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

Biplab Mondal; Goutam Kumar Lahiri; Panče Naumov; Seik Weng Ng

doi:10.1016/S0022-2860(02)00132-1

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

Biplab Mondal, Goutam Kumar Lahiri, Panče Naumov, Seik Weng Ng

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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···O_intramonomer = 2.653(2), N···O_intradimer = 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.

Original language	English (US)
Pages (from-to)	131-135
Number of pages	5
Journal	Journal of Molecular Structure
Volume	613
Issue number	1-3
DOIs	https://doi.org/10.1016/S0022-2860(02)00132-1
State	Published - Aug 1 2002

Keywords

2-Benzyliminiomethylene-4-nitrophenolate
Crystal structure
Geometry-optimization
Hydrogen bonding
Zwitterion

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

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@article{d1ebf3e893a04a30af15e6bee3fbcba7,

title = "Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate",

abstract = "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) {\AA}]. 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.",

keywords = "2-Benzyliminiomethylene-4-nitrophenolate, Crystal structure, Geometry-optimization, Hydrogen bonding, Zwitterion",

author = "Biplab Mondal and Lahiri, {Goutam Kumar} and Pan{\v c}e Naumov and Ng, {Seik Weng}",

note = "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. ",

year = "2002",

month = aug,

day = "1",

doi = "10.1016/S0022-2860(02)00132-1",

language = "English (US)",

volume = "613",

pages = "131--135",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier",

number = "1-3",

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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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