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2016 | 130 | 6 | 1273-1287
Article title

Theoretical Studies of Molecular Structures, Infrared Spectra, NBO and NLO Properties of Some Novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone Dyes

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Abstracts
EN
The optimized geometrical structures, infrared spectra, molecular electrostatic potential, natural bond orbital and nonlinear optical properties of 5-phenylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridoine (1) and 5-(4-bromophenylazo)-6-hydroxy-4-phenyl-3-cyano-2-pyridoine (2) dyes with a detailed study on the azo-hydrazone tautomerism in the ground state have been investigated by density functional theory using B3LYP functional with 6-31G(d,p) basis set. Vibrational modes are assigned with the help of vibrational energy distribution analysis program. Highest occupied molecular orbital and lowest unoccupied molecular orbital energies of the (1) and (2) compounds with azo and hydrazone forms were calculated with the same method and basis set. Molecular parameters like global hardness (η), global softness (σ) and electronegativity (χ) were calculated with the results obtained from the highest occupied and lowest unoccupied molecular orbital energies. Nonlinear optical parameters (mean polarizability (⟨α⟩), the anisotropy of the polarizability (⟨Δα⟩) and the mean first-order hyperpolarizability (⟨β⟩)) of the title compounds were investigated theoretically. The atomic charges, electronic exchange interaction, and charge delocalization of the molecules have been studied by natural bond orbital analysis.
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Publisher

