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Conformational studies of octalene and its benzo‐derivatives
Author(s) -
Favini Giorgio,
Moro Giorgio,
Todeschini Roberto,
Simonetta Massimo
Publication year - 1984
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.540050410
Subject(s) - cyclooctatetraene , chemistry , ring (chemistry) , ring flip , double bond , computational chemistry , force field (fiction) , stereochemistry , crystallography , molecule , physics , organic chemistry , quantum mechanics
Abstract Theoretical calculations by the combined empirical force‐field ( EFF )‐extended Hückel molecular orbital ( EHMO ) approach confirm that octalene and benzo‐| c |‐octalene present π‐bond fixation with a common single bond between the cyclooctatetraene and cyclooctatriene fragments, whereas the structure of dibenzo‐| c , j |‐octalene is characterized by a central double bond. The dynamic behavior of these compounds is discussed and the interconversion energy barriers are calculated; the inversion of the cyclooctatriene ring is faster than that of the cyclooctatetraene ring in octalene, but it is slower in benzo‐| c |‐octalene.