Synthesis, characterization, crystal structure and theoretical studies on 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol

Aliakbar Dehno Khalaji, Hossein Mighani, Milad Kazemnejadi, Kazuma Gotoh, Hiroyuki Ishida, Karla Fejfarova, Michal Dusek

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The Schiff base compound, 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol, has been synthesized by a reaction of 5-bromosalicylaldehyde with 6-methyl-2-aminopyridine and characterized by elemental analyses, 1H-NMR spectroscopy and X-ray single-crystal diffraction. The title compound crystallizes in monoclinic system, space group P21/c, with a = 13.2721(12) Å, b = 4.5481(4) Ǻ, c = 19.972 (2) Ǻ, β = 96.653 (3)°, V = 1197.4 (2) Ǻ3 and Z = 4. The molecular geometry obtained from X-ray crystallography has been compared with that of the title compound in the ground state calculated by using the density function method (B3LYP) with 6/31G basis set. Calculated results show that DFT can well reproduce the structure of the title compound. The DFT results show that the molecule exists only in enol form. The molecular conformation of the title compound is stabilized by an intramolecular O1-H1·N1 hydrogen bond.

Original languageEnglish
JournalArabian Journal of Chemistry
DOIs
Publication statusAccepted/In press - 2013

Fingerprint

Phenol
Discrete Fourier transforms
Phenols
Crystal structure
Schiff Bases
X ray crystallography
Probability density function
Ground state
Nuclear magnetic resonance spectroscopy
Conformations
Hydrogen bonds
Diffraction
Single crystals
X rays
Molecules
Geometry
alpha-aminopyridine
5-bromosalicylaldehyde

Keywords

  • DFT
  • Hydrogen bond
  • Schiff base
  • Single-crystal
  • Spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Synthesis, characterization, crystal structure and theoretical studies on 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol. / Khalaji, Aliakbar Dehno; Mighani, Hossein; Kazemnejadi, Milad; Gotoh, Kazuma; Ishida, Hiroyuki; Fejfarova, Karla; Dusek, Michal.

In: Arabian Journal of Chemistry, 2013.

Research output: Contribution to journalArticle

@article{822938d910e6490dab0ecaeef77870e7,
title = "Synthesis, characterization, crystal structure and theoretical studies on 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol",
abstract = "The Schiff base compound, 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol, has been synthesized by a reaction of 5-bromosalicylaldehyde with 6-methyl-2-aminopyridine and characterized by elemental analyses, 1H-NMR spectroscopy and X-ray single-crystal diffraction. The title compound crystallizes in monoclinic system, space group P21/c, with a = 13.2721(12) {\AA}, b = 4.5481(4) Ǻ, c = 19.972 (2) Ǻ, β = 96.653 (3)°, V = 1197.4 (2) Ǻ3 and Z = 4. The molecular geometry obtained from X-ray crystallography has been compared with that of the title compound in the ground state calculated by using the density function method (B3LYP) with 6/31G basis set. Calculated results show that DFT can well reproduce the structure of the title compound. The DFT results show that the molecule exists only in enol form. The molecular conformation of the title compound is stabilized by an intramolecular O1-H1·N1 hydrogen bond.",
keywords = "DFT, Hydrogen bond, Schiff base, Single-crystal, Spectroscopy",
author = "Khalaji, {Aliakbar Dehno} and Hossein Mighani and Milad Kazemnejadi and Kazuma Gotoh and Hiroyuki Ishida and Karla Fejfarova and Michal Dusek",
year = "2013",
doi = "10.1016/j.arabjc.2013.07.007",
language = "English",
journal = "Arabian Journal of Chemistry",
issn = "1878-5352",
publisher = "King Saud University",

}

TY - JOUR

T1 - Synthesis, characterization, crystal structure and theoretical studies on 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol

AU - Khalaji, Aliakbar Dehno

AU - Mighani, Hossein

AU - Kazemnejadi, Milad

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

AU - Fejfarova, Karla

AU - Dusek, Michal

PY - 2013

Y1 - 2013

N2 - The Schiff base compound, 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol, has been synthesized by a reaction of 5-bromosalicylaldehyde with 6-methyl-2-aminopyridine and characterized by elemental analyses, 1H-NMR spectroscopy and X-ray single-crystal diffraction. The title compound crystallizes in monoclinic system, space group P21/c, with a = 13.2721(12) Å, b = 4.5481(4) Ǻ, c = 19.972 (2) Ǻ, β = 96.653 (3)°, V = 1197.4 (2) Ǻ3 and Z = 4. The molecular geometry obtained from X-ray crystallography has been compared with that of the title compound in the ground state calculated by using the density function method (B3LYP) with 6/31G basis set. Calculated results show that DFT can well reproduce the structure of the title compound. The DFT results show that the molecule exists only in enol form. The molecular conformation of the title compound is stabilized by an intramolecular O1-H1·N1 hydrogen bond.

AB - The Schiff base compound, 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol, has been synthesized by a reaction of 5-bromosalicylaldehyde with 6-methyl-2-aminopyridine and characterized by elemental analyses, 1H-NMR spectroscopy and X-ray single-crystal diffraction. The title compound crystallizes in monoclinic system, space group P21/c, with a = 13.2721(12) Å, b = 4.5481(4) Ǻ, c = 19.972 (2) Ǻ, β = 96.653 (3)°, V = 1197.4 (2) Ǻ3 and Z = 4. The molecular geometry obtained from X-ray crystallography has been compared with that of the title compound in the ground state calculated by using the density function method (B3LYP) with 6/31G basis set. Calculated results show that DFT can well reproduce the structure of the title compound. The DFT results show that the molecule exists only in enol form. The molecular conformation of the title compound is stabilized by an intramolecular O1-H1·N1 hydrogen bond.

KW - DFT

KW - Hydrogen bond

KW - Schiff base

KW - Single-crystal

KW - Spectroscopy

UR - http://www.scopus.com/inward/record.url?scp=84882763714&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84882763714&partnerID=8YFLogxK

U2 - 10.1016/j.arabjc.2013.07.007

DO - 10.1016/j.arabjc.2013.07.007

M3 - Article

AN - SCOPUS:84882763714

JO - Arabian Journal of Chemistry

JF - Arabian Journal of Chemistry

SN - 1878-5352

ER -