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Issue 7, 2008
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Supramolecular structures and spontaneous resolution: the case of ortho-substituted phenylboronic acids

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Abstract

The solid state structures of a number of ortho-substituted arylboronic acids, ortho-bromophenyl, ortho-phenylphenyl, pentamethylphenyl, and 10-bromo-9-anthryl, were determined by X-ray diffraction techniques. All boronic acids investigated form dimers in the solid state, but the interconnection of dimers to ribbons differs from that of the parent phenylboronic acid. Pentamethylphenylboronic acid only uses onehydrogen bond but an additional OH–π interaction for connection of dimers, while all others investigated employ two hydrogen bonds for interconnection of dimers to ribbons. 10-Bromo-9-anthrylboronic acid is found to undergo spontaneous resolution of its enantiomers to a racemic conglomerate upon crystallization.

Graphical abstract: Supramolecular structures and spontaneous resolution: the case of ortho-substituted phenylboronic acids

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Article information


Submitted
13 Dec 2007
Accepted
28 Jan 2008
First published
28 Feb 2008

Org. Biomol. Chem., 2008,6, 1201-1207
Article type
Paper

Supramolecular structures and spontaneous resolution: the case of ortho-substituted phenylboronic acids

M. Filthaus, I. M. Oppel and H. F. Bettinger, Org. Biomol. Chem., 2008, 6, 1201
DOI: 10.1039/B719282G

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