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Geometry and energy of overcrowded ethylenes. II. Bornanylidene, fenchylidene, and bifluorenylidene derivatives
Author(s) -
Favini G.,
Simonetta M.,
Sottocornola M.,
Todeschini R.
Publication year - 1982
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.540030208
Subject(s) - molecular geometry , chemistry , total energy , computational chemistry , strain energy , bond length , derivative (finance) , energy minimization , molecular mechanics , stereochemistry , molecule , physics , thermodynamics , molecular dynamics , organic chemistry , psychology , finite element method , economics , financial economics , displacement (psychology) , psychotherapist
The geometry and energy of some bornanylidene, fenchylidene, and bifluorenylidene derivatives have been determined by the molecular mechanics method. Low twisting of the double bond was found for the compounds of the first two series. The difficulties found in the synthesis of 2‐di‐ tert ‐butylmethylenefenchane can be related to a remarkable strain energy which is only slightly lower than that of tetra‐ tert ‐butylethylene. A twisted conformation is the preferred one in bifluorenylidene and its 1,1′‐dimethyl derivative ( E isomer) in agreement with experimental data. Conformational inversion and E–Z interconversion paths are discussed for the latter compound and theoretical results are compared with dynamic NMR data.