Synthesis and Crystal Structure of a Ternary Lattice Inclusion System of C-4-acetamidophenylcalix[4]-2-methylresorcinarene dimethylsulfoxide tetrasolvate dihydrate

Hamza M. Abosadiya, Siti Aishah Hasbullah, Jumina, Bohari M. Yamin

Research output: Contribution to journalArticle

Abstract

C-4-acetamidophenylcalix[4]-2-methylresorcinarene was synthesized by condensation reaction of 2-methylresorcinol with 4-acetamidobenzaldehyde in the presence of concentrated HCl. The compound was characterized by infrared (IR), 1H, and 13C NMR spectroscopy. Single crystal X-ray analysis revealed that the molecule crystallized in a triclinic crystal system with space group of Pī and the unit cell dimensions are a = 8.929(1)Å, b = 13.804(2)Å, c = 14.471(2)Å, α = 76.766(4)°, β = 78.563(4)°, γ = 87.168(4)°, Z = 1, and V = 1702.0(4)Å3. The calix molecule is associated with four dimethylsulfoxide (DMSO) and two water molecules of crystallization that contribute to the stability of the solid via hydrogen bonding. The supramolecule adopts a chair (C2h ) conformation with four phenyl linkage groups that are in rctt (cis-trans-trans) configuration isomer. The thermal gravimetric investigation showed three mass loss steps that occurred at about 100, 400, and 900°C, respectively. The compound formed after the first loss is thermally stable in the range of 100-400°C after which the calix moiety began to decompose.

Original languageEnglish
JournalBulletin of the Korean Chemical Society
DOIs
Publication statusAccepted/In press - 2015

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Dimethyl Sulfoxide
Crystal lattices
Crystal structure
Molecules
Condensation reactions
X ray analysis
Crystallization
Isomers
Nuclear magnetic resonance spectroscopy
Conformations
Hydrogen bonds
Single crystals
Infrared radiation
Crystals
Water

Keywords

  • Calix[4]resorcinarenes
  • Hydrogen bonds
  • Synthesis
  • Thermal gravimetric study
  • X-ray structural

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Synthesis and Crystal Structure of a Ternary Lattice Inclusion System of C-4-acetamidophenylcalix[4]-2-methylresorcinarene dimethylsulfoxide tetrasolvate dihydrate",
abstract = "C-4-acetamidophenylcalix[4]-2-methylresorcinarene was synthesized by condensation reaction of 2-methylresorcinol with 4-acetamidobenzaldehyde in the presence of concentrated HCl. The compound was characterized by infrared (IR), 1H, and 13C NMR spectroscopy. Single crystal X-ray analysis revealed that the molecule crystallized in a triclinic crystal system with space group of Pī and the unit cell dimensions are a = 8.929(1){\AA}, b = 13.804(2){\AA}, c = 14.471(2){\AA}, α = 76.766(4)°, β = 78.563(4)°, γ = 87.168(4)°, Z = 1, and V = 1702.0(4){\AA}3. The calix molecule is associated with four dimethylsulfoxide (DMSO) and two water molecules of crystallization that contribute to the stability of the solid via hydrogen bonding. The supramolecule adopts a chair (C2h ) conformation with four phenyl linkage groups that are in rctt (cis-trans-trans) configuration isomer. The thermal gravimetric investigation showed three mass loss steps that occurred at about 100, 400, and 900°C, respectively. The compound formed after the first loss is thermally stable in the range of 100-400°C after which the calix moiety began to decompose.",
keywords = "Calix[4]resorcinarenes, Hydrogen bonds, Synthesis, Thermal gravimetric study, X-ray structural",
author = "Abosadiya, {Hamza M.} and Hasbullah, {Siti Aishah} and Jumina and Yamin, {Bohari M.}",
year = "2015",
doi = "10.1002/bkcs.10597",
language = "English",
journal = "Bulletin of the Korean Chemical Society",
issn = "0253-2964",
publisher = "Korean Chemical Society",

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TY - JOUR

T1 - Synthesis and Crystal Structure of a Ternary Lattice Inclusion System of C-4-acetamidophenylcalix[4]-2-methylresorcinarene dimethylsulfoxide tetrasolvate dihydrate

AU - Abosadiya, Hamza M.

AU - Hasbullah, Siti Aishah

AU - Jumina,

AU - Yamin, Bohari M.

PY - 2015

Y1 - 2015

N2 - C-4-acetamidophenylcalix[4]-2-methylresorcinarene was synthesized by condensation reaction of 2-methylresorcinol with 4-acetamidobenzaldehyde in the presence of concentrated HCl. The compound was characterized by infrared (IR), 1H, and 13C NMR spectroscopy. Single crystal X-ray analysis revealed that the molecule crystallized in a triclinic crystal system with space group of Pī and the unit cell dimensions are a = 8.929(1)Å, b = 13.804(2)Å, c = 14.471(2)Å, α = 76.766(4)°, β = 78.563(4)°, γ = 87.168(4)°, Z = 1, and V = 1702.0(4)Å3. The calix molecule is associated with four dimethylsulfoxide (DMSO) and two water molecules of crystallization that contribute to the stability of the solid via hydrogen bonding. The supramolecule adopts a chair (C2h ) conformation with four phenyl linkage groups that are in rctt (cis-trans-trans) configuration isomer. The thermal gravimetric investigation showed three mass loss steps that occurred at about 100, 400, and 900°C, respectively. The compound formed after the first loss is thermally stable in the range of 100-400°C after which the calix moiety began to decompose.

AB - C-4-acetamidophenylcalix[4]-2-methylresorcinarene was synthesized by condensation reaction of 2-methylresorcinol with 4-acetamidobenzaldehyde in the presence of concentrated HCl. The compound was characterized by infrared (IR), 1H, and 13C NMR spectroscopy. Single crystal X-ray analysis revealed that the molecule crystallized in a triclinic crystal system with space group of Pī and the unit cell dimensions are a = 8.929(1)Å, b = 13.804(2)Å, c = 14.471(2)Å, α = 76.766(4)°, β = 78.563(4)°, γ = 87.168(4)°, Z = 1, and V = 1702.0(4)Å3. The calix molecule is associated with four dimethylsulfoxide (DMSO) and two water molecules of crystallization that contribute to the stability of the solid via hydrogen bonding. The supramolecule adopts a chair (C2h ) conformation with four phenyl linkage groups that are in rctt (cis-trans-trans) configuration isomer. The thermal gravimetric investigation showed three mass loss steps that occurred at about 100, 400, and 900°C, respectively. The compound formed after the first loss is thermally stable in the range of 100-400°C after which the calix moiety began to decompose.

KW - Calix[4]resorcinarenes

KW - Hydrogen bonds

KW - Synthesis

KW - Thermal gravimetric study

KW - X-ray structural

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