2_vidы_izomerii">Виды изомерии</h2><p>Выделяют 2 основных вида изомерии: структурную и пространственную (<a href="/c/stereoizomery-32de69" class="bre-preview-link" itemprop="url" data-external="false">стереоизомерию</a>). Структурные изомеры различаются порядком <a href="/c/khimicheskaia-sviaz-df39ab" class="bre-preview-link" itemprop="url" data-external="false">связей</a> атомов в молекуле, т. е. химическим строением. Стереоизомеры (пространственные изомеры) при одинаковом порядке связей атомов в молекуле различаются взаимным расположением атомов в пространстве.</p><h3 id="h3_strukturnaya_izomeriya">Структурная изомерия</h3><p>Структурная изомерия подразделяется на изомерию <a href="/c/uglerod-dc7cd3" class="bre-preview-link" itemprop="url" data-external="false">углеродного</a> скелета (скелетную изомерию), изомерию положения (позиционную изомерию), метамерию и другие виды.</p><h4 id="h4_izomeriya_uglerodnogo_skeleta">Изомерия углеродного скелета</h4><p>Изомерия углеродного скелета обусловлена различным порядком связей углеродных атомов, образующих скелет молекулы. Для конкретизации структурных особенностей изомеров скелетная изомерия подразделяется на изомерию углеродной цепи, изомерию <a href="/c/tsiklicheskie-soedineniia-1be5db" class="bre-preview-link" itemprop="url" data-external="false">цикла</a> и изомерию боковой цепи. Например, изомерия углеродной цепи характерна для <a href="/c/alkany-960e55" class="bre-preview-link" itemprop="url" data-external="false">алканов</a> начиная с <a href="/c/butany-829c24" class="bre-preview-link" itemprop="url" data-external="false">четвёртого</a> члена гомологического ряда C<sub>4</sub>H<sub>10</sub>, который имеет 2 структурных изомера: <i>н</i>-<a href="/c/butan-khimicheskoe-soedinenie-0b97a7" class="bre-preview-link" itemprop="url" data-external="false">бутан</a> CH<sub>3</sub>−CH<sub>2</sub>−CH<sub>2</sub>−CH<sub>3</sub> и изобутан (2-метилпропан) CH<sub>3</sub>−CH(CH<sub>3</sub>)−CH<sub>3</sub>. Пятый член ряда алканов C<sub>5</sub>H<sub>12 </sub>имеет 3 изомера: CH<sub>3</sub>−CH<sub>2</sub>−CH<sub>2</sub>−CH<sub>2</sub>−CH<sub>3</sub> – <i>н</i>-<a href="/c/pentan-21c0be" class="bre-preview-link" itemprop="url" data-external="false">пентан</a>, CH<sub>3</sub>−CH(CH<sub>3</sub>)−CH<sub>2</sub>−CH<sub>3</sub> – изопентан (2-метилбутан) и неопентан (2,2-диметилпропан) CH<sub>3</sub>−(CH<sub>3</sub>)<sub>2</sub>−CH<sub>3</sub>. С удлинением цепи число возможных изомеров быстро возрастает. Так, для алканов состава C<sub>10</sub>H<sub>22</sub> возможно существование 75 структурных изомеров, для C<sub>13</sub>H<sub>28</sub> – 802 изомеров, для C<sub>20</sub>H<sub>42</sub> – более 366 тыс. изомеров.</p><p>Для <a href="/c/alitsiklicheskie-soedineniia-bd5c22" class="bre-preview-link" itemprop="url" data-external="false">алициклических соединений</a> характерны изомерия цикла и изомерия боковой цепи. Например, среди скелетных изомеров (формулы I–IV) метилциклопентан (I), <a href="/c/tsiklogeksan-c1cfda" class="bre-preview-link" itemprop="url" data-external="false">циклогексан</a> (II) и пропилциклопропан (III) являются циклическими изомерами, а пропилциклопропан (III) и изопропилциклопропан (IV) – изомерами боковой цепи.</p><p><span class="bre-media-image _note-exclude" data-width="75%" data-display="block"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Скелетные изомеры"><meta itemprop="caption" content="Скелетные изомеры."><meta itemprop="copyrightNotice" content="Архив БРЭ"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=uxYQTFGLS3V2oP5JwU4wtw&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Скелетные изомеры" data-nuxt-img sizes="640px" srcset="https://i.bigenc.ru/resizer/resize?sign=uxYQTFGLS3V2oP5JwU4wtw&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=nLIDwsHQjyzWiA2mH_C4_w&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=zmORc6klkrKPQ_2tnJfnWg&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=f5nPxKVy7mBFpDOVHCDThg&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=kLiRr5RxcLOsfwRnEQPVmw&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=z-cSYb1NwDb-FHaiz6U1ig&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=PyPDZDV4jeeu6CxH5vvu6w&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=cRBGp-U5RiHZLMGdsUjHMA&filename=vault/21d598bcc146602829028a793ef8a104.webp&width=1920 1920w" title="Скелетные изомеры" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Скелетные изомеры.</span><span style="display:none;" class=""><span>Скелетные изомеры.</span></span></span></span></span></span></span></span>Различия в свойствах скелетных изомеров проявляются в разнице их <a href="/c/temperatura-kipeniia-fbb237" class="bre-preview-link" itemprop="url" data-external="false">температур кипения</a> (изомеры с нормальной углеродной цепью кипят при более высокой температуре, чем изомеры с разветвлённой цепью), <a href="/c/plotnost-veshchestva-dacc8e" class="bre-preview-link" itemprop="url" data-external="false">плотности</a> и др. <i>н</i>-Алканы, например, в отличие от разветвлённых изомеров, обладают меньшей <a href="/c/detonatsionnaia-stoikost-1bd2f4" class="bre-preview-link" itemprop="url" data-external="false">детонационной стойкостью</a>, образуют комплексы с <a href="/c/mochevina-63b73f" class="bre-preview-link" itemprop="url" data-external="false">мочевиной</a> (<a href="/c/klatraty-782534" class="bre-preview-link" itemprop="url" data-external="false">клатраты</a>).