Ring inversion in cyclohexane: a textbook example

ABSTRACT

The ring inversion of cyclohexane is a classic textbook example in organic chemistry of large-scale intramolecular interconversion. Early work by Luz using deuterated cyclohexane has shown how the interconversion rate can be studied. Here the complex proton NMR spectrum of cyclohexane is reported. We apply liquid-crystal ¹H NMR spectroscopy as a function of temperature to study the interconversion rate process. For low temperatures interconversion is slow, at higher temperatures the fast interconversion limit is approached. For intermediate temperatures significant line broadening is observed as the signature of the interconversion process.

Graphical Abstract

KEYWORDS:

• NMR
• cyclohexane
• interconversion
• conformation
• evolutionary algorithms
• liquid crystal
• orientational order

Disclosure statement

No potential conflict of interest was reported by the authors.

Dedication

We dedicate this paper to the late Zeev Luz, an outstanding scientist and an outstanding person. We acknowledge several stimulating conversations with Zeev about this project.