- 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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