PL EN


Preferences help
enabled [disable] Abstract
Number of results
2015 | 127 | 3 | 701-710
Article title

Theoretical Investigation of N-Methyl-N'-(4-nitrobenzylidene) pyrazine-2-carbohydrazide: Conformational Study, NBO Analysis, Molecular Structure and NMR Spectra

Content
Title variants
Languages of publication
EN
Abstracts
EN
The crystal structure determination of the methylated pyrazine-2-carbohydrazide derivative, namely N-methyl-N'-(4-nitrobenzylidene)pyrazine-2-carbohydrazide were optimized to obtain its molecular geometric structure and electronic structures at the Hartree-Fock and density functional theory levels (B3LYP) with 6-311G(d,p) and 6-311++G(d,p) basis sets, using Gaussian 09W programme. The ^{1}H and ^{13}C nuclear magnetic resonance chemical shifts of the title molecule were calculated by using the gauge independent atomic orbital, continuous set of gauge transformations and individual gauges for atoms in molecules methods and were also compared with experimental values. The electronic properties high occupied and low unoccupied molecular orbitals energies were calculated and analyzed. Potential energy surface scan, natural population analysis and Mulliken atomic charges were investigated using theoretical calculations. A detailed molecular picture and intermolecular interactions arising from hyperconjugative interactions and charge delocalization of the molecule were analyzed using natural bond orbital analysis.
Keywords
Contributors
author
  • Beykent University, Department of Health Programmes, Opticianry Programme, İstanbul, Turkey
author
  • Sakarya University, Faculty of Arts and Sciences, Department of Physics, 54187, Sakarya, Turkey
author
  • Beykent University,Faculty of Enginering, Department of Chemical Enginering, İstanbul, Turkey
author
  • Sakarya University, Faculty of Arts and Sciences, Department of Physics, 54187, Sakarya, Turkey
author
  • Sakarya University, Faculty of Arts and Sciences, Department of Physics, 54187, Sakarya, Turkey
References
  • [1] A.K. Singh, P. Kumar, M. Yadav, D.S. Pandey, J. Organomet. Chem. 695, 567 (2010), doi: 10.1016/j.jorganchem.2009.11.011
  • [2] X.H. Zhao, S.S. Liu, Y.Z. Li, M.D. Chen, Spectrochim. Acta A 75, 794 (2010), doi: 10.1016/j.saa.2009.11.057
  • [3] T. Asaki, T. Hamamoto, Y. Sugiyama, K. Kuwano, K. Kuwabara, Bioorgan. Med. Chem. 15, 6692 (2007), doi: 10.1016/j.bmc.2007.08.010
  • [4] J.W. Corbett, M.R. Rauckhorst, F. Qian, R.L. Hoffman, C.S. Knauer, L.W. Fitzgerald, Bioorgan. Med. Chem. 17, 6250 (2007), doi: 10.1016/j.bmcl.2007.09.008
  • [5] H. Endredi, F. Billes, F.S. Holly, J. Mol. Struct. 633, 73 (2003), doi: 10.1016/S0166-1280(03)00329-4
  • [6] S.R. Pattan, P.A. Rabara, J.S. Pattan, A.A. Bukitagar, V.S. Wakale, D.S. Musmade, Indian J. Chem. 48, 1453 (2009)
  • [7] D. Sriram, P. Yogeeswari, S.P. Reddy, Bioorgan. Med. Chem. Lett. 16, 2113 (2006), doi: 10.1016/j.bmcl.2006.01.064
  • [8] L.R. Gomes, J.N. Low, A.S.M.C. Rodrigues, J.L. Wardell, C.H. Lima, M.V.N. de Souza, Acta Crystallogr. C 69, 549 (2013), doi: 10.1107/S0108270113010056
