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Conformational Analysis of 1,2:3,4‐Diepoxides: Ab Initio and semiempirical molecular‐orbital calculations
Author(s) -
Nikles Martin,
Bur Daniel,
Séquin Urs,
Huber Hanspeter
Publication year - 1992
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.19920750520
Subject(s) - dihedral angle , chemistry , ab initio , computational chemistry , diastereomer , molecular orbital , crystallography , ab initio quantum chemistry methods , stereochemistry , molecule , organic chemistry , hydrogen bond
Using semiempirical and ab initio procedures, the most stable conformations of meso ‐ and rac ‐bioxirane and of some substituted 1,2:3,4‐diepoxides were calculated. For threo ‐diepoxides (having the same relative configurations as rac ‐bioxirane, 3 ), two stable conformations with CCCC dihedral angles of ca . 90 and ca. 270° were found. For erythro ‐diepoxides (derivatives of meso ‐bioxirane, 4 ) the calculations suggest three preferred conformations with corresponding dihedral CCCC angles of ca. 90°, ca. 180°, and ca. 270°. The calculations are in fair agreement with the experimental data available for the unsubstituted compounds 3 and 4 .