European Journal of Chemistry 2019, 10(2), 139-145 | doi: https://doi.org/10.5155/eurjchem.10.2.139-145.1838 | Get rights and content






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Correlation between single crystal data and molecular mechanics calculation of 3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one


Adel Sayed Orabi (1) orcid , Sahar Said El-Sakka (2,*) orcid

(1) Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, Egypt
(2) Chemistry Department, Faculty of Science, Suez University, Suez 43527, Egypt
(*) Corresponding Author

Received: 28 Feb 2019 | Revised: 24 Mar 2019 | Accepted: 29 Mar 2019 | Published: 30 Jun 2019 | Issue Date: June 2019

Abstract


The Schiff base 3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one (L), was prepared and characterized by elemental analysis, IR, 1H NMR and mass spectral techniques. The crystal and molecular structures were determined by using the single crystal X-ray diffraction data. The crystal was triclinic with unit-cell dimensions: a = 9.051(3) Å, b = 10.245(3) Å, c = 11.016(3) Å, α = 69.28(2)°, β = 81.66(2)°, γ = 64.25(2)°, space group is Pī and Z = 2. The structure was refined by least squares method. The single crystal was prepared by supersaturating method using tetramethoxysilane as gelling agent. Energy minimization for locating stable conformations and single point energy calculations for comparing the obtained and calculated conformations of the same molecule were carried out using molecular mechanics method (MM2 force field). The bond lengths and the bond angles were calculated and compared with the values obtained from the single crystal analysis. The obtained results were discussed and evaluated. Generally, the calculated parameters are in good agreement with the corresponding X-ray diffraction values. The obtained results reveal that, the amine-imine tautomerism is more preferable than keto-enol form and the intra-hydrogen bond stabilize the amine-imine tautomerism.

 


Keywords


Schiff base; Single crystal; Steric energy; Molecular modeling; Diphenylpropanone; Molecular mechanics

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DOI: 10.5155/eurjchem.10.2.139-145.1838

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Orabi, A.; El-Sakka, S. Eur. J. Chem. 2019, 10(2), 139-145. doi:10.5155/eurjchem.10.2.139-145.1838
Orabi, A.; El-Sakka, S. Correlation between single crystal data and molecular mechanics calculation of 3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one. Eur. J. Chem. 2019, 10(2), 139-145. doi:10.5155/eurjchem.10.2.139-145.1838
Orabi, A., & El-Sakka, S. (2019). Correlation between single crystal data and molecular mechanics calculation of 3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one. European Journal of Chemistry, 10(2), 139-145. doi:10.5155/eurjchem.10.2.139-145.1838
Orabi, Adel, & Sahar Said El-Sakka. "Correlation between single crystal data and molecular mechanics calculation of 3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one." European Journal of Chemistry [Online], 10.2 (2019): 139-145. Web. 1 Dec. 2020
Orabi, Adel, AND El-Sakka, Sahar. "Correlation between single crystal data and molecular mechanics calculation of 3-(2-hydroxy-phenylimino)-1,3-diphenyl-propan-1-one" European Journal of Chemistry [Online], Volume 10 Number 2 (30 June 2019)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


DOI Link: https://doi.org/10.5155/eurjchem.10.2.139-145.1838

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