  • [9] S.M. Sondhi, M. Dinodia, A. Kumar, Eur J. Med. Chem. 44, 1010 (2009), doi: 10.1016/j.ejmech.2008.06.029
  • [10] A. Tanitame, Y. Oyamada, K. Ofuji, H. Terauchi, M. Kawasaki, M. Wachi, J.-I. Yamagishi, Bioorgan. Med. Chem. Lett. 15, 4299 (2005), doi: 10.1016/j.bmcl.2005.06.103
  • [11] I. Koca, A. Özgür, K.A. Coşkun, Y. Tutar, Bioorgan. Med. Chem. 21, 3859 (2013), doi: 10.1016/j.bmc.2013.04.021
  • [12] S. Tyagarajan, P.K. Chakravarty, B. Zhou, B. Taylor, R. Eid, M.H. Fisher, W.H. Parsons, M.J. Wyvratt, K.A. Lyons, T. Klatt, X. Li, S. Kumar, B. Williams, J. Felix, B.T. Priest, R.M. Brochu, V. Warren, M. Smith, M. Garcia, G.J. Kaczorowski, W.J. Martin, C. Abbadie, E. McGowan, N. Jochnowitz, A. Weber, J.L. Duffy, Bioorgan. Med. Chem. Lett. 20, 7479 (2010), doi: 10.1016/j.bmcl.2010.10.017
  • [13] S.-R. Shih, T.-Y. Chu, G. Reddy, S.-N. Tseng, H.-L. Chen, W.-F. Tang, M.-S. Wu, J.-Y. Yeh, Y.-S. Chao, J.T.A. Hsu, H.-P. Hsieh, J.-T. Horng, J. Biomed. Sci. 17, 13 (2010), doi: 10.1186/1423-0127-17-13
  • [14] H.Y. Lo, C.C. Man, R.W. Fleck, N.A. Farrow, R.H. Ingraham, A. Kukulka, J.R. Proudfoot, R. Betageri, T. Kirrane, U. Patel, R. Sharma, M.A. Hoermann, A. Kabcenell, S. de Lombaert, Bioorgan. Med. Chem. Lett. 26, 6379 (2010), doi: 10.1016/j.bmcl.2010.09.095
  • [15] R. Kasimoğullari, M. Bülbül, B.S. Arslan, B. Gökçe, Eur. J. Med. Chem. 45, 4769 (2010), doi: 10.1016/j.ejmech.2010.07.041
  • [16] A. Padmaja, C. Rajasekhar, A. Muralikrishna, V. Padmavathi, Eur. J. Med. Chem. 46, 5034 (2011), doi: 10.1016/j.ejmech.2011.08.010
  • [17] N. Gökhan-Kelekçi, S. Koyunoglu, S. Yabanoglu, K. Yelekçi, Ö. Özgen, G. Uçar, K. Erol, E. Kendi, A. Yeşilada, Bioorgan. Med. Chem. 17, 675 (2009), doi: 10.1016/j.bmc.2008.11.068
  • [18] D.M. Shen, E.J. Brady, M.R. Candelore, Q. Dallas-Yang, V.D.-H. Ding, W.P. Feeney, G. Jiang, M.E. McCann, S. Mock, S.A. Qureshi, R. Saperstein, X. Shen, X. Tong, L.M. Tota, M.J. Wright, X. Yang, S. Zheng, K.T. Chapman, B.B. Zhang, J.R. Tata, E.R. Parmee, Bioorgan. Med. Chem. Lett. 21, 76 (2011), doi: 10.1016/j.bmcl.2010.11.074
  • [19] K. Gobis, H. Foks, Z. Zwolska, E. Augustynowicz-Kopeć, Heterocycles 81, 917 (2010), doi: 10.3987/COM-09-11888
  • [20] S.M.S.V. Wardell, M.V.N. de Souza, J.L. Wardell, J.N. Low, C. Glidewell, Acta Crystallogr. E 62, 3765 (2006), doi: 10.1107/S1600536806029394
  • [21] M. Yoshida, T. Shimada, T. Ishida, T. Kogane, Polyhedron 66, 75 (2013), doi: 10.1016/j.poly.2013.02.033
  • [22] B. Milczarska, K. Gobis, H. Foks, L. Golunski, P. Sowinski, J. Heterocyclic Chem. 49, 845 (2012), doi: 10.1002/jhet.877
  • [23] A.D. Becke, J. Chem. Phys. 98, 5648 (1993), doi: 10.1063/1.464913
  • [24] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988), doi: 10.1103/PhysRevB.37.785
  • [25] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A.1, Gaussian Inc., Wallingford CT, 2009
  • [26] R. Dennington, T. Keith, J. Millam, Semichem Inc., Shawnee Mission KS, GaussView, Version 5, 2009
  • [27] E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO version 3.1
  • [28] H. Pir, N. Gunay, Ö. Tamer, D. Avci, E. Tarcan, Y. Atalay, Mater. Sci.-Poland 31, 357 (2013), doi