Nitrogen inversion barrier of 2-methyl-2-azabicyclo(2.2.1)heptane. The role of torsional strain in pyramidal inversion

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Date: Feb. 23, 1996
From: Journal of Organic Chemistry(Vol. 61, Issue 4)
Publisher: American Chemical Society
Document Type: Article
Length: 82 words

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Abstract :

The dynamic NMR analysis of the 13C spectra of an isomeric bicyclic amine, 2-methyl-2-azabicyclo(2.2.1)heptane, is described. The results showed that the endo isomer of the compound is more stable than the exo isomer by 0.3kcal mol-1. The inversion barrier of 7.2 kcal mol-1 is lower when compared to model acyclic amines although its internal CNC bond angles is less than the tetrahedral angel of 109.47 degrees. Analysis showed the influence of torsional (eclipsing) strain and angle strain in determining the inversion barrier.

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Gale Document Number: GALE|A18349944