Synthesis, spectroscopic characterization, crystal structures, and theoretical studies of (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone

Aliakbar Dehno Khalaji, Gholamhossein Grivani, Samaneh Jalali Akerdi, Kazuma Gotoh, Hiroyuki Ishida, Hossein Mighani

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Two thiosemicarbazones, (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone (24-MBTSC (1)) and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone (25-MBTSC (2)), derived from 2,4-dimethoxybenzaldehyde and 2,5-dimethoxybenzaldehyde, respectively, with thiosemicarbazide have been synthesized and their structures were characterized by elemental analyses, FT-IR, 1H NMR spectroscopy, and X-ray single-crystal diffraction analysis. Molecular orbital calculations have been carried out for 1 and 2 by using an ab initio method (HF) and also density functional method (B3LYP) at 6-31G basis set. Compound 1 crystallizes in the monoclinic system, space group P21/c, with a = 8.1342(5) Å, b = 18.1406(10) Å, c = 8.2847(6) Å, β = 109.7258(17)°, V = 1150.75(12) Å3, and Z = 4, whereas compound 2 crystallizes in the orthorhombic system, space group Pbca, with a = 11.0868(6) Å, b = 13.1332(6) Å, c = 15.9006(8) Å, V = 2315.2(2) Å3, and Z = 8. The compounds 1 and 2 displays a trans-configuration about the C=N double bond.

Original languageEnglish
Pages (from-to)995-1003
Number of pages9
JournalStructural Chemistry
Volume21
Issue number5
DOIs
Publication statusPublished - 2010

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Thiosemicarbazones
Crystal structure
crystal structure
synthesis
Orbital calculations
molecular orbitals
Molecular orbitals
nuclear magnetic resonance
Nuclear magnetic resonance spectroscopy
single crystals
Diffraction
configurations
Display devices
diffraction
Single crystals
spectroscopy
X rays
x rays

Keywords

  • 2,4-Dimethoxybenzaldehyde
  • 2,5-Dimethoxybenzaldehyde
  • Configuration
  • Crystal structure
  • Density functional theory (DFT)
  • HF
  • Thiosemicarbazone

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

Cite this

Synthesis, spectroscopic characterization, crystal structures, and theoretical studies of (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone. / Khalaji, Aliakbar Dehno; Grivani, Gholamhossein; Akerdi, Samaneh Jalali; Gotoh, Kazuma; Ishida, Hiroyuki; Mighani, Hossein.

In: Structural Chemistry, Vol. 21, No. 5, 2010, p. 995-1003.

Research output: Contribution to journalArticle

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title = "Synthesis, spectroscopic characterization, crystal structures, and theoretical studies of (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone",
abstract = "Two thiosemicarbazones, (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone (24-MBTSC (1)) and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone (25-MBTSC (2)), derived from 2,4-dimethoxybenzaldehyde and 2,5-dimethoxybenzaldehyde, respectively, with thiosemicarbazide have been synthesized and their structures were characterized by elemental analyses, FT-IR, 1H NMR spectroscopy, and X-ray single-crystal diffraction analysis. Molecular orbital calculations have been carried out for 1 and 2 by using an ab initio method (HF) and also density functional method (B3LYP) at 6-31G basis set. Compound 1 crystallizes in the monoclinic system, space group P21/c, with a = 8.1342(5) {\AA}, b = 18.1406(10) {\AA}, c = 8.2847(6) {\AA}, β = 109.7258(17)°, V = 1150.75(12) {\AA}3, and Z = 4, whereas compound 2 crystallizes in the orthorhombic system, space group Pbca, with a = 11.0868(6) {\AA}, b = 13.1332(6) {\AA}, c = 15.9006(8) {\AA}, V = 2315.2(2) {\AA}3, and Z = 8. The compounds 1 and 2 displays a trans-configuration about the C=N double bond.",
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T1 - Synthesis, spectroscopic characterization, crystal structures, and theoretical studies of (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone

AU - Khalaji, Aliakbar Dehno

AU - Grivani, Gholamhossein

AU - Akerdi, Samaneh Jalali

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

AU - Mighani, Hossein

PY - 2010

Y1 - 2010

N2 - Two thiosemicarbazones, (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone (24-MBTSC (1)) and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone (25-MBTSC (2)), derived from 2,4-dimethoxybenzaldehyde and 2,5-dimethoxybenzaldehyde, respectively, with thiosemicarbazide have been synthesized and their structures were characterized by elemental analyses, FT-IR, 1H NMR spectroscopy, and X-ray single-crystal diffraction analysis. Molecular orbital calculations have been carried out for 1 and 2 by using an ab initio method (HF) and also density functional method (B3LYP) at 6-31G basis set. Compound 1 crystallizes in the monoclinic system, space group P21/c, with a = 8.1342(5) Å, b = 18.1406(10) Å, c = 8.2847(6) Å, β = 109.7258(17)°, V = 1150.75(12) Å3, and Z = 4, whereas compound 2 crystallizes in the orthorhombic system, space group Pbca, with a = 11.0868(6) Å, b = 13.1332(6) Å, c = 15.9006(8) Å, V = 2315.2(2) Å3, and Z = 8. The compounds 1 and 2 displays a trans-configuration about the C=N double bond.

AB - Two thiosemicarbazones, (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone (24-MBTSC (1)) and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone (25-MBTSC (2)), derived from 2,4-dimethoxybenzaldehyde and 2,5-dimethoxybenzaldehyde, respectively, with thiosemicarbazide have been synthesized and their structures were characterized by elemental analyses, FT-IR, 1H NMR spectroscopy, and X-ray single-crystal diffraction analysis. Molecular orbital calculations have been carried out for 1 and 2 by using an ab initio method (HF) and also density functional method (B3LYP) at 6-31G basis set. Compound 1 crystallizes in the monoclinic system, space group P21/c, with a = 8.1342(5) Å, b = 18.1406(10) Å, c = 8.2847(6) Å, β = 109.7258(17)°, V = 1150.75(12) Å3, and Z = 4, whereas compound 2 crystallizes in the orthorhombic system, space group Pbca, with a = 11.0868(6) Å, b = 13.1332(6) Å, c = 15.9006(8) Å, V = 2315.2(2) Å3, and Z = 8. The compounds 1 and 2 displays a trans-configuration about the C=N double bond.

KW - 2,4-Dimethoxybenzaldehyde

KW - 2,5-Dimethoxybenzaldehyde

KW - Configuration

KW - Crystal structure

KW - Density functional theory (DFT)

KW - HF

KW - Thiosemicarbazone

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U2 - 10.1007/s11224-010-9637-3

DO - 10.1007/s11224-010-9637-3

M3 - Article

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EP - 1003

JO - Structural Chemistry

JF - Structural Chemistry

SN - 1040-0400

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