Experimental and theoretical studies of the schiff base (Z)-1-(thiophen-2-yl- methyleneamino) propane-2-ol

Asnake Lealem Berhanu, Neha Sharma, Irshad Mohiuddin, Ashok Kumar Malik, Jatinder Singh Aulakh, Jechan Lee, Ki Hyun Kim

Research output: Contribution to journalArticle

Abstract

In this study, a quantum chemical model was developed to better account for the properties of a Schiff base, (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol, which is derived from thiophene-2-carboxy aldehyde and 1-amino-2-propanol. To predict its molecular structure, the assignment of the vibrational wavelength (for FT-IR) and chemical shift (for 1HNMR) of (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol was performed experimentally and theoretically. All of the theoretical calculations were performed using the Gaussian 09 program package. The theoretically and experimentally obtained results were in good agreement (R2 ≥ 0.99). The energies of the highest occupied and lowest unoccupied molecular orbitals were estimated using B3LYP (Becke three-parameter hybrid functional combined with Lee–Yang–Parr correlation functional)/6-311++G (d, p). Optimization of the structure of (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol provided information concerning the stable form of the geometry of the molecule, stoichiometry of the complexes, and thermodynamic parameters (e.g., energy and entropy). The results indicate that the Schiff base formed stable complexes with Ni2+. The energy of the complex was much lower than that of the free Schiff base. The charge distribution values of each atom in the Schiff base were in agreement with the Pauling scale for electronegativity and vibrational wavelength.

Original languageEnglish
Article number127104
JournalJournal of Molecular Structure
Volume1200
DOIs
StatePublished - 2020 Jan 15

Fingerprint

Propane
Schiff Bases
Thiophenes
Wavelength
Electronegativity
Charge distribution
Chemical shift
Molecular orbitals
Aldehydes
Stoichiometry
Molecular structure
Entropy
Thermodynamics
Atoms
Molecules
Geometry

Keywords

  • DFT calculations
  • HOMO
  • LUMO
  • Schiff base

Cite this

Berhanu, Asnake Lealem ; Sharma, Neha ; Mohiuddin, Irshad ; Malik, Ashok Kumar ; Aulakh, Jatinder Singh ; Lee, Jechan ; Kim, Ki Hyun. / Experimental and theoretical studies of the schiff base (Z)-1-(thiophen-2-yl- methyleneamino) propane-2-ol. In: Journal of Molecular Structure. 2020 ; Vol. 1200.
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Experimental and theoretical studies of the schiff base (Z)-1-(thiophen-2-yl- methyleneamino) propane-2-ol. / Berhanu, Asnake Lealem; Sharma, Neha; Mohiuddin, Irshad; Malik, Ashok Kumar; Aulakh, Jatinder Singh; Lee, Jechan; Kim, Ki Hyun.

In: Journal of Molecular Structure, Vol. 1200, 127104, 15.01.2020.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Experimental and theoretical studies of the schiff base (Z)-1-(thiophen-2-yl- methyleneamino) propane-2-ol

AU - Berhanu, Asnake Lealem

AU - Sharma, Neha

AU - Mohiuddin, Irshad

AU - Malik, Ashok Kumar

AU - Aulakh, Jatinder Singh

AU - Lee, Jechan

AU - Kim, Ki Hyun

PY - 2020/1/15

Y1 - 2020/1/15

N2 - In this study, a quantum chemical model was developed to better account for the properties of a Schiff base, (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol, which is derived from thiophene-2-carboxy aldehyde and 1-amino-2-propanol. To predict its molecular structure, the assignment of the vibrational wavelength (for FT-IR) and chemical shift (for 1HNMR) of (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol was performed experimentally and theoretically. All of the theoretical calculations were performed using the Gaussian 09 program package. The theoretically and experimentally obtained results were in good agreement (R2 ≥ 0.99). The energies of the highest occupied and lowest unoccupied molecular orbitals were estimated using B3LYP (Becke three-parameter hybrid functional combined with Lee–Yang–Parr correlation functional)/6-311++G (d, p). Optimization of the structure of (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol provided information concerning the stable form of the geometry of the molecule, stoichiometry of the complexes, and thermodynamic parameters (e.g., energy and entropy). The results indicate that the Schiff base formed stable complexes with Ni2+. The energy of the complex was much lower than that of the free Schiff base. The charge distribution values of each atom in the Schiff base were in agreement with the Pauling scale for electronegativity and vibrational wavelength.

AB - In this study, a quantum chemical model was developed to better account for the properties of a Schiff base, (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol, which is derived from thiophene-2-carboxy aldehyde and 1-amino-2-propanol. To predict its molecular structure, the assignment of the vibrational wavelength (for FT-IR) and chemical shift (for 1HNMR) of (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol was performed experimentally and theoretically. All of the theoretical calculations were performed using the Gaussian 09 program package. The theoretically and experimentally obtained results were in good agreement (R2 ≥ 0.99). The energies of the highest occupied and lowest unoccupied molecular orbitals were estimated using B3LYP (Becke three-parameter hybrid functional combined with Lee–Yang–Parr correlation functional)/6-311++G (d, p). Optimization of the structure of (Z)-1-(thiophen-2-yl-methyleneamino) propane-2-ol provided information concerning the stable form of the geometry of the molecule, stoichiometry of the complexes, and thermodynamic parameters (e.g., energy and entropy). The results indicate that the Schiff base formed stable complexes with Ni2+. The energy of the complex was much lower than that of the free Schiff base. The charge distribution values of each atom in the Schiff base were in agreement with the Pauling scale for electronegativity and vibrational wavelength.

KW - DFT calculations

KW - HOMO

KW - LUMO

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DO - 10.1016/j.molstruc.2019.127104

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