</p><h4 id="h4_izomeriya_polozheniya">Изомерия положения</h4><p>Изомерия положения обусловлена различным положением <a href="/c/funktsional-naia-gruppa-cabb22" class="bre-preview-link" itemprop="url" data-external="false">функциональных групп</a>, заместителей или <a href="/c/kratnye-sviazi-e92881" class="bre-preview-link" itemprop="url" data-external="false">кратных связей</a>. Например, изомерами положения являются 1-пропанол CH<sub>3</sub>−CH<sub>2</sub>−CH<sub>2</sub>OH и 2-пропанол CH<sub>3</sub>−CH(OH)−CH<sub>3</sub>, 1-<a href="/c/buteny-713a9b" class="bre-preview-link" itemprop="url" data-external="false">бутен</a> CH<sub>2</sub>=CH−CH<sub>2</sub>−CH<sub>3</sub> и 2-бутен CH<sub>3</sub>−CH=CH−CH<sub>3</sub>. </p><p>Изменение положения функциональной группы может приводить к изменению класса соединения. Например, изомеры положения <a href="/c/atseton-0bcf9e" class="bre-preview-link" itemprop="url" data-external="false">ацетон</a> CH<sub>3</sub>−C(O)−CH<sub>3</sub> и пропаналь CH<sub>3</sub>−CH<sub>2</sub>−CHO относятся соответственно к <a href="/c/ketony-9abc48" class="bre-preview-link" itemprop="url" data-external="false">кетонам</a> и <a href="/c/al-degidy-cc9721" class="bre-preview-link" itemprop="url" data-external="false">альдегидам</a>. Структурные изомеры с разными функциональными группами сильно различаются по химическим свойствам.</p><p>Часто различия в изомерах определяют несколько структурных признаков. Например, метилизопропилкетон (3-метил-2-бутанон) CH<sub>3</sub>−C(O)−CH(CH<sub>3</sub>)<sub>2</sub> и валериановый альдегид (пентаналь) CH<sub>3</sub>−CH<sub>2</sub>−CH<sub>2</sub>−CH<sub>2</sub>−CHO отличаются друг от друга как структурой углеродного скелета, так и положением функциональной группы.</p><h4 id="h4_metametriya">Метаметрия</h4><p>Метамерия обусловлена различным положением <a href="/c/geteroatomy-1501f4" class="bre-preview-link" itemprop="url" data-external="false">гетероатома</a> (O, N, S) в цепи. Например, метамерами являются метилпропиловый эфир CH<sub>3</sub>−O−CH<sub>2</sub>−CH<sub>2</sub>−CH<sub>3</sub> и <a href="/c/dietilovyi-efir-24e6c1" class="bre-preview-link" itemprop="url" data-external="false">диэтиловый эфир</a> CH<sub>3</sub>−CH<sub>2</sub>−O−CH<sub>2</sub>−CH<sub>3</sub>, диэтиламин CH<sub>3</sub>−CH<sub>2</sub>−NH−CH<sub>2</sub>−CH<sub>3</sub> и метилпропиламин CH<sub>3</sub>−NH−CH<sub>2</sub>−CH<sub>2</sub>−CH<sub>3</sub>.</p><h4 id="h4_tautomeriya">Таутомерия</h4><p>Особым видом структурной изомерии является <a href="/c/tautomeriia-880917" class="bre-preview-link" itemprop="url" data-external="false">таутомерия</a> (равновесная динамическая изомерия). В этом случае изомеры, различающиеся функциональными группами, легко переходят друг в друга до достижения равновесия, при котором вещество одновременно содержит молекулы таутомеров в определённом соотношении.</p><h3 id="h3_prostranstvennaya_izomeriya">Пространственная изомерия</h3><p>Пространственная изомерия подразделяется на геометрическую (<i>цис</i>-<i>транс-</i>, <i>син</i>-<i>анти</i>- и E-Z-изомерию) и оптическую.</p><h4 id="h4_geometricheskaya_izomeriya">Геометрическая изомерия</h4><p>Геометрическая изомерия характерна для соединений, содержащих двойные связи или неароматические циклы, являющиеся структурно жёсткими фрагментами молекул. У <i>цис</i>-изомеров 2 заместителя расположены по одну сторону плоскости двойной связи или цикла, у <i>транс</i>-изомеров – по разные стороны. Например, геометрическими изомерами являются <i>цис</i>-2-бутен (формула V) и <i>транс</i>-2-бутен (VI), <i>цис</i>-1,2-дихлорциклопропан (VII) и <i>транс</i>-1,2-дихлорциклопропан (VIII).</p><p></p><p><span class="bre-media-image _note-exclude" data-width="75%" data-display="block"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Геометрические изомеры (цис-транс-изомеры)"><meta itemprop="caption" content="Геометрические изомеры (цис-транс-изомеры)."><meta itemprop="copyrightNotice" content="Архив БРЭ"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=OhyuK0W2i_VpFPYJL1IelQ&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Геометрические изомеры (цис-транс-изомеры)" data-nuxt-img sizes="640px" srcset="https://i.bigenc.ru/resizer/resize?sign=OhyuK0W2i_VpFPYJL1IelQ&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=4QzoCLyoMPTirZ4h82ZRBw&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=XRMFefOGiHwlT1V-AWb6Tw&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=VxZUJm1r_ojsC8EWT9D9Iw&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=TkkVSShXoC4ZeNqrNktYFg&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=TlHDY09uzovlMQuA4qBDvA&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=eKXUvIUYV6SW0_KFCC4JDA&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=RcYA9UquFsLzSiMDt9dlPA&filename=vault/daa31911f3e1442c0a52f4b559aaf0ca.webp&width=1920 1920w" title="Геометрические изомеры (цис-транс-изомеры)" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Геометрические изомеры (цис-транс-изомеры).</span><span style="display:none;" class=""><span>Геометрические изомеры (цис-транс-изомеры).</span></span></span></span></span></span></span></span>Характерными различиями между <i>цис-</i> и <i>транс-</i>изомерами являются более низкая температура плавления <i>цис</i>-изомеров, значительно лучшая <a href="/c/rastvorimost-742b41" class="bre-preview-link" itemprop="url" data-external="false">растворимость</a> в <a href="/c/voda-07375d" class="bre-preview-link" itemprop="url" data-external="false">воде</a> и явно выраженный <a href="/c/elektricheskii-dipol-nyi-moment-871e48" class="bre-preview-link" itemprop="url" data-external="false">дипольный момент</a>. <i>транс</i>-Изомеры обычно более стабильны (например, <a href="/c/maleinovaia-i-fumarovaia-kisloty-f03159" class="bre-preview-link" itemprop="url" data-external="false">малеиновая и фумаровая кислоты</a>).</p><p>Геометрическую изомерию, наблюдаемую для соединений с двойными связями C=N (<a href="/c/oksimy-ea73d8" class="bre-preview-link" itemprop="url" data-external="false">оксимы</a>) и N=N (<a href="/c/azosoedineniia-b3cd2e" class="bre-preview-link" itemprop="url" data-external="false">азосоединения</a>, <a href="/c/azoksisoedineniia-bc98e4" class="bre-preview-link" itemprop="url" data-external="false">азоксисоединения</a>), часто называют <i>син-анти</i>-изомерией. Например, геометрическими изомерами являются <i>анти</i>-бензальдоксим (формула IX) и <i>син</i>-бензальдоксим (X); <i>син</i>-<a href="/c/azobenzol-e56c63" class="bre-preview-link" itemprop="url" data-external="false">азобензол</a> (XI) и <i>анти</i>-азобензол (XII).