title: Relative stabilities of some synthetically useful 2,3-cis-disubstituted aziridines and their 2,3-trans isomers.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kyoto University, Japan. Norio.Mimura@pharma.novartis.com
authors.forename: Norio
authors.initials: N
authors.lastname: Mimura
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Miwa
authors.forename: Toshiro
authors.initials: T
authors.lastname: Ibuka
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Yamamoto
mesh_terms: 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
chemical_list: D001388:Aziridines; D007202:Indicators and Reagents