Unimolecular Rearrangements of Carbanions in the Gas Phase. 2. Cyclopropyl Anions

Phillip K. Chou, Gregg D. Dahlke, Steven R Kass

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

We have examined the gas-phase unimolecular rearrangements of a series of substituted cyclopropyl anions ([formula omitted], and CN; X = Y = CO2CH3) with a variable temperature flowing afterglow device. The ring opening barriers range from 19 to ≥36 kcal mol−1 and are well reproduced by ab initio molecular orbital calculations. An analysis of eight monosubstituted cyclopropyl anions reveals that the flexibility (ease of inversion) and thermodynamic stability of these ions account for their tendency to isomerize.

Original languageEnglish (US)
Pages (from-to)315-324
Number of pages10
JournalJournal of the American Chemical Society
Volume115
Issue number1
DOIs
StatePublished - Jan 1 1993

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