European Journal of Chemistry 2019, 10(2), 139-145. doi:10.5155/eurjchem.10.2.139-145.1838

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, Accepted: 29 Mar 2019, Published: 30 Jun 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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.10.2.139-145.1838

Article Metrics


This Abstract was viewed 44 times | PDF Article downloaded 34 times

References

[1]. Delgado, J. N.; Remers W. A., Wilson and Giswold's Textbook of Organic Chemistry Medicinal and Pharmaceutical Chemistry, 10th edition, Lippincott William & Wilkins, 1998.

[2]. Cozzi, P. G. Chem. Soc. Rev. 2004, 33, 410-421.
https://doi.org/10.1039/B307853C

[3]. Kulkarni, A.; Patil, S. A.; Badami, P. S. Eur. J. Med. Chem. 2009, 44, 2904-2912.
https://doi.org/10.1016/j.ejmech.2008.12.012

[4]. Schuetz, S. A.; Silvernail, C. M.; Incarvito, C. D.; Rheingold, A. L.; Clark, J. L.; Day, V. W.; Belot, J. A. Inorg. Chem. 2004, 43, 6203-6214.
https://doi.org/10.1021/ic040006f

[5]. Lentz, A.; Fetzer, T.; Voitenleitner, I.; Hauber, T.; Abou‐El‐Wafa, O. Cryst. Res. Technol. 1990, 25, 391-396.
https://doi.org/10.1002/crat.2170250408

[6]. Martins, F. T.; Legendre, A. O.; Honorato, S. B.; Ayala, A. P.; Doriguetto, A. C.; Ellena, J. Cryst. Growth Des. 2010, 10, 1885-1891.
https://doi.org/10.1021/cg9015959

[7]. Arend, H.; Connelly, J. J. Cryst. Growth. 1982, 56, 642-644.
https://doi.org/10.1016/0022-0248(82)90048-3

[8]. Binzet, G.; Florke, U.; Kulcu, N.; Arslan. H. Eur. J. Chem. 2012, 3, 37-39.
https://doi.org/10.5155/eurjchem.3.1.37-39.591

[9]. Yuanyuan, H.; Fang, B.; Guowei, G.; Jian, M. Eur. J. Chem. 2012, 3, 17-20.
https://doi.org/10.5155/eurjchem.3.1.17-20.534

[10]. El-Shaaer, H. M. Eur. J. Chem. 2012. 3, 51-56.
https://doi.org/10.5155/eurjchem.3.1.51-56.500

[11]. Low, J. N.; Santos, L. M.; Lima, C. F. R. A. C.; Brandao, P.; Gomes, L. R. Eur. J. Chem. 2010, 1, 61-66.
https://doi.org/10.5155/eurjchem.1.2.61-66.76

[12]. Yesilkaynak, T.; Binzet, G.; Emen, F. M.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2010, 1, 1-5.
https://doi.org/10.5155/eurjchem.1.1.1-5.3

[13]. Dudek, M. J.; Ponder, J. W. J. Comput. Chem. 1995, 16, 791-816.
https://doi.org/10.1002/jcc.540160702

[14]. Allinger, N. L.; Burkert, U. Molecular Mechanics. Washington, DC, ACS, USA, 1982.

[15]. Clark, T., A handbook of computational chemistry: A practical guide to chemical structure and energy calculations. Wiley-Interscience, New York, USA, 1985.

[16]. Sheldrick, G. M. Acta Crystallog. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[17]. Ibrahim, E.; Sallam, S.; Orabi, A. S.; El-Shetary, B. A.; Lentz, A. Monatsh. Chemie. 1998, 129, 159-171.
https://doi.org/10.1007/PL00010152

[18]. Henisch, H. K., Crystal growth in gels. Dover Publications, 1996.

[19]. Domagala, S.; Munshi, P.; Ahmed, M.; Guillot, B.; Jelsch, C. Acta Crystallogr. B 2011, 67, 63-78.
https://doi.org/10.1107/S0108768110041996


How to cite


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. 20 Aug. 2019
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)

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

Refbacks

  • There are currently no refbacks.




Copyright (c) 2019 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.