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, Kazomu
AU - Ishida, Hiroyuki
AU - Fejfarova, Karla
AU - Dusek, Michal
N1 - Funding Information:
We acknowledge Golestan University (GU) for partial support of this work, Okayama University (OU) and the project Praemium Academiae of the Academy of Sciences (ASCR).
Publisher Copyright:
© 2013
PY - 2017/5
Y1 - 2017/5
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
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U2 - 10.1016/j.arabjc.2013.07.007
DO - 10.1016/j.arabjc.2013.07.007
M3 - Article
AN - SCOPUS:84882763714
SN - 1878-5352
VL - 10
SP - S1808-S1813
JO - Arabian Journal of Chemistry
JF - Arabian Journal of Chemistry
ER -