6533b82cfe1ef96bd128e9c0

RESEARCH PRODUCT

MINDO/3 Study of the Rearrangement of 1-Methylcyclohexyl Cation to 1,2-Dimethylcyclopentyl Cation

P.m. Viruela-martínFrancisco TomásRafael Viruela-martínIgnacio Nebot-gil

subject

Computational MathematicsAcid catalysisCycloalkanechemistry.chemical_compoundchemistryComputational chemistryGeneral ChemistryReaction intermediateCarbocationBranching (polymer chemistry)IsomerizationMINDOTransition state

description

The rearrangement of the 1-methylcyclohexyl cation to the 1,2-dimethylcyclopentyl cation has been studied by MINDO/3 calculations, as an application of the branching mechanism model for cycloalkanes. Possible intermediates and transition states have been characterized by diagonalization of their Hessian matrixes. Two nonequivalent pathways, α and β scissions, are relatively close in energy. The calculated transition states are almost equivalent in energy to those found for cyclohexyl cation. Hence, the energy barriers are higher for the rearrangement of the 1-methyl than for cyclohexyl cation, because the former is less stable than the latter.

yearjournalcountryeditionlanguage
1986-08-01Journal of Computational Chemistry
https://doi.org/10.1002/jcc.540070405