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

doi:10.1515/hc-2017-0023

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 language	English
Pages (from-to)	167-169
Number of pages	3
Journal	Heterocyclic Communications
Volume	23
Issue number	3
DOIs	https://doi.org/10.1515/hc-2017-0023
Publication status	Published - 27 Jun 2017
Externally published	Yes

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title = "Crystallization-induced amide bond formation creates a boron-centered spirocyclic system",

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.",

author = "Levonis, {Stephan M} and Pappin, {Brighid B.} and Healy, {Peter C.} and Kiefel, {Milton J.} and Michela Simone and Houston, {Todd A.}",

year = "2017",

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language = "English",

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T1 - Crystallization-induced amide bond formation creates a boron-centered spirocyclic system

AU - Levonis, Stephan M

AU - Pappin, Brighid B.

AU - Healy, Peter C.

AU - Kiefel, Milton J.

AU - Simone, Michela

AU - Houston, Todd A.

PY - 2017/6/27

Y1 - 2017/6/27

N2 - 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.

AB - 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.

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U2 - 10.1515/hc-2017-0023

DO - 10.1515/hc-2017-0023

M3 - Article

SN - 0793-0283

VL - 23

SP - 167

EP - 169

JO - Heterocyclic Communications

JF - Heterocyclic Communications

IS - 3

ER -

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

Abstract

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