The zwitterionic structure of 2-hydroxy-4-[(2-hydroxybenzylidene)amino]be nzoic acid

The title compound, C14H11NO4, exists in the solid phase in the zwitterionic form, 2-{[(4-carboxy-3-hydroxyphenyl)iminiumyl]me thyl}phenolate, with the H atom from the phenol group on the 2-hydroxybenzylidene ring transferred to the imine N atom, resulting in a strong intramolecular N-H...O hydrogen...

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Bibliographic Details
Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2013-08, Vol.69 (8), p.934-936
Main Authors: Anderson, ABC Junior, De Carvalho, Gustavo SG, Marques, Lippy F, Correa, Charlane C, Da Silva, Adilson D, Machado, Flavia C
Format: Article
Language:English
Subjects:
Bonding
Chemical bonds
Crystallography
Hydrogen bonds
Imines
Networks
Phenol
Rings (mathematics)
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Summary:The title compound, C14H11NO4, exists in the solid phase in the zwitterionic form, 2-{[(4-carboxy-3-hydroxyphenyl)iminiumyl]me thyl}phenolate, with the H atom from the phenol group on the 2-hydroxybenzylidene ring transferred to the imine N atom, resulting in a strong intramolecular N-H...O hydrogen bond between the iminium H atom and the phenolate O atom, forming a six-membered hydrogen-bonded ring. In addition, there is an intramolecular O-H...O hydrogen bond between the carboxylic acid group and the adjacent hydroxy group of the other ring, and an intermolecular C-H...O contact involving the phenol group and the C-H group adjacent to the imine bond, connecting the molecules into a two-dimensional network in the (10) plane. pi - pi stacking interactions result in a three-dimensional network. This study is important because it provides crystallographic evidence, supported by IR data, for the iminium zwitterionic form of Schiff bases.
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270113018143