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

doi:10.1039/C39760000399

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-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 language	English
Pages (from-to)	399-400
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	11
DOIs	https://doi.org/10.1039/C39760000399
Publication status	Published - 1 Dec 1976

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title = "The conformational analysis of saturated heterocycles. N-inversion in hindered piperidines",

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.",

author = "Anet, {Frank A.L.} and Issa Yavari and Ferguson, {Ian J.} and Katritzky, {Alan R.} and Marcial Moreno-Ma{\~n}as and Robinson, {Michael J.T.}",

year = "1976",

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The conformational analysis of saturated heterocycles. N-inversion in hindered piperidines. / Anet, Frank A.L.; Yavari, Issa; Ferguson, Ian J.; Katritzky, Alan R.; Moreno-Mañas, Marcial; Robinson, Michael J.T.

In: Journal of the Chemical Society, Chemical Communications, No. 11, 01.12.1976, p. 399-400.

Research output: Contribution to journal › Article › Research › peer-review

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AU - Moreno-Mañas, Marcial

AU - Robinson, Michael J.T.

PY - 1976/12/1

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N2 - 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.

AB - 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.

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