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X‐Ray Crystallographic and MO Studies on the Conformation of Corynoline and the Related Compounds
Author(s) -
Kamigauchi Miyoko,
Noda Yuko,
Takao Narao,
Ishida Toshimasa,
Inoue Masatoshi
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690614
Subject(s) - chemistry , cndo/2 , intramolecular force , crystallography , ring (chemistry) , crystal structure , x ray , twist , cyclohexane conformation , x ray crystallography , stereochemistry , crystal (programming language) , diffraction , molecule , hydrogen bond , physics , geometry , mathematics , programming language , organic chemistry , quantum mechanics , computer science , optics
The crystal structure of (±)‐corynoline ( 1 ) has been determined by X‐ray diffraction methods. The rings B and C form the half‐chair and the twist‐half‐chair conformations, respectively. The B/C ring conjunction exists in an anti ‐ cis conformation, with a N … HO intramolecular H‐bond. Conformational energy calculation by the CNDO/2 method show that the conformations of 1 , (+)‐chelidonine ( 2 ), and their acetates, observed in crystal structures, are all in the one of total energy minimum.