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Conformational Studies in the Cyclohexane Series. 2. Phenylcyclohexane and 1-methyl-1-phenylcyclohexane

Conformational Studies in the Cyclohexane Series. 2. Phenylcyclohexane and 1-methyl-1-phenylcyclohexane

KB Wiberg, H Castejon, WF Bailey, J Ochterski

J Org Chem. 2000 Feb 25;65(4):1181-7.

PMID: 10814069

Abstract:

The structures and relative energies of the conformers of phenylcyclohexane, and 1-methyl-1-phenylcyclohexane have been calculated at theoretical levels including HF/6-31G, B3LYP/6-311G, MP2/6-311G, MP2/6-311(2df,p), QCISD/6-311G, and QCISD/6-311G(2df,p). The latter gives conformational enthalpy (DeltaH degrees ), entropy (DeltaS degrees ), and free energy (DeltaG degrees ) values for phenylcyclohexane that are in excellent agreement with the experimental data. The calculations for 1-methyl-1-phenylcyclohexane find a free energy difference of 1.0 kcal/mol at -100 degrees C, favoring the conformation having an axial phenyl group, that is in only modest agreement with the experimental value of 0.32 +/- 0.04 kcal/mol. The origin of the phenyl rotational profiles for the conformers of phenylcyclohexane and 1-methyl-1-phenylcyclohexane is discussed.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP827521	Phenylcyclohexane		827-52-1	Price

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