Dynamics of internal rotation in 2-(cycloalkenyl)ethyl radicals

John C. Walton*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

2-(Cycloalkenyl)ethyl radicals having C4 to C7 rings were observed by e.s.r. spectroscopy. The barriers to rotation about the Ċα-Cβ bonds were determined from the temperature variation of the β-hydrogen hyperfine splittings and shown to decrease with increasing ring size. In ail cases, the preferred conformation about the Cβ-Cγ bond was found to be the one in which the Ċα-Cβ bond makes an angle of 90° with the plane of the ring. Exchange broadening due to restricted rotation about the Cβ-Cγ bond was observed and the rotation barriers were determined for the radicals with C6 and C7 rings. The radicals were studied using the semi-empirical MINDO/3 and MNDO methods and the corresponding hydrocarbons were investigated by the MM2 force field approach. The variations in the rotational barrier heights were attributed to steric effects.

Original languageEnglish
Pages (from-to)1809-1813
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number12
Publication statusPublished - 1 Dec 1987

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