Crystallization-induced amide bond formation creates a boron-centered spirocyclic system

Title: Crystallization-induced amide bond formation creates a boron-centered spirocyclic system
Creator: Pappin, Brighid B.; Levonis, Stephan M.; Healy, Peter C.; Kiefel, Milton J.; Simone, Michela I.; Houston, Todd A.
Relation: Heterocyclic Communications Vol. 23, Issue 3, p. 167-169
Publisher Link: http://dx.doi.org/10.1515/hc-2017-0023
Publisher: Walter de Gruyter GmbH
Resource Type: journal article
Date: 2017
Description: The 5-nitrosalicylate ester of 2-acetamidophenylboronic acid (C₁₅H₁₀BN₂O₆) is formed under crystallization conditions from the 5-nitrosalicylate ester of 2-aminophenylboronic acid. The boron at the center of this structure exists as a tetrahedral complex produced by a dative bond with the amide carbonyl. The perpendicular shape produces an unusual packing structure including a bifurcated hydrogen bond between the amide hydrogen and carbonyl groups on two neighboring molecules. We propose that this reaction occurs due to increased Lewis acidity of the nitrosalicylate ester of 2-aminophenylboronic acid.
Subject: amidation; boronate ester; crystal structure; dative bond; Lewis acid
Identifier: http://hdl.handle.net/1959.13/1351363
Identifier: uon:30695
Identifier: ISSN:0793-0283
Language: eng
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