Year
Volume
130
Issue
6
Pages
1273-1287
Physical description
Dates
published
2016-12
received
2016-02-18
(unknown)
2016-11-05
Contributors
author
  • Department of Elementary Science Education, Kocaeli University, 41380, Umuttepe, Kocaeli, Turkey
author
  • Department of Physics, Science and Art Faculty, Kocaeli University, 41380, Umuttepe, Kocaeli, Turkey
References
  • [1] H. Çetişli, M. Karakuş, E. Erdem, H. Deligöz, J. Incl. Phenom. Macro. 42, 187 (2002), doi: 10.1023/A:1016072604774
  • [2] C.S. Wang, H.S. Fei, Y. Qiu, Y.Q. Yang, Z.Q. Wei, Y.Q. Tian, Y.M. Chen, Y.Y. Zhao, Appl. Phys. Lett. 74, 19 (1999), doi: 10.1063/1.123138
  • [3] H. Zollinger, Colour Chemistry, VCH, Weinheim 1987
  • [4] C.C. Chen, I.J. Wang, Dyes Pigm. 15, 69 (1991), doi: 10.1016/0143-7208(91)87008-B
  • [5] W. Huang, H. Qian, Dyes Pigm. 77, 446 (2008), doi: 10.1016/j.dyepig.2007.07.012
  • [6] W. Huang, Dyes Pigm. 79, 69 (2008), doi: 10.1016/j.dyepig.2008.01.007
  • [7] C. Lubai, C. Xing, G. Kunyu, H. Jiezhen, J. Griffiths, Dyes Pigm. 7, 373 (1986), doi: 10.1016/j.dyepig.2008.01.007
  • [8] A. Cee, B. Horáková, A. Lyčka, Dyes Pigm. 9, 357 (1988), doi: 10.1016/j.dyepig.2008.01.007
  • [9] G.S. Ušćumlić, D.Z. Mijin, N.V. Valentić, V.V. Vajs, B.M. Sušić, Chem. Phys. Lett. 397, 148 (2004), doi: 10.1016/j.cplett.2004.07.057
  • [10] Industrial Dyes: Chemistry, Properties, Applications, Ed. K. Hunger, Wiley-VCH, 2003, doi: 10.1002/3527602011
  • [11] A. Alimmari, D. Mijin, R. Vukićević, B. Božić, N. Valentić, V. Vitnik, Ž. Vitnik, G. Ušćumlić, Chem. Cent. J. 6, 71 (2012), doi: 10.1186/1752-153X-6-71
  • [12] M.J. Frisch, G.W. Trucks, H.B. Schlegal, G.E. Scuseria, M.A. Robb, J.R. Cheesman, V.G. Zakrzewski, J.A. Jr. Mortgomerg, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, J. Mennucci, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malich, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stetanov, G. Liu, A. Liashenko, P. Piskorz, J. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al. Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chenp, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 09, Revision A.1, Gaussian Inc., Wallingford (CT) 2009 http://gaussian.com/g_prod/g09.htm
  • [13] M.J. Frisch, G.W. Trucks, H.B. Schlegel, GaussView, Ver. 5.0.9, Semichem. Inc., Shawnee Mission (KS) 2009
  • [14] A.D. Becke, J. Chem. Phys. 98, 5648 (1993), doi: 10.1063/1.464913
  • [15] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988), doi: 10.1103/PhysRevB.37.785
  • [16] M.H. Jamroz, VEDA 4 Program, Warsaw 2004
  • [17] A.P. Scott, L. Radom, J. Phys. Chem. 100, 16502 (1996), doi: 10.1021/jp960976r
  • [18] J.B. Foresman, A. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian Inc., Pittsburgh 1996
  • [19] E.D. Glendening, C.R. Landis, F. Weinhold, Comput. Mol. Sci. 2, 1 (2011), doi: 10.1002/wcms.51
  • [20] T.C. Koopmans, Physica (Amsterdam) 1, 104 (1933)
  • [21] P. Senet, Chem. Phys. Lett. 275, 527 (1997), doi: 10.1016/S0009-2614(97)00799-9
  • [22] L. Pauling, The Nature of the Chemical Bond, Cornell University Press, Ithaca 1960
  • [23] A. Hinchliffe, B. Nikolaidi, H.J.S. Machado, Int. J. Mol. Sci. 5, 224 (2004), doi: 10.3390/i5050224
  • [24] A.D. Buckingham, Adv. Chem. Phys. 12, 107 (1967), doi: 10.1002/9780470143582.ch2
  • [25] A.D. Mclean, M. Yoshimine, J. Chem. Phys. 47, 1927 (1967), doi: 10.1063/1.1712220
  • [26] C. Lin, K. Wu, Chem. Phys. Lett. 321, 83 (2000), doi: 10.1016/S0009-2614(00)00323-7
  • [27] J.P. Abraham, D. Sajan, I.J. Hubert, V.S. Jayakumar, Spectrochim. Acta A 71, 355 (2008), doi: 10.1016/j.saa.2008.01.010
  • [28] P. Karamanis, C. Pouchan, G. Maroulis, Phys. Rev. A 77, 013201 (2008), doi: 10.1103/PhysRevA.77.013201
  • [29] A. Ben Ahmed, H. Feki, Y. Abid, H. Boughzala, A. Mlayah, J. Mol. Struct. 888, 180 (2008), doi: 10.1016/j.molstruc.2007.11.056
  • [30] A. Streitwieser Jr., Molecular Orbital Theory for Organic Chemists, Wiley, New York 1961
  • [31] K. Fukui, Science 218, 747 (1982), doi: 10.1126/science.218.4574.747
  • [32] J. Dostanić, D. Mijin, G. Ušćumlić, D.M. Jovanović, M. Zlatar, D. Lončarević, Spectrochim. Acta A 123, 37 (2014), doi: 10.1016/j.saa.2013.12.064
  • [33] J. Mirković, J. Rogan, D. Poleti, V. Vitnik, Ž. Vitnik, G. Ušćumlić, D. Mijin, Dyes Pigments 104, 160 (2014), doi: 10.1016/j.dyepig.2014.01.007
  • [34] A. Esme, S.G. Sagdinc, J. Mol. Struct. 1048, 185 (2013), doi: 10.1016/j.molstruc.2013.05.022
  • [35] A. Temel, S. Ozbey, N. Ertan, Dyes Pigm. 32, 237 (1996), doi: 10.1016/S0143-7208(96)00028-9
  • [36] L.C. Abbott, S.N. Batchelor, J. Oakes, B.C. Gilbert, A.C. Whitwood, J.R.L. Smith, J.N. Moore, J. Phys. Chem. A 109, 2894 (2005), doi: 10.1021/jp045216s
  • [37] M.R. Almeida, R. Stephani, H.F. Dos Santos, L.F.C. De Oliveira, J. Phys. Chem. A 114, 526 (2010), doi: 10.1021/jp907473d
  • [38] V. Bertolasi, L. Nanni, P. Gilli, V. Ferreti, G. Gilli, New J. Chem. 18, 251 (1994)
  • [39] F.H. Allen, O. Kennard, D. Watson, L. Brammer, A.G. Orpen, R. Taylor, J. Chem. Soc. 2, S1 (1987)
  • [40] D.B. Pendergrass, I.C. Paul, D.Y. Curtin, J. Am. Chem. Soc. 94, 8730 (1972), doi: 10.1021/ja00780a016
  • [41] P.K. Chattaraj, S. Nath, B. Maiti, Computational Medicinal Chemistry for Drug Discovery, Marcel Dekker, New York 2003
  • [42] R.G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, Oxford 1989
  • [43] P. Politzer, J. Murray, Theor. Chem. Acc. 108, 134 (2002), doi: 10.1007/s00214-002-0363-9
  • [44] P. Politzer, J.S. Murray, Theoretical Biochemistry and Molecular Biophysics: A Comprehensive Survey, Adenine Press, New York 1991
  • [45] O. Prasad, L. Sinha, N. Kumar, J. At. Mol. Sci. 1, 201 (2010), doi: 10.4208/jams.032510.042010a
  • [46] Y.G. Sidir, I. Sidir, J. Sci. Technol. 1, 7 (2011)
  • [47] F. Weinhold, C.R. Landis, Chem. Educ. Res. Pract. Eur. 2, 91 (2001), doi: 10.1039/B1RP90011K
  • [48] M. Kaur, Y.S. Mary, H.T. Varghese, C.Y. Panicker, H.S. Yathirajan, M.S. Siddegowda, C. Van Alsenoy, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 98, 91 (2012), doi: 10.1016/j.saa.2012.08.061
  • [49] Y. Matsuda, T. Ebata, N. Mikami, J. Chem. Phys. 110, 8397 (1999), doi: 10.1063/1.478748
  • [50] G. Varsanyi, Assignment for Vibrational Spectra of Seven Hundred Benzene Derivatives, Academic Kiaclo, Budapest 1973
  • [51] M. Jag, Organic Spectroscopy-Principles and Applications, Narosa Publ. House, New Delhi 2001
  • [52] M. Snehalatha, C. Ravikumar, I.J. Hubert, Solid State Sci. 11, 1275 (2009), doi: 10.1016/j.solidstatesciences.2009.03.022
  • [53] J.B. Labbert, H.F. Shurvel, L. Verbit, R.G. Cooks, G.H. Stout, Organic Structural Analysis, Macmillan Publ. Co. Inc., New York 1976
  • [54] H.P. Gümüş, O. Tamer, D. Avci, Y. Atalay, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 132, 183 (2014), doi: 10.1016/j.saa.2014.04.128
  • [55] A.J. LaPlante, H.D. Stidham, Spectrochim. Acta A 74, 808 (2009), doi: 10.1016/j.saa.2009.08.015
  • [56] W. Zierkiewicz, D. Michalska, T.H. Zeegers-Huyskens, J. Phys. Chem. A 104, 11685 (2000), doi: 10.1021/jp0020788
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.bwnjournal-article-appv130n604kz
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