双语化学辞典Chem Lexicon
概念 · 有机化学 · 立体化学 Organic chemistry · Stereochemistry

对映异构体Enantiomer

高中High school
拼音Pinyin duì yìng yì gòu tǐ 别名Also 对映体;旋光异构体; optical isomer旧称 / 异名 旋光异构体;光学异构体

定义Definition

对映异构体是互为镜像、但不能重合的一对立体异构体。只有手性分子才有对映异构体;最常见的情况是分子含一个连有四个不同基团的碳原子。

Enantiomers are a pair of stereoisomers that are mirror images of each other but cannot be superimposed. Only chiral molecules have enantiomers; the commonest case is a molecule with one carbon atom bonded to four different groups.

性质Properties

一对对映体的熔点、沸点、密度、溶解度和与非手性试剂的反应完全相同。不同之处在于:它们使平面偏振光旋转的角度相等、方向相反,分别称为右旋(+)和左旋(−);与其他手性物质(如酶、受体)作用时可能差别很大。等量对映体的混合物称为外消旋体,不旋光。

Enantiomers have identical melting and boiling points, density, solubility and reactions with achiral reagents. They differ in rotating plane-polarised light by equal angles in opposite directions, dextrorotatory (+) and laevorotatory (−), and they may behave very differently towards other chiral substances such as enzymes and receptors. An equal mixture is a racemate and shows no optical rotation.

表示与命名Drawing and naming

用楔形键和虚楔键表示手性碳上基团的空间取向,画出镜像即得另一对映体。每个手性中心的构型用 CIP 规则标为 R 或 S;旋光方向(+/−)需由实验测定,与 R/S 没有固定对应关系。

Wedged and hashed bonds show the arrangement of groups at a chiral carbon; drawing the mirror image gives the other enantiomer. Each centre is labelled R or S by the CIP rules; the sign of rotation (+/−) must be measured and has no fixed link to R/S.

意义Significance

生物体内的氨基酸几乎都是 L 型,糖多为 D 型,许多药物只有一种对映体有效。由非手性原料合成手性分子通常得到外消旋体,需拆分或采用不对称合成。

Amino acids in living things are almost all L and sugars mostly D, and many drugs work as only one enantiomer. Making a chiral molecule from achiral starting materials usually gives a racemate, which must be resolved, or asymmetric synthesis is used.

年表Timeline

  • 1848

    巴斯德用镊子分开酒石酸盐的左右手晶体

    Pasteur separates left- and right-handed tartrate crystals with tweezers

  • 1874

    范特霍夫与勒贝尔用四面体碳解释对映异构

    van 't Hoff and Le Bel explain enantiomers with the tetrahedral carbon

  • 2001

    诺尔斯、野依良治、夏普莱斯因不对称催化获诺贝尔化学奖

    Knowles, Noyori and Sharpless receive the Nobel Prize in Chemistry for asymmetric catalysis

相关公式Formulas

对映体过量 Enantiomeric excess→
\[ee = \frac{|n_R - n_S|}{n_R + n_S}\times 100\% \approx \frac{[\alpha]_{\text{观测}}}{[\alpha]_{\text{纯}}}\times 100\%\]\[ee = \frac{|n_R - n_S|}{n_R + n_S}\times 100\% \approx \frac{[\alpha]_{\text{obs}}}{[\alpha]_{\text{pure}}}\times 100\%\]