</p><p></p><p><span class="bre-media-image _note-exclude" data-width="75%" data-display="block"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Геометрическая изомерия (син-анти-изомеры)"><meta itemprop="caption" content="Геометрическая изомерия (син-анти-изомеры)."><meta itemprop="copyrightNotice" content="Архив БРЭ"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=O7Ds0c_0TpNFNmYRDuZxaw&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Геометрическая изомерия (син-анти-изомеры)" data-nuxt-img sizes="640px" srcset="https://i.bigenc.ru/resizer/resize?sign=O7Ds0c_0TpNFNmYRDuZxaw&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=ZjOUhwEDtIP0xZHYKAPWvQ&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=Tadj6CfuqZOf7gwCocQvLQ&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=cgcI89gN9_AOf8b0mvoKjA&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=p5eseMFvgbBS320W-NyK2w&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=J8_PKsycXlYvwPB69IYVlw&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=npGan2E20KpICwLFbwLRIA&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=TjQxHSmhhHenQUSbkfnj4w&filename=vault/51eefdd986cff8c23a9c4726257a3eaf.webp&width=1920 1920w" title="Геометрическая изомерия (син-анти-изомеры)" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Геометрическая изомерия (син-анти-изомеры).</span><span style="display:none;" class=""><span>Геометрическая изомерия (син-анти-изомеры).</span></span></span></span></span></span></span></span>В общем случае используется E,Z-номенклатура. У Z-изомеров старшие заместители (имеющие больший атомный номер) расположены по одну сторону двойной связи или цикла, у E-изомеров – по разные стороны. Например, геометрическими изомерами являются Z-1-бром-1-иод-2-хлорэтилен (формула XIII) и E-1-бром-1-иод-2-хлорэтилен (XIV).</p><p><span class="bre-media-image _note-exclude" data-width="75%" data-display="block"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Геометрическая изомерия (E-Z-изомеры)"><meta itemprop="caption" content="Геометрическая изомерия (E-Z-изомеры)."><meta itemprop="copyrightNotice" content="Архив БРЭ"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=ek_VEO-ahr63jy2WP8vsTQ&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Геометрическая изомерия (E-Z-изомеры)" data-nuxt-img sizes="640px" srcset="https://i.bigenc.ru/resizer/resize?sign=ek_VEO-ahr63jy2WP8vsTQ&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=YSa0b6VaTPmiqV6r7cOjXQ&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=j2SuLLQSQ5KPSfIbb_OCPg&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=nkObyxNy7q8kl2_l411YjA&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=Z8p3bwJPFwR4Zwkj3hWIog&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=J6ybS7DdjE2-pJNLtXQeuw&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=hp4lqTj_N68aJzs9afK2Zg&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=JAGlbpf9-E1yTncQnPFTog&filename=vault/09d2482c706f80219cab3e33cd3a3dd8.webp&width=1920 1920w" title="Геометрическая изомерия (E-Z-изомеры)" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Геометрическая изомерия (E-Z-изомеры).</span><span style="display:none;" class=""><span>Геометрическая изомерия (E-Z-изомеры).</span></span></span></span></span></span></span></span></p><h4 id="h4_opticheskaya_izomeriya">Оптическая изомерия</h4><p><span class="bre-media-image _note-exclude" data-width="25%" data-display="right"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Луи Пастер"><meta itemprop="caption" content="Луи Пастер. Фото: Надар."><meta itemprop="copyrightNotice" content="Wellcome Collection"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=oXwVCgQBf9rQ3uMAd4Ef8A&filename=vault/04afdbb1824c1dc9c097b9e7ca7c3675.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Луи Пастер" data-nuxt-img sizes="320px" srcset="https://i.bigenc.ru/resizer/resize?sign=oXwVCgQBf9rQ3uMAd4Ef8A&filename=vault/04afdbb1824c1dc9c097b9e7ca7c3675.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=bFzA4LyPNZuO-400fQBdDA&filename=vault/04afdbb1824c1dc9c097b9e7ca7c3675.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=VZmduYcDAAPx6L53QvAAgQ&filename=vault/04afdbb1824c1dc9c097b9e7ca7c3675.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=TWAXDXWNjeki4FLRFWVH-w&filename=vault/04afdbb1824c1dc9c097b9e7ca7c3675.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=p2Len1UPoZXfdqFMRkjzTA&filename=vault/04afdbb1824c1dc9c097b9e7ca7c3675.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=92OxkEHEdqx4p_WlbIGWOg&filename=vault/04afdbb1824c1dc9c097b9e7ca7c3675.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=kQxbnba9DslFMVC3z56GcQ&filename=vault/04afdbb1824c1dc9c097b9e7ca7c3675.webp&width=1280 1280w" title="Луи Пастер" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Луи Пастер. Фото: Надар.</span><span style="display:none;" class=""><span>Луи Пастер. Фото: Надар.</span></span></span></span></span></span></span></span>Оптическая изомерия характерна для соединений, молекулы которых имеют элементы <a href="/c/khiral-nost-v-khimii-a3a875" class="bre-preview-link" itemprop="url" data-external="false">хиральности</a>, например <a href="/c/asimmetricheskii-atom-ugleroda-9578d1" class="bre-preview-link" itemprop="url" data-external="false">асимметрический</a> (хиральный) атом углерода, связанный с четырьмя разными заместителями. Впервые обнаружена <a href="/c/paster-lui-5b2f8d" class="bre-preview-link" itemprop="url" data-external="false">Л. Пастером</a> в 1848 г. на примере <a href="/c/vinnye-kisloty-0b9428" class="bre-preview-link" itemprop="url" data-external="false">винных кислот</a> и объяснена <a href="/c/vant-goff-iakob-khendrik-bff534" class="bre-preview-link" itemprop="url" data-external="false">Я. Х. Вант-Гоффом</a> и <a href="/c/le-bel-zhozef-ashil-2214a3" class="bre-preview-link" itemprop="url" data-external="false">Ж. А. Ле Белем</a> в 1874 г. на основе представлений о тетраэдрической конфигурации углеродных атомов в насыщенных соединениях.