Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 6, Pages 3159-3163Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00019
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Funding
- Narodowe Centrum Nauki [2014/15/D/STS/02731]
- Rutgers University
- NSF [CAREER CHE-1650766]
- Wroclaw Center for Networking and Supercomputing [WCSS159]
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Planarity of the amide bond represents one of the most widely recognized properties of amides. Herein, we report a combined structural and computational study on the effect of ortho-substitution on resonance and barriers to rotation in tertiary aromatic amides. We demonstrate that ortho-chloro substitution in a class of benzamides that are important from the reactivity and medicinal chemistry perspective results in increased barriers to rotation around both the N-C(O) and C-C(O) axes. The effect of steric hindrance on structures, resonance energies, barriers to rotation, and proton affinities is discussed. The present study strongly supports the use of ortho-substitution in common benzamides to strengthen amidic resonance.
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