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Paradigms and paradoxes: O- and N-protonated amides, stabilization energy, and resonance energy

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Abstract

Protonation of amides most often occurs on oxygen, unless the amide bond is twisted out of planarity allowing the more favored nitrogen protonation to occur. Protonation of oxygen is believed to take place over that of nitrogen due to increased resonance stabilization of the O-protonated species. Resonance energies for O- and N-protonated dimethylacetamide are quantitated using quantum chemically calculated proton affinities for the two sites.

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Authors and Affiliations

  1. Department of Chemistry, University of New Hampshire, Durham, NH, 03824, USA

    Jessica Morgan & Arthur Greenberg

  2. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD, 21250, USA

    Joel F. Liebman

Authors
  1. Jessica Morgan
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  2. Arthur Greenberg
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  3. Joel F. Liebman
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Correspondence to Joel F. Liebman.

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Morgan, J., Greenberg, A. & Liebman, J.F. Paradigms and paradoxes: O- and N-protonated amides, stabilization energy, and resonance energy. Struct Chem 23, 197–199 (2012). https://doi.org/10.1007/s11224-011-9851-7

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  • DOI: https://doi.org/10.1007/s11224-011-9851-7

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