</p><p>Молекулы, содержащие асимметрический атом углерода, могут быть представлены в виде двух оптических изомеров, которые не могут быть совмещены в пространстве (т. е. относятся друг к другу как предмет к своему зеркальному изображению). Такие зеркальные изомеры, отличающиеся лишь противоположным расположением одних и тех же заместителей у хирального центра, называются <a href="/c/enantiomery-a2bac8" class="bre-preview-link" itemprop="url" data-external="false">энантиомерами</a>. Например, энантиомеры <a href="/c/molochnaia-kislota-25f1ae" class="bre-preview-link" itemprop="url" data-external="false">молочной кислоты</a> (XV и XVI) можно представить в трёхмерном изображении или в виде <a href="/c/formuly-fishera-99d30d" class="bre-preview-link" itemprop="url" data-external="false">формул Фишера</a>.</p><p><span class="bre-media-image _note-exclude" data-width="75%" data-display="block"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Энантиомеры молочной кислоты в трёхмерном изображении и в виде формул Фишера"><meta itemprop="caption" content="Энантиомеры молочной кислоты в трёхмерном изображении и в виде формул Фишера."><meta itemprop="copyrightNotice" content="Архив БРЭ"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=KVgBvfHj1c1dvc8NuoADzg&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Энантиомеры молочной кислоты в трёхмерном изображении и в виде формул Фишера" data-nuxt-img sizes="640px" srcset="https://i.bigenc.ru/resizer/resize?sign=KVgBvfHj1c1dvc8NuoADzg&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=LokI2ijmqWuUlQ5bHUht6g&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=7pwtKItS27cjyk_wo6eu_A&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=6PtchK2maR5CIkPe5IA5AQ&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=0i8XSFVMhA0z9o9K70eVHg&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=ti07t9lrQlt4v5874YnJ0A&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=uE5DZGCK1EdujWJIItni7g&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=8TdgImcHG0oqkL3ORPLuEA&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=1920 1920w" title="Энантиомеры молочной кислоты в трёхмерном изображении и в виде формул Фишера" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Энантиомеры молочной кислоты в трёхмерном изображении и в виде формул Фишера.</span><span style="display:none;" class=""><span>Энантиомеры молочной кислоты в трёхмерном изображении и в виде формул Фишера.</span></span></span></span></span></span></span></span>Энантиомеры имеют различную биологическую активность; для них характерна также <a href="/c/opticheskaia-aktivnost-ed7f41" class="bre-preview-link" itemprop="url" data-external="false">оптическая активность</a> – способность воздействовать на плоскополяризованный свет (вращать <a href="/c/vrashchenie-ploskosti-poliarizatsii-sveta-a50eb5" class="bre-preview-link" itemprop="url" data-external="false">плоскость поляризации</a>). Энантиомеры вращают плоскость поляризации на один и тот же угол, но в противоположном направлении, поэтому их называют оптическими антиподами.</p><p>Длительное время конфигурацию энантиомеров определяли относительно конфигурации известного стандарта, которым служили энантиомеры глицеринового альдегида (D,L-стерические ряды). Более универсальной является R,S-номенклатура (предложена <a href="/c/kan-robert-sidni-e52288" class="bre-preview-link" itemprop="url" data-external="false">Р. С. Каном</a>, <a href="/c/ingold-kristofer-kelk-abb843" class="bre-preview-link" itemprop="url" data-external="false">К. К. Инголдом</a> и <a href="/c/prelog-vladimir-1ba4f9" class="bre-preview-link" itemprop="url" data-external="false">В. Прелогом</a>), устанавливающая абсолютную конфигурацию пространственных изомеров. В соответствии с правилами R,S-номенклатуры энантиомеры молочной кислоты (XV, XVI) являются соответственно (R)-молочной и (S)-молочной кислотами. Правил перевода D,L-номенклатуры в R,S-систему не существует, т. к. в этих номенклатурах используются разные принципы. Не установлено также связи между абсолютной конфигурацией и параметрами оптического вращения.</p><p>Процесс взаимопревращения энантиомеров называется рацемизацией. Смесь равных количеств оптических антиподов – рацемическая смесь, или <a href="/c/ratsemat-06fa4a" class="bre-preview-link" itemprop="url" data-external="false">рацемат</a>, – не обладает оптической активностью. Стереоизомерии уделяется большое внимание при изучении <a href="/c/khimiia-prirodnykh-soedinenii-4ab9ba" class="bre-preview-link" itemprop="url" data-external="false">природных соединений</a> и синтезе <a href="/c/biologicheski-aktivnoe-veshchestvo-a85b26" class="bre-preview-link" itemprop="url" data-external="false">биологически активных веществ</a>. Веществам природного происхождения, содержащим элементы хиральности, присуща определённая стереоконфигурация, а также оптическая активность. При формировании хирального центра в условиях химического синтеза (за исключением <a href="/c/asimmetricheskii-sintez-7c0502" class="bre-preview-link" itemprop="url" data-external="false">асимметрического синтеза</a>) образуется рацемат; для выделения энантиомеров требуется применение сложных методов разделения рацемата на оптически активные компоненты.