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Molecules 2015, 20(1), 1686-1711; doi:10.3390/molecules20011686

Hybrids of Salicylalkylamides and Mannich Bases: Control of the Amide Conformation by Hydrogen Bonding in Solution and in the Solid State

1
Institute of Medical Chemistry, Center of Pathobiochemistry and Genetics, Medical University of Vienna, Währingerstrasse 10, Vienna 1090, Austria
2
Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, Vienna 1090, Austria
3
University of Applied Sciences Wiener Neustadt, Konrad-Lorenz-Strasse 10, Tulln a. d. Donau 3430, Austria
4
Structure Analysis Centre, University of Vienna, Währingerstrasse 38, Vienna 1090, Austria
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 27 November 2014 / Revised: 4 January 2015 / Accepted: 12 January 2015 / Published: 20 January 2015
(This article belongs to the Section Medicinal Chemistry)
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Abstract

3-Aminomethylation of salicylalkylamides afforded hybrids with a Mannich base. In addition, it triggered the rotation of the amide bond. The observed conformational switch is driven by strong intramolecular hydrogen bonding between the Mannich base and phenolic group. Crystal structure analysis reveals the stabilization of the hybrid molecules by double hydrogen bonding of the phenolic OH, which acts as an acceptor and donor simultaneously. The molecules contain an amide site and a Mannich base site in an orthogonal spatial arrangement. The intramolecular hydrogen bonds are persistent in a nonpolar solvent (e.g., chloroform). The conformational change can be reversed upon protection or protonation of the Mannich base nitrogen. View Full-Text
Keywords: salicylamide; Mannich base; hybrid; conformation; intramolecular hydrogen bonding; conformational switch salicylamide; Mannich base; hybrid; conformation; intramolecular hydrogen bonding; conformational switch
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Dank, C.; Kirchknopf, B.; Mastalir, M.; Kählig, H.; Felsinger, S.; Roller, A.; Arion, V.B.; Gstach, H. Hybrids of Salicylalkylamides and Mannich Bases: Control of the Amide Conformation by Hydrogen Bonding in Solution and in the Solid State. Molecules 2015, 20, 1686-1711.

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