On the nature of the perfluoroalkyl (Rf) effect

Document Type

Article

Publication Date

1-1-1980

Abstract

In this paper, we assess the ability of trifluoro-methyl groups to thermodynamically stabilize unsaturated and strained organic species relative to saturated analogues. Theoretical calculations with the STO-3G basis set are utilized in this analysis. The resulting theoretical data, as well as experimental calorimetric data, indicate little stabilization and perhaps some destabilization resulting from the replacement of H by CF3 (CF3 is unambiguously less stabilizing than methyl). This substituent effect is readily explained by dominance in CF3-substituted compounds of an electron-withdrawing inductive effect which destabilizes the unsaturated linkages. We thus conclude that the striking thermal stability of perfluoroalkylated strained rings is completely kinetic in nature. The origins of the kinetic effect are explored. © 1980.

Identifier

0001361319 (Scopus)

Publication Title

Tetrahedron

External Full Text Location

https://doi.org/10.1016/0040-4020(80)87012-8

ISSN

00404020

First Page

1161

Last Page

1166

Issue

9

Volume

36

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