Journal
TETRAHEDRON
Volume 68, Issue 19, Pages 3761-3767Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.02.072
Keywords
Boronic acids; Hydrogen bond; B-N bond; Schiff bases; Mannich bases; MP2/6-31+G**; SESE
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Funding
- Ministry of Science and Higher Education [N204 01932/0614]
- X-ray study and Interdisciplinary Centre for Mathematical and Computational Modeling (Warsaw) [120000-501/68-BW-1681/17/05]
- Warsaw University of Technology
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ortho-Iminomethylphenylboronic acids were synthesized from the reaction of 2-formyl-phenylboronic acid with primary aromatic amines. Reduction of these compounds yielded the corresponding aminomethylphenylboronic acids. For both types of the compounds, the crystal structure was determined by single crystal X-ray diffraction method. Hydrogen-bonded dimers with an additional intramolecular B-O-H center dot center dot center dot N hydrogen bond have been observed. Calculations at MP2/6-31+G** level proved that the most stable form is that with the above-mentioned intramolecular hydrogen bond while the form with dative N -> B bond is less favoured. Since the calculated energy difference is small, the competition between possible forms was analyzed in terms of substituent effect stabilization energy (SESE). In the case of p-iminomethylphenylboronic acid, both hydroxyl groups are engaged in intermolecular O-H center dot center dot center dot O interactions resulting in a supramolecular ribbon motif. (C) 2012 Elsevier Ltd. All rights reserved.
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