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Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate

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Title Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate
 
Creator MONDAL, BIPLAB
LAHIRI, GOUTAM KUMAR
NAUMOV, PANCE
SEIK WENG NG
 
Subject ion exchange
crystal structure
hydrogen bonds
organic compounds
 
Description 5-Nitro-2-hydroxybenzaldehyde condenses with benzylamine to yield a Schiff base that exists in the solid state as zwitterionic form as 2-benzyliminiomethylene-4-nitrophenolate. In the crystal structure, two zwitterions are linked together as a centrosymmetric dimer by hydrogen bonds involving the iminium hydrogen atom [N···Ointramonomer=2.653(2), N···Ointradimer=2.880(2) Å]. Geometry-optimizations on the monomeric zwitterion and the isomeric hypothetical 2-benzyliminomethylene-4-nitrophenol molecule by the B3LYP/6-31++G(d,p) method imply an endothermic process [ΔH=12.4 kcal mol−1] for the transfer of the phenolic proton in the hypothetical neutral molecule to furnish the zwitterionic molecule.
 
Publisher Elsevier
 
Date 2009-03-23T05:13:25Z
2011-11-25T20:10:57Z
2011-12-26T13:08:10Z
2011-12-27T05:56:11Z
2009-03-23T05:13:25Z
2011-11-25T20:10:57Z
2011-12-26T13:08:10Z
2011-12-27T05:56:11Z
2002
 
Type Article
 
Identifier Journal of Molecular Structure 613(1-3), 131-135
0022-2860
http://dx.doi.org/10.1016/S0022-2860(02)00132-1
http://hdl.handle.net/10054/1069
http://dspace.library.iitb.ac.in/xmlui/handle/10054/1069
 
Language en