TY - JOUR
T1 - Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate
AU - Mondal, Biplab
AU - Lahiri, Goutam Kumar
AU - Naumov, Panče
AU - Ng, Seik Weng
N1 - Funding Information:
We thank the National Single-Crystal Diffractometer Facility, Indian Institute of Technology, Bombay for the diffraction measurements, and the Council of Scientific & Industrial Research, New Delhi and the University of Malaya (PJP 0758/2001A) for generously supporting this work.
PY - 2002/8/1
Y1 - 2002/8/1
N2 - 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(12) 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.
AB - 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(12) 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.
KW - 2-Benzyliminiomethylene-4-nitrophenolate
KW - Crystal structure
KW - Geometry-optimization
KW - Hydrogen bonding
KW - Zwitterion
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U2 - 10.1016/S0022-2860(02)00132-1
DO - 10.1016/S0022-2860(02)00132-1
M3 - Article
AN - SCOPUS:0036681446
VL - 613
SP - 131
EP - 135
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
SN - 0022-2860
IS - 1-3
ER -