Mimura Norio, Miwa Yoshihisa, Ibuka Toshiro, Yamamoto Yoshinori
Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
J Org Chem. 2002 Aug 9;67(16):5796-801. doi: 10.1021/jo025777k.
The relative stabilities of synthetically useful 2,3-cis/trans pairs of 2,3-disubstituted aziridines were investigated theoretically by performing molecular orbital calculations at the MP2/6-31G**/RHF/6-31G** level of theory. The results showed clearly that a functional group on the nitrogen atom of the aziridine ring plays a very important role in conjunction with the relative stabilities of these pairs of isomers. There is a tendency that the 2,3-cis isomer bearing tetrahedral structure on the aziridine nitrogen is preferable. Bulky substituents such as a phenyl group on aziridine atoms can also affect the relative stability sterically.
通过在MP2/6 - 31G**/RHF/6 - 31G**理论水平上进行分子轨道计算，从理论上研究了具有合成用途的2,3 - 二取代氮丙啶的2,3 - 顺式/反式异构体对的相对稳定性。结果清楚地表明，氮丙啶环氮原子上的官能团与这些异构体对的相对稳定性共同起着非常重要的作用。存在一种趋势，即氮丙啶氮上具有四面体结构的2,3 - 顺式异构体更受青睐。氮丙啶原子上的大体积取代基（如苯基）也会在空间上影响相对稳定性。
