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Theoretical Study of the N-(2,5-Methylphenyl)salicylaldimine Schiff Base Ligand: Atomic Charges, Molecular Electrostatic Potential, Nonlinear Optical (NLO) Effects and Thermodynamic Properties

  • Zeyrek, Tugrul C.
  • Received : 2013.02.14
  • Accepted : 2013.06.28
  • Published : 2013.08.20

Abstract

Optimized geometrical structure, atomic charges, molecular electrostatic potential, nonlinear optical (NLO) effects and thermodynamic properties of the title compound N-(2,5-methylphenyl)salicylaldimine (I) have been investigated by using ab initio quantum chemical computational studies. Calculated results showed that the enol form of (I) is more stable than keto form. The solvent effect was investigated for obtained molecular energies, hardneses and the atomic charge distributions of (I). Natural bond orbital and frontier molecular orbital analysis of the title compound were also performed. The total molecular dipole moment (${\mu}$), linear polarizability (${\alpha}$), and first-order hyperpolarizability (${\beta}$) were calculated by B3LYP method with 6-31G(d), 6-31+G(d,p), 6-31++G(d,p), 6-311+G(d) and 6-311++G(d,p) basis sets to investigate the NLO properties of the compound (I). The standard thermodynamic functions were obtained for the title compound with the temperature ranging from 200 to 450 K.

Keywords

Density functional theory;Molecular orbitals;Schiff base;Ab initio calculations;Nonlinear optical effects

