Relative stabilities of some synthetically useful 2,3-cis-disubstituted aziridines and their 2,3-trans isomers.
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.
Mimura
Norio
N
Faculty of Pharmaceutical Sciences, Kyoto University, Japan. Norio.Mimura@pharma.novartis.com
Miwa
Yoshihisa
Y
Ibuka
Toshiro
T
Yamamoto
Yoshinori
Y
D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry*; D004355:Drug Stability; D007202:Indicators and Reagents; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
D001388:Aziridines; D007202:Indicators and Reagents