Volume 59, Issue 10 pp. o596-o597

2-Bromo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, a new unexpected bifunctional building block for combinatorial chemistry

Jana Sopková-de Oliveira Santos

Jana Sopková-de Oliveira Santos

Centre d'Études et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen, 5 rue Vaubénard, 14032 Caen, France

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Alexandre Bouillon

Alexandre Bouillon

Centre d'Études et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen, 5 rue Vaubénard, 14032 Caen, France

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Jean-Charles Lancelot

Jean-Charles Lancelot

Centre d'Études et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen, 5 rue Vaubénard, 14032 Caen, France

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Sylvain Rault

Sylvain Rault

Centre d'Études et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen, 5 rue Vaubénard, 14032 Caen, France

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First published: 09 June 2004
Jana Sopková-de Oliveira Santos, e-mail: [email protected]

Abstract

The first reported structure of a pyridin-2-ylboron derivative, viz. the title compound, C11H15BBrNO2, (I), is compared with its regioisomer 2-bromo-5-(4,4,5,5-tetra­methyl-1,3,2-dioxa­borolan-2-yl)­pyridine, (II) [Sopková-de Oliveira Santos, Lancelot, Bouillon & Rault (2003). Acta Cryst. C59, o111o113]. Structural differences are observed, firstly in the orientation of the dioxaborolane ring with respect to the pyridine ring and secondly in the bond angles of the BO2 group. These differences do not explain the experimentally observed differences in chemical reactivity between (I) and (II) but do confirm the relatively lower stability of (I). However, ab initio calculations of the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital), based on the known crystal structures of the two compounds, show different distributions, which correspond to the differences observed during chemical reactions.

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