References

  1. Yang, C. J.; Jenekhe, S. A. Macromolecules 1995, 28, 1180. https://doi.org/10.1021/ma00108a054
  2. Zeyrek, C. T.; Elmali, A.; Elerman, Y. Z. Naturforsch. 2005, 60b, 520.
  3. Larkin, D. R. J. Org. Chem. 1990, 55, 1563. https://doi.org/10.1021/jo00292a035
  4. Vanco, J.; Svajlenova, O.; Racanska, E.; Muselik, J.; Valentova, J. J. Trace Elem. Med. Biol. 2004, 18, 155. https://doi.org/10.1016/j.jtemb.2004.07.003
  5. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626. https://doi.org/10.1021/ja0258226
  6. Ramnauth, R.; Al-Juaid, S.; Motevalli, M.; Parkin, B. C.; Sullivan, A. C. Inorg. Chem. 2004, 43, 4072. https://doi.org/10.1021/ic035318h
  7. Hadjoudis, E.; Vitterakisp, M.; Mavridis, I. M. Tetrahedron 1987, 43, 1345. https://doi.org/10.1016/S0040-4020(01)90255-8
  8. Xu, X. X.; You, X. Z.; Sun, Z. F.; Wang, X.; Liu, H. X. Acta Crystallogr. 1994, C50, 1169.
  9. Durr, H. Angew. Chem. Int. Ed. Engl. 1989, 28, 413. https://doi.org/10.1002/anie.198904131
  10. Dur, H.; Bouas-Laurent, H. Photochromism: Molecules and Systems; Elsevier: Amsterdam, 1990.
  11. Schaumburg, K. et al. In Nanostructure Based on Molecular Materials; Gopel, W., Ziegler, C., Eds.;Willey-VCH: Weinheim, German, 1992.
  12. Ozek, A.; Albayrak, C.; Odabasoglu, M.; Buyukgungor, O. Acta Crystallogr. 2007, C63, 177.
  13. Elmali, A.; Kabak, K.; Kavlakoglu, E.; Elerman, Y.; Durlu, T. N. J. Mol. Struct. 1999, 510, 207. https://doi.org/10.1016/S0022-2860(99)00074-5
  14. Unver, H.; Kabak, M.; Zengin, M.; Durlu, T. N. J. Chem. Crystallogr. 2001, 31, 203. https://doi.org/10.1023/A:1014395132751
  15. Unver, H.; Karakas, A.; Elmali, A. J. Mol. Struct. 2004, 702, 49. https://doi.org/10.1016/j.molstruc.2004.06.008
  16. Emregul, K. C.; Duzgun, E.; Atakol, O. Corros. Sci. 2006, 48, 3243. https://doi.org/10.1016/j.corsci.2005.11.016
  17. Drozdzak, R.; Allaert, B.; Ledoux, N.; Dragutan, I.; Dragutan, V.; Verpoort, R. Coord. Chem. Rev. 2005, 249, 3055. https://doi.org/10.1016/j.ccr.2005.05.003
  18. Karakas, A.; Elmali, A.; Unver, H.; Svoboda, I. J. Mol. Struct. 2004, 702,103. https://doi.org/10.1016/j.molstruc.2004.06.017
  19. Blanchard-Desce, M.; Runser, C.; Fort, A.; Barzoukas, M.; Lehn, J. M.; Bloy, V.; Alain, V. Chem. Phys. 1995, 199, 253. https://doi.org/10.1016/0301-0104(95)00222-A
  20. Sebastian, S.; Sundaraganesan, N.; Karthikeiyan, B.; Srinivasan, V. Spectrochim. Acta, Part A 2001, 78, 590.
  21. Kavitha, E.; Sundaraganesan, N.; Sebastian, S.; Kurt, M. Spectrochim. Acta, Part A 2010, 77, 612. https://doi.org/10.1016/j.saa.2010.06.034
  22. Sun, Y. X.; Hao, Q. L.; Yu, Z.X.; Wei, W. X.; Lu, L. D.; Wang, X. Mol. Phys. 2009, 107, 223. https://doi.org/10.1080/00268970902769471
  23. Seiji, I.; Hiroo, F.; Hidetoshi, K.; Makoto, I.; Nobuaki, K. Bull. Chem. Soc. Jpn. 2003, 76(4), 733. https://doi.org/10.1246/bcsj.76.733
  24. Elmali, A.; Elerman, Y.; Zeyrek, C. T. J. Mol. Struct. 1998, 443, 123. https://doi.org/10.1016/S0022-2860(97)00382-7
  25. Frisch, M. J.; et al. GAUSSIAN 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
  26. Dennington, R.; Keith, T.; Millam, J. GaussView, version 4.1.2; Semichem, Inc.: Shawnee Mission, KS, 2007.
  27. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214. https://doi.org/10.1002/jcc.540030212
  28. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49. https://doi.org/10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO;2-0
  29. Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512. https://doi.org/10.1021/ja00364a005
  30. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 6098.
  31. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, version 3.1; Theoretical Chemistry Institute: University of Wisconsin, Madison, 1995.
  32. Jian, F. F.; Zhao, P. S.; Bai, Z. S.; Zhang, L. Struct. Chem. 2005, 16, 635. https://doi.org/10.1007/s11224-005-8254-z
  33. Ozbek, N.; Kavak, G.; Ozcan, Y.; Ide, S.; Karacan, N. J. Mol. Struct. 2009, 919, 154. https://doi.org/10.1016/j.molstruc.2008.09.010
  34. Geerlings, P.; De Proft, F.; Langenaeker, W. Chem. Rev. 2003, 103, 1793. https://doi.org/10.1021/cr990029p
  35. Pearson, R. G. J. Chem. Ed. 1987, 64, 561. https://doi.org/10.1021/ed064p561
  36. Parr, R. G.; Chattaraj, P. K. J. Am. Chem. Soc. 1991, 113, 1854. https://doi.org/10.1021/ja00005a072
  37. Politzer, P.; Concha, M. C.; Murray, J. S. Int. J. Quantum Chem. 2000, 80, 184. https://doi.org/10.1002/1097-461X(2000)80:2<184::AID-QUA12>3.0.CO;2-O
  38. Schwenke, D. W.; Truhlar, D. H. J. Chem. Phys. 1985, 82, 2418. https://doi.org/10.1063/1.448335
  39. Andraud, C.; Brotin, T.; Garcia, C.; Pelle, F.; Goldner, P.; Bigot, B.; Collet, A. J. Am. Chem. Soc. 1994, 116, 2094. https://doi.org/10.1021/ja00084a055
  40. Thanthiriwatte, K. S.; Nalin de Silva, K. M. J. Mol. Struct. (Theochem) 2002, 617, 169. https://doi.org/10.1016/S0166-1280(02)00419-0
  41. Sun, Y. X.; Hao, Q. L.; Wei, W. X.; Yu, Z. X.; Lu, L. D.; Wang, X.; Wang, Y. S. J. Mol. Struct. 2009, 929, 10. https://doi.org/10.1016/j.molstruc.2009.03.035
  42. Yavuz, M.; Tanak, H. J. Mol. Struct. (Theochem) 2010, 961, 9. https://doi.org/10.1016/j.theochem.2010.08.035
  43. Ruiz Delgado, M. C.; Hernandez, V.; Casado, J.; Lopez Navarre, J. T.; Raimundo, J. M.; Blanchard, P.; Roncali, J. J. Mol. Struct. (Theochem) 2004, 709, 187. https://doi.org/10.1016/j.theochem.2003.10.082
  44. Abraham, J. P.; Sajan, D.; Shettigar, V.; Dharmaprakash, S. M.; Nemec, I.; Hubert Joe, I.; Jayakumar, V. S. J. Mol. Struct. 2009, 917, 27. https://doi.org/10.1016/j.molstruc.2008.06.031
  45. Destri, S.; Khotina, I. A.; Porzio, W. Macromolecules 1998, 3, 1079.
  46. Karakas, A.; Elmali, A.; Unver, H. J. Nonlinear Optic. Phys. Mat. 2007, 16, 91. https://doi.org/10.1142/S0218863507003573
  47. Koopmans, T. Physica 1933, 1, 104.
  48. Tanak, H. J. Mol. Struct. (Theochem) 2010, 950, 5. https://doi.org/10.1016/j.theochem.2010.03.015

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