The conformational analysis of saturated heterocycles. N-inversion in hindered piperidines

Frank A.L. Anet, Issa Yavari, Ian J. Ferguson, Alan R. Katritzky, Marcial Moreno-Mañas, Michael J.T. Robinson

Research output: Contribution to journalArticleResearchpeer-review

57 Citations (Scopus)

Abstract

Results from a new dynamic n.m.r. method, applicable to heavily biased equilibria, and kinetically controlled protonation studies agree when applied to 1,2,2,6-tetramethylpiperidine, giving the free energy difference for N-inversion [ΔG° (1E → 1A)] as 1-9 ± 0·2 at 213 K (d.n.m.r.) and 1·95 ± 0·1 kcal mol-1 at 293 and 373 K (kinetic protonation); the free energy of activation [ΔG ‡(1E → 1A)] is 11·0 ± 0·3 kcal mol-1 at 213 K.
Original languageEnglish
Pages (from-to)399-400
JournalJournal of the Chemical Society, Chemical Communications
Issue number11
DOIs
Publication statusPublished - 1 Dec 1976

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