Isolation of rotational isomers and developments derived therefrom

被引:0
作者
Oki, Michinori [1 ,2 ]
机构
[1] Univ Tokyo, Tokyo, Japan
[2] Okayama Univ Sci, Okayama, Japan
来源
PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES | 2010年 / 86卷 / 09期
关键词
stable rotational isomers; stable conformers; chiral conformers; absolute conformation; internal compensation; RESTRICTED ROTATION; TETRAHEDRAL CARBON; STABLE ROTAMERS; STEREOCHEMICAL ANALOG; INTERNAL-ROTATION; HINDERED ROTATION; ABSOLUTE STEREOCHEMISTRY; BARRIERS; DIAZOTIZATION; SPECTROSCOPY;
D O I
10.2183/pjab.86.867
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Isolation of rotational isomer models of ethane-type molecules is described. We could experimentally prove that if rotational isomers whose molecular shape was chiral, the molecule could be optically active, even though it did not carry an asymmetric carbon atom. As an extension, other types of stereochemically fundamental and optically active molecules were isolated and their absolute stereochemistry was determined. One example is the model of meso-tartaric acid, for which optical inactivity had been attributed to internal compensation but is now explained as follows. On dissolution of meso-tartaric acid in a solvent, the molecule gives two kinds of conformers, one of which is a C-i molecule and the other is a C-i molecule. Although the latter is intrinsically optically active, the optical activity is cancelled by its enantiomer. The theory of internal compensation is recommended to be abandoned. As an extension to another area, some reactions of conformers are also discussed.
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页码:867 / 883
页数:17
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