Theoretical description of the preference of vicinal alkyl/phenyl gauche conformation by molecular mechanics. an alternative interpretation for the ch ⋯π attractive interaction
1983; Elsevier BV; Volume: 39; Issue: 19 Linguagem: Inglês
10.1016/s0040-4020(01)91550-9
ISSN1464-5416
AutoresMinoru Hirota, Toshiyuki Sekiya, Kazuhisa ABE, Hiroshi Tashiro, Makoto Karatsu, Motohiro Nishio, Eiji Ōsawa,
Tópico(s)Organic Chemistry Cycloaddition Reactions
ResumoMolecular mechanics calculations on alkyl benzyl carbinols, ketones, sulphides and sulphoxides were carried out as a function of the torsional angle about the benzyl C-O, C-S, or C-SO bond by use of the MM2 program. Theoretical consequences generally agree with the experimental results showing that the phenyl/alkyl gauche conformer is the most preferred for all 1-phenylethyl compounds and also for some of benzyl compounds investigated. Detailed examination on the energy terms revealed the contribution of attractive non-bond interaction between the alkyl and phenyl groups vicinally located in stabilizing the phenyl-alkyl gauche conformer. Thus the preference of CH ⋯π conformation can be interpreted by the contribution of the dispersive force. Possible participation of other attractive forces is discussed briefly.
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