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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Boron
Crystallization
Amides
Esters
Acidity
Hydrogen
Hydrogen bonds
Molecules
Acids
3-aminobenzeneboronic acid

Cite this

Levonis, Stephan M ; Pappin, Brighid B. ; Healy, Peter C. ; Kiefel, Milton J. ; Simone, Michela ; Houston, Todd A. / Crystallization-induced amide bond formation creates a boron-centered spirocyclic system. In: Heterocyclic Communications. 2017 ; Vol. 23, No. 3. pp. 167-169.
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Crystallization-induced amide bond formation creates a boron-centered spirocyclic system. / Levonis, Stephan M; Pappin, Brighid B.; Healy, Peter C.; Kiefel, Milton J.; Simone, Michela; Houston, Todd A.

In: Heterocyclic Communications, Vol. 23, No. 3, 27.06.2017, p. 167-169.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Simone, Michela

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