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A computational study of azine, azoethene, and diimine linkages in the poly/oligoazine system
Author(s) -
Schmitz Brian K.,
Euler William B.
Publication year - 1994
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540151012
Subject(s) - azine , diimine , lone pair , chemistry , basis set , computational chemistry , molecular mechanics , stereochemistry , molecule , organic chemistry , molecular dynamics , density functional theory , catalysis
Hartree‐Fock (HF) and molecular mechanics calculations were performed on linear azine oligomers and model compounds. The rotational energy curves for the model compounds formaldazine, H 2 C = NN = CH 2 , ethenyl diazene, H 2 C = CHN = NH, and ethanediimine, HN = CHCH = NH were calculated for a variety of basis sets at the HF and MP2 level. In all of these cases the rotational energy barriers are quite different from butadienes or aza‐substituted butadienes because of the lone pair–lone pair interaction of the adjacent nitrogen atoms. The results on the model compounds were used to generate a set of molecular mechanics (MM) parameters that are appropriate for linear oligo‐ and polyazines. Comparison of the geometries of the HF results and MM results for the oligoazines showed that the two methods gave comparable results. © 1994 by John Wiley & Sons, Inc.