The preferred conformation of N-β-fluoroethylamides.Observation of the fluorine amide gauche effect

David O'Hagan, C Bilton, JAK Howard, L Knight, DJ Tozer

Research output: Contribution to journalArticlepeer-review

74 Citations (Scopus)

Abstract

Experimental and theoretical data indicate a preferred conformation for N-beta-fluoroethylamides in which the C-F and C-N(CO) bonds are gauche rather than anti to each other. Theoretical calculations on a model system predict the gauche conformation to be 1.8 kcal mol(-1) lower in energy than the anti conformation. This compares with a value of 0.7 kcal mol(-1) for the gauche effect in 1,2-difluoroethane.

Original languageEnglish
Pages (from-to)605-607
Number of pages3
JournalJournal of Chemical Society, Perkin Transactions 2
Issue number4
DOIs
Publication statusPublished - 2000

Keywords

  • 1,2-DIFLUOROETHANE

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