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

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

Research output: Contribution to journalArticle

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) 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 languageEnglish (US)
Pages (from-to)131-135
Number of pages5
JournalJournal of Molecular Structure
Volume613
Issue number1-3
DOIs
StatePublished - Aug 1 2002

Fingerprint

Hydrogen
zwitterions
Crystal structure
crystal structure
Molecules
optimization
Schiff Bases
Geometry
geometry
Protons
molecules
Dimers
imines
hydrogen atoms
Hydrogen bonds
dimers
hydrogen bonds
solid state
Atoms
protons

Keywords

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

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate. / Mondal, Biplab; Lahiri, Goutam Kumar; Naumov, Pance; Ng, Seik Weng.

In: Journal of Molecular Structure, Vol. 613, No. 1-3, 01.08.2002, p. 131-135.

Research output: Contribution to journalArticle

Mondal, Biplab ; Lahiri, Goutam Kumar ; Naumov, Pance ; Ng, Seik Weng. / Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate. In: Journal of Molecular Structure. 2002 ; Vol. 613, No. 1-3. pp. 131-135.
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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.

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