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

Stephan M Levonis, Brighid B. Pappin, Peter C. Healy, Milton J. Kiefel, Michela Simone, Todd A. Houston

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Abstract

The 5-nitrosalicylate ester of 2-acetamidophenylboronic acid (C 15 H 10 BN 2 O 6) 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.
Original languageEnglish
Pages (from-to)167-169
Number of pages3
JournalHeterocyclic Communications
Volume23
Issue number3
DOIs
Publication statusPublished - 27 Jun 2017
Externally publishedYes

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