Molecular Structure and Internal Rotations of Tetracyclohexylmethane

Ishay Columbus, Silvio E. Biali*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

The stereochemistry of tetracyclohexylmethane (2), obtained by catalytic hydrogenation of tetraphenylmethane, is analyzed. The Cahn-Ingold-Prelog conformational descriptors of the ideal conformers of tetrasubstituted methanes are reevaluated and an alternative method presented. Methane 2 exists in the crystal in a (g/a/-g) conformation (of approximate S4 symmetry) in which all the rings are in a chair arrangement and are skewed from their perfectly staggered D2d conformation. Molecular mechanics (MM) calculations indicate that the crystallographic conformation is the lowest energy form. Analysis of the 1H and 13C NMR data indicates that, even at low temperatures, the molecule undergoes a fast rotational process which exchanges the ortho and meta groups. On the basis of the MM calculations it is concluded that the preferred rotational pathway involves libration of the four rings via a transition state of D2d symmetry in which all the rings are perfectly staggered.

Original languageAmerican English
Pages (from-to)8132-8138
Number of pages7
JournalJournal of Organic Chemistry
Volume59
Issue number26
DOIs
StatePublished - 1 Dec 1994

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