Structures and energetics of two bridgehead lactams and their N- and O-protonated forms: An ab initio molecular orbital study

Document Type

Article

Publication Date

1-1-1993

Abstract

Ab initio molecular orbital calculations optimized with the 6-31G* basis set were employed to investigate the structures, resonance energies, and protonation sites of the two bridgehead bicyclic lactams 1-azabicyclo[2.2.2]-octan-2-one (2-quinuclidone) and 1-azabicyclo[3.3.1]nonan-2-one. The structures and resonance energies reflect the absence of resonance stabilization in the first molecule and somewhat reduced resonance in the second molecule. While planar amides protonate on oxygen, 2-quinuclidone very strongly favors N-protonation while the N- and O-protonated forms in the 3.3.1 system are almost equal in energy. Discussion of structures and energies is given in the context of resonance theory.

Identifier

12044251219 (Scopus)

Publication Title

Journal of the American Chemical Society

ISSN

00027863

First Page

6958

Last Page

6961

Issue

15

Volume

115

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