Premium
Conformational behavior of azabiphenyls
Author(s) -
Barone Vincenzo,
Lelj Francesco,
Russo Nino
Publication year - 1986
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560290326
Subject(s) - lone pair , steric effects , chemistry , hydrogen bond , molecule , basis set , attraction , benzene , computational chemistry , stereochemistry , crystallography , density functional theory , organic chemistry , linguistics , philosophy
Abstract The conformational behavior of biphenyl‐like compounds constituted by benzene and/or azabenzenes has been investigated at the STO ‐3G Hartree‐Fock level. Although the STO‐3G basis set probably overstimates conjugative attraction, it seems able to provide reliable general trends. In this connection the analysis of over 30 molecules shows that compounds with the same ortho substituents (including nitrogen lone pairs) have very similar conformational behavior, irrespective of their composition. Furthermore, the comparison of different isomers shows that repulsive interactions decrease in the order hydrogen–hydrogen > lone pair – lone pair > hydrogen lone pair. Conjugative, electrostatic, and steric interactions have also been expressed by well known semiempirical functions, thus allowing a better analysis of the overall torsional potential.