Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

9-2009

Journal or Book Title

Journal of the American Chemical Society

Volume

131

Issue

40

First Page

14243

Last Page

14245

DOI

10.1021/ja9054965

Abstract

Attractive interactions between two carboxamide groups in a “stacked” geometry are explored under isolated molecule conditions. Infrared spectra of single conformations of a small γ-peptide, Ac-γ2-hPhe-NHMe, reveal the presence of a conformation in which the two amide planes are approximately parallel with the amide dipoles in an antialigned orientation. This stacked conformation is energetically comparable to conformations that contain an intramolecular amide−amide H-bond. Amide stacking interactions can compete with H-bonding in circumstances where the amide groups can be brought into a stacking configuration with minimal strain, opening the way for its use in the design of future foldamer structures.

Comments

Reprinted (adapted) with permission from Journal of the American Chemical Society 131 (2009): 14243, doi:10.1021/ja9054965. Copyright 2009 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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