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

Autor:	Milton J. Kiefel, Todd Ashley Houston, Michela I. Simone, Peter Conrad Healy, Brighid Beatrice Pappin, Stephan M Levonis
Rok vydání:	2017
Předmět:	010405 organic chemistry Organic Chemistry chemistry.chemical_element Crystal structure 010402 general chemistry 01 natural sciences 0104 chemical sciences law.invention Crystallography chemistry law Dipolar bond Peptide bond Lewis acids and bases Crystallization Boron
Zdroj:	Heterocyclic Communications. 23:167-169
ISSN:	2191-0197 0793-0283
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::dd2d54abdaf8a41616ede7597047e3f8 https://doi.org/10.1515/hc-2017-0023 Zobrazit plný text záznamu Plný text ve formátu PDF