</p><h4 id="h4_diastereomeriya">Диастереомерия</h4><p>Для соединений, имеющих n хиральных центров в молекуле, количество возможных стереоизомеров составляет 2<sup>n</sup>. Однако при n⩾2 существуют стереоизомеры, которые отличаются друг от друга частью имеющихся в них элементов хиральности. Такие стереоизомеры, не являющиеся энантиомерами, называют диастереомерами. Например, для хлоряблочной кислоты, имеющей 2 асимметрических атома углерода, существуют 4 стереоизомера (формулы XVII–XX), среди которых пáры XVII и XVIII, а также XIX и XX являются энантиомерами, остальные пáры (XVII и XIX, XVII и XX, XVIII и XIX, XVIII и XX) – диастереомерами.</p><p><span class="bre-media-image _note-exclude" data-width="75%" data-display="block"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Стереоизомеры хлоряблочной кислоты"><meta itemprop="caption" content="Стереоизомеры хлоряблочной кислоты."><meta itemprop="copyrightNotice" content="Архив БРЭ"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=7S50G5Iq2uWm8t_jD6K_mA&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Стереоизомеры хлоряблочной кислоты" data-nuxt-img sizes="640px" srcset="https://i.bigenc.ru/resizer/resize?sign=7S50G5Iq2uWm8t_jD6K_mA&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=beuNOxX7B2i6In3UylC6Lw&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=aUGdg-h9YsIF5GZQCZBulg&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=YQeT0_UC7LkaOQWKHtwGKw&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=Lt1aENX2JVn4bIi4xgy5fA&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=oqYua9gf6fbvfdD2HjY9jw&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=gnsATEZqucZ1EHFmKRQgCg&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=Alpy92V2QW72BRWZGbCz2A&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=1920 1920w" title="Стереоизомеры хлоряблочной кислоты" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Стереоизомеры хлоряблочной кислоты.</span><span style="display:none;" class=""><span>Стереоизомеры хлоряблочной кислоты.</span></span></span></span></span></span></span></span>При появлении дополнительных элементов симметрии (плоскости, оси или центра симметрии) общее число стереоизомеров, а также количество оптически активных форм может уменьшаться. Например, винные кислоты имеют 3 стереоизомера, из них 2 оптически активные: D-винная кислота, или (2R,3R)-винная кислота (формула XXI), и L-винная кислота, или (2S,3S)-винная кислота (XXII), являющиеся энантиомерами. Их диастереомер – мезовинная кислота, или (2R,3S)-винная кислота (формула XXIII, или идентичная конфигурация XXIV), вследствие наличия плоскости симметрии (обозначена пунктиром) оптически недеятельна – является т. н. внутримолекулярным рацематом.</p><p><span class="bre-media-image _note-exclude" data-width="75%" data-display="block"><span class="bre-media-figure _note-exclude" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container"><meta itemprop="name" content="Стереоизомеры винной кислоты"><meta itemprop="caption" content="Стереоизомеры винной кислоты."><meta itemprop="copyrightNotice" content="Архив БРЭ"><span class="tw-flex tw-w-full" style=""><img src="https://i.bigenc.ru/resizer/resize?sign=OCO7KIb79bUbTQtNpDfQQg&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=120" onerror="this.setAttribute('data-error', 1)" alt="Стереоизомеры винной кислоты" data-nuxt-img sizes="640px" srcset="https://i.bigenc.ru/resizer/resize?sign=OCO7KIb79bUbTQtNpDfQQg&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=OVA-hP3gGqZ4aEgURZpSIQ&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=dNVNrojqlSMqqQx91ife3w&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=gBtYSFqfMyebfrTJtGLvSw&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=FSB4h-d2V3xl7BrSWPtxCw&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=xwPW0CmcttPXt4YMhY5g2Q&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=j4sE1SLEKXK6-_3Pn4vjhA&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=yxEDLw7E9iHu64dxnsOlQA&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=1920 1920w" title="Стереоизомеры винной кислоты" class="" itemprop="contentUrl"></span></span><span class="bre-media-caption"><span class="bre-media-caption-content"><span class="bre-media-caption__text"><span data-v-tippy><span class="tw-line-clamp-3">Стереоизомеры винной кислоты.</span><span style="display:none;" class=""><span>Стереоизомеры винной кислоты.</span></span></span></span></span></span></span></span></p><h4 id="h4_povorotnaya_izomeriya">Поворотная изомерия</h4><p>В результате <a href="/c/vnutrennee-vrashchenie-molekul-775dbc" class="bre-preview-link" itemprop="url" data-external="false">внутреннего вращения молекул</a> возникают конформационные изомеры, или конформеры, различающиеся степенью поворота фрагментов молекулы относительно одной или нескольких простых связей. В некоторых случаях можно выделить отдельные конформеры, иногда называемые также поворотными изомерами. Для изучения образования, различия в свойствах и реакционной способности конформеров используется <a href="/c/konformatsionnyi-analiz-8edb26" class="bre-preview-link" itemprop="url" data-external="false">конформационный анализ</a>.</p><span class="author _note-exclude"><span itemscope itemprop="author" itemtype="https://schema.org/Person"><span itemprop="name">В. В. Москва. </span></span>Первая публикация: Большая российская энциклопедия, 2008.</span></section></section></div><span class="bre-inline-menu _article-meta" style=""><meta itemprop="description" content="Изомери́я, явление, заключающееся в существовании химических соединений, одинаковых по составу, с одинаковой молекулярной массой, но различающихся по..."><span><span class="bre-inline-menu__item _article-meta max-md:tw-block">Опубликовано <span itemprop="datePublished">26 июня 2023 г. в 14:21 (GMT+3). </span></span><span class="bre-inline-menu__item _article-meta max-md:tw-block"> Последнее обновление <span itemprop="dateModified">28 сентября 2023 г. в 18:21 (GMT+3).</span></span></span><span class="-flex-divider"></span><span class="bre-inline-menu__item tw-items-start"><button type="button" class="b-button tw-gap-2 b-button--link -text-button-text tw-rounded-lg tw-cursor-pointer" data-v-cfbedafc><span class="c-button__content" data-v-cfbedafc>Связаться с редакцией</span></button></span></span></div></div><div class="bre-tags-wrap"><span data-v-063d9480><a href="/l/nauchnye-terminy-v-organicheskoi-khimii-4f05b9" class="bre-article-tag bre-article-tag__link _default _no-border" data-v-063d9480>#Научные термины в органической химии</a></span><span data-v-063d9480><a href="/l/nauchnye-terminy-v-neorganicheskoi-khimii-af08b8" class="bre-article-tag bre-article-tag__link _default _no-border" data-v-063d9480>#Научные термины в неорганической химии</a></span><span data-v-063d9480><a href="/l/khimicheskie-zakony-df1c72" class="bre-article-tag bre-article-tag__link _default _no-border" data-v-063d9480>#Химические законы</a></span><span data-v-063d9480><a href="/l/khimicheskie-teorii-b6d260" class="bre-article-tag bre-article-tag__link _default _no-border" data-v-063d9480>#Химические теории</a></span></div></div><aside class="bre-article-page__sidebar -show-on-desktop-s" style=""><nav class="bre-article-loc lg:tw-sticky"><div class="bre-article-loc-button"><span class="bre-article-loc-title">Содержание</span><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-primary-black"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"><path d="M6 9l6 6 6-6" stroke="currentColor" stroke-width="1.5" stroke-linecap="round"/></svg> </span><div class="bre-article-loc-short">Историческая справка</div></div></nav><div class="bre-article-page__sidebar-wrapper"><div class="article-sidebar"><div class="article-sidebar-button -show-on-tablet -hide-on-desktop-s"><span class="article-sidebar-title">Информация</span><span class="nuxt-icon _no-icon-margin tw-text-2xl tw-text-primary-black"><svg viewBox="0 0 24 24" fill="none" xmlns="http://www.w3.org/2000/svg"><path d="M6 9l6 6 6-6" stroke="currentColor" stroke-width="1.5" stroke-linecap="round"/></svg> </span><div class="article-sidebar-text -show-on-tablet -hide-on-desktop-s"></div></div><div class="article-sidebar-wrapper -hide-on-tablet"><span class="bre-media-image article-sidebar-image _note-exclude _clean" data-width="100%" data-display="block"><span class="bre-media-figure _note-exclude _clean" itemscope itemtype="https://schema.org/ImageObject" itemprop="image"><span class="bre-media-image-container _placeholder"><meta itemprop="name" content="Химия"><meta itemprop="caption" content="Химия. 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Такие зеркальные изомеры, отличающиеся лишь противоположным расположением одних и тех же заместителей у хирального центра, называются ",{"attrs":10,"content":10,"marks":1320,"text":1326,"type":48},[1321],{"attrs":1322,"content":10,"marks":10,"text":13,"type":62},{"content_id":1323,"external":12,"graph_link":6,"href":56,"kind_id":57,"link":1324,"link_type":74,"navigation_value":10,"target":13,"version":45},"a2bac88b-8de3-4454-b6a4-6546350460a4",{"slug":1325,"type":60},"enantiomery-a2bac8","энантиомерами",{"attrs":10,"content":10,"marks":10,"text":1328,"type":48},". Например, энантиомеры ",{"attrs":10,"content":10,"marks":1330,"text":1336,"type":48},[1331],{"attrs":1332,"content":10,"marks":10,"text":13,"type":62},{"content_id":1333,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1334,"link_type":74,"navigation_value":10,"target":13,"version":45},"25f1ae34-0ff1-4aea-8f10-f60722500472",{"slug":1335,"type":60},"molochnaia-kislota-25f1ae","молочной кислоты",{"attrs":10,"content":10,"marks":10,"text":1338,"type":48}," (XV и XVI) можно представить в трёхмерном изображении или в виде ",{"attrs":10,"content":10,"marks":1340,"text":1347,"type":48},[1341],{"attrs":1342,"content":10,"marks":10,"text":13,"type":62},{"content_id":1343,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1344,"link_type":1346,"navigation_value":10,"target":13,"version":45},"99d30d12-cd8a-46ca-9775-3ae25f43c8e6",{"slug":1345,"type":60},"formuly-fishera-99d30d","27","формул Фишера",{"attrs":10,"content":10,"marks":10,"text":160,"type":48},{"attrs":1350,"content":1351,"marks":10,"text":13,"type":161},{"textAlign":10},[1352,1362,1364,1372,1374,1382],{"attrs":1353,"content":10,"marks":1359,"text":13,"type":188},{"alt":13,"caption":1354,"copyright":565,"copyrightLink":13,"display":566,"ref_id":1355,"src":1356,"srcset":1357,"storage_link":13,"text":1354,"title":1358,"ts_expire":181,"width":571},"Энантиомеры молочной кислоты в трёхмерном изображении и в виде формул Фишера.","75758406-eacf-4e7d-9c44-bc006a19c684","https://i.bigenc.ru/resizer/resize?sign=KVgBvfHj1c1dvc8NuoADzg&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=120","https://i.bigenc.ru/resizer/resize?sign=KVgBvfHj1c1dvc8NuoADzg&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=LokI2ijmqWuUlQ5bHUht6g&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=7pwtKItS27cjyk_wo6eu_A&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=6PtchK2maR5CIkPe5IA5AQ&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=0i8XSFVMhA0z9o9K70eVHg&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=ti07t9lrQlt4v5874YnJ0A&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=uE5DZGCK1EdujWJIItni7g&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=8TdgImcHG0oqkL3ORPLuEA&filename=vault/1e77faaa5f5726d81ad7ceded982dcfe.webp&width=1920 1920w","Энантиомеры молочной кислоты в трёхмерном изображении и в виде формул Фишера",[1360],{"attrs":1361,"content":10,"marks":10,"text":13,"type":187},{"caption":1354,"display":566,"style":575,"version":45},{"attrs":10,"content":10,"marks":10,"text":1363,"type":48},"Энантиомеры имеют различную биологическую активность; для них характерна также ",{"attrs":10,"content":10,"marks":1365,"text":1371,"type":48},[1366],{"attrs":1367,"content":10,"marks":10,"text":13,"type":62},{"content_id":1368,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1369,"link_type":106,"navigation_value":10,"target":13,"version":45},"ed7f41fa-3414-4a71-898d-f61561c93d34",{"slug":1370,"type":60},"opticheskaia-aktivnost-ed7f41","оптическая активность",{"attrs":10,"content":10,"marks":10,"text":1373,"type":48}," – способность воздействовать на плоскополяризованный свет (вращать ",{"attrs":10,"content":10,"marks":1375,"text":1381,"type":48},[1376],{"attrs":1377,"content":10,"marks":10,"text":13,"type":62},{"content_id":1378,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1379,"link_type":585,"navigation_value":10,"target":13,"version":45},"a50eb58f-6530-4687-b78a-3655896c0115",{"slug":1380,"type":60},"vrashchenie-ploskosti-poliarizatsii-sveta-a50eb5","плоскость поляризации",{"attrs":10,"content":10,"marks":10,"text":1383,"type":48},"). Энантиомеры вращают плоскость поляризации на один и тот же угол, но в противоположном направлении, поэтому их называют оптическими антиподами.",{"attrs":1385,"content":1386,"marks":10,"text":13,"type":161},{"textAlign":10},[1387,1389,1397,1398,1406,1407,1415],{"attrs":10,"content":10,"marks":10,"text":1388,"type":48},"Длительное время конфигурацию энантиомеров определяли относительно конфигурации известного стандарта, которым служили энантиомеры глицеринового альдегида (D,L-стерические ряды). Более универсальной является R,S-номенклатура (предложена ",{"attrs":10,"content":10,"marks":1390,"text":1396,"type":48},[1391],{"attrs":1392,"content":10,"marks":10,"text":13,"type":62},{"content_id":1393,"external":12,"graph_link":6,"href":56,"kind_id":57,"link":1394,"link_type":137,"navigation_value":10,"target":13,"version":45},"e5228875-4a2e-4fa4-8d04-2f447d6b5742",{"slug":1395,"type":60},"kan-robert-sidni-e52288","Р. С. Каном",{"attrs":10,"content":10,"marks":10,"text":990,"type":48},{"attrs":10,"content":10,"marks":1399,"text":1405,"type":48},[1400],{"attrs":1401,"content":10,"marks":10,"text":13,"type":62},{"content_id":1402,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1403,"link_type":137,"navigation_value":10,"target":13,"version":45},"abb84314-b7c8-4b0c-ac1e-c5a808dc80c2",{"slug":1404,"type":60},"ingold-kristofer-kelk-abb843","К. К. Инголдом",{"attrs":10,"content":10,"marks":10,"text":210,"type":48},{"attrs":10,"content":10,"marks":1408,"text":1414,"type":48},[1409],{"attrs":1410,"content":10,"marks":10,"text":13,"type":62},{"content_id":1411,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1412,"link_type":137,"navigation_value":10,"target":13,"version":45},"1ba4f92b-af73-41cc-8cde-65521b91f4b6",{"slug":1413,"type":60},"prelog-vladimir-1ba4f9","В. Прелогом",{"attrs":10,"content":10,"marks":10,"text":1416,"type":48},"), устанавливающая абсолютную конфигурацию пространственных изомеров. В соответствии с правилами R,S-номенклатуры энантиомеры молочной кислоты (XV, XVI) являются соответственно (R)-молочной и (S)-молочной кислотами. Правил перевода D,L-номенклатуры в R,S-систему не существует, т. к. в этих номенклатурах используются разные принципы. Не установлено также связи между абсолютной конфигурацией и параметрами оптического вращения.",{"attrs":1418,"content":1419,"marks":10,"text":13,"type":161},{"textAlign":10},[1420,1422,1430,1432,1440,1442,1450,1452,1460],{"attrs":10,"content":10,"marks":10,"text":1421,"type":48},"Процесс взаимопревращения энантиомеров называется рацемизацией. Смесь равных количеств оптических антиподов – рацемическая смесь, или ",{"attrs":10,"content":10,"marks":1423,"text":1429,"type":48},[1424],{"attrs":1425,"content":10,"marks":10,"text":13,"type":62},{"content_id":1426,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1427,"link_type":106,"navigation_value":10,"target":13,"version":45},"06fa4a65-1ff3-48a8-9e7c-4998ac671ff4",{"slug":1428,"type":60},"ratsemat-06fa4a","рацемат",{"attrs":10,"content":10,"marks":10,"text":1431,"type":48},", – не обладает оптической активностью. Стереоизомерии уделяется большое внимание при изучении ",{"attrs":10,"content":10,"marks":1433,"text":1439,"type":48},[1434],{"attrs":1435,"content":10,"marks":10,"text":13,"type":62},{"content_id":1436,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1437,"link_type":585,"navigation_value":10,"target":13,"version":45},"4ab9badc-6366-413e-93a4-6fd5daa4353e",{"slug":1438,"type":60},"khimiia-prirodnykh-soedinenii-4ab9ba","природных соединений",{"attrs":10,"content":10,"marks":10,"text":1441,"type":48}," и синтезе ",{"attrs":10,"content":10,"marks":1443,"text":1449,"type":48},[1444],{"attrs":1445,"content":10,"marks":10,"text":13,"type":62},{"content_id":1446,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1447,"link_type":585,"navigation_value":10,"target":13,"version":45},"a85b2673-5ad1-4667-959f-c3fb8cd7767c",{"slug":1448,"type":60},"biologicheski-aktivnoe-veshchestvo-a85b26","биологически активных веществ",{"attrs":10,"content":10,"marks":10,"text":1451,"type":48},". Веществам природного происхождения, содержащим элементы хиральности, присуща определённая стереоконфигурация, а также оптическая активность. При формировании хирального центра в условиях химического синтеза (за исключением ",{"attrs":10,"content":10,"marks":1453,"text":1459,"type":48},[1454],{"attrs":1455,"content":10,"marks":10,"text":13,"type":62},{"content_id":1456,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1457,"link_type":585,"navigation_value":10,"target":13,"version":45},"7c05029c-96a0-4a01-afef-1b386593c29c",{"slug":1458,"type":60},"asimmetricheskii-sintez-7c0502","асимметрического синтеза",{"attrs":10,"content":10,"marks":10,"text":1461,"type":48},") образуется рацемат; для выделения энантиомеров требуется применение сложных методов разделения рацемата на оптически активные компоненты.",{"attrs":1463,"content":1465,"marks":10,"text":13,"type":290},{"textAlign":10,"version":45,"id":1464},"h4_diastereomeriya",[1466],{"attrs":10,"content":10,"marks":10,"text":1467,"type":48},"Диастереомерия",{"attrs":1469,"content":1470,"marks":10,"text":13,"type":161},{"textAlign":10},[1471,1473,1479],{"attrs":10,"content":10,"marks":10,"text":1472,"type":48},"Для соединений, имеющих n хиральных центров в молекуле, количество возможных стереоизомеров составляет 2",{"attrs":10,"content":10,"marks":1474,"text":1478,"type":48},[1475],{"attrs":1476,"content":10,"marks":10,"text":13,"type":1477},{"version":45},"sup","n",{"attrs":10,"content":10,"marks":10,"text":1480,"type":48},". Однако при n⩾2 существуют стереоизомеры, которые отличаются друг от друга частью имеющихся в них элементов хиральности. Такие стереоизомеры, не являющиеся энантиомерами, называют диастереомерами. Например, для хлоряблочной кислоты, имеющей 2 асимметрических атома углерода, существуют 4 стереоизомера (формулы XVII–XX), среди которых пáры XVII и XVIII, а также XIX и XX являются энантиомерами, остальные пáры (XVII и XIX, XVII и XX, XVIII и XIX, XVIII и XX) – диастереомерами.",{"attrs":1482,"content":1483,"marks":10,"text":13,"type":161},{"textAlign":10},[1484,1494],{"attrs":1485,"content":10,"marks":1491,"text":13,"type":188},{"alt":13,"caption":1486,"copyright":565,"copyrightLink":13,"display":566,"ref_id":1487,"src":1488,"srcset":1489,"storage_link":13,"text":1486,"title":1490,"ts_expire":181,"width":571},"Стереоизомеры хлоряблочной кислоты.","2eafe48b-4eba-4121-b426-e90a1ab59879","https://i.bigenc.ru/resizer/resize?sign=7S50G5Iq2uWm8t_jD6K_mA&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=120","https://i.bigenc.ru/resizer/resize?sign=7S50G5Iq2uWm8t_jD6K_mA&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=beuNOxX7B2i6In3UylC6Lw&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=aUGdg-h9YsIF5GZQCZBulg&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=YQeT0_UC7LkaOQWKHtwGKw&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=Lt1aENX2JVn4bIi4xgy5fA&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=oqYua9gf6fbvfdD2HjY9jw&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=gnsATEZqucZ1EHFmKRQgCg&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=Alpy92V2QW72BRWZGbCz2A&filename=vault/321a9820c035fc649793928ef52b72fc.webp&width=1920 1920w","Стереоизомеры хлоряблочной кислоты",[1492],{"attrs":1493,"content":10,"marks":10,"text":13,"type":187},{"caption":1486,"display":566,"style":575,"version":45},{"attrs":10,"content":10,"marks":10,"text":1495,"type":48},"При появлении дополнительных элементов симметрии (плоскости, оси или центра симметрии) общее число стереоизомеров, а также количество оптически активных форм может уменьшаться. Например, винные кислоты имеют 3 стереоизомера, из них 2 оптически активные: D-винная кислота, или (2R,3R)-винная кислота (формула XXI), и L-винная кислота, или (2S,3S)-винная кислота (XXII), являющиеся энантиомерами. Их диастереомер – мезовинная кислота, или (2R,3S)-винная кислота (формула XXIII, или идентичная конфигурация XXIV), вследствие наличия плоскости симметрии (обозначена пунктиром) оптически недеятельна – является т. н. внутримолекулярным рацематом.",{"attrs":1497,"content":1498,"marks":10,"text":13,"type":161},{"textAlign":10},[1499],{"attrs":1500,"content":10,"marks":1506,"text":13,"type":188},{"alt":13,"caption":1501,"copyright":565,"copyrightLink":13,"display":566,"ref_id":1502,"src":1503,"srcset":1504,"storage_link":13,"text":1501,"title":1505,"ts_expire":181,"width":571},"Стереоизомеры винной кислоты.","e42a080d-ebee-4c12-8c02-02b0a57b5e34","https://i.bigenc.ru/resizer/resize?sign=OCO7KIb79bUbTQtNpDfQQg&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=120","https://i.bigenc.ru/resizer/resize?sign=OCO7KIb79bUbTQtNpDfQQg&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=120 120w,https://i.bigenc.ru/resizer/resize?sign=OVA-hP3gGqZ4aEgURZpSIQ&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=320 320w,https://i.bigenc.ru/resizer/resize?sign=dNVNrojqlSMqqQx91ife3w&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=480 480w,https://i.bigenc.ru/resizer/resize?sign=gBtYSFqfMyebfrTJtGLvSw&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=640 640w,https://i.bigenc.ru/resizer/resize?sign=FSB4h-d2V3xl7BrSWPtxCw&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=768 768w,https://i.bigenc.ru/resizer/resize?sign=xwPW0CmcttPXt4YMhY5g2Q&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=1024 1024w,https://i.bigenc.ru/resizer/resize?sign=j4sE1SLEKXK6-_3Pn4vjhA&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=1280 1280w,https://i.bigenc.ru/resizer/resize?sign=yxEDLw7E9iHu64dxnsOlQA&filename=vault/487641608b9fe1b2292df9aea639a3b2.webp&width=1920 1920w","Стереоизомеры винной кислоты",[1507],{"attrs":1508,"content":10,"marks":10,"text":13,"type":187},{"caption":1501,"display":566,"style":575,"version":45},{"attrs":1510,"content":1512,"marks":10,"text":13,"type":290},{"textAlign":10,"version":45,"id":1511},"h4_povorotnaya_izomeriya",[1513],{"attrs":10,"content":10,"marks":10,"text":1514,"type":48},"Поворотная изомерия",{"attrs":1516,"content":1517,"marks":10,"text":13,"type":161},{"textAlign":10},[1518,1520,1528,1530,1538],{"attrs":10,"content":10,"marks":10,"text":1519,"type":48},"В результате ",{"attrs":10,"content":10,"marks":1521,"text":1527,"type":48},[1522],{"attrs":1523,"content":10,"marks":10,"text":13,"type":62},{"content_id":1524,"external":12,"graph_link":6,"href":56,"kind_id":71,"link":1525,"link_type":849,"navigation_value":10,"target":13,"version":45},"775dbcd0-502c-4c85-a6ee-66bd508c5d30",{"slug":1526,"type":60},"vnutrennee-vrashchenie-molekul-775dbc","внутреннего вращения молекул",{"attrs":10,"content":10,"marks":10,"text":1529,"type":48}," возникают конформационные изомеры, или конформеры, различающиеся степенью поворота фрагментов молекулы относительно одной или нескольких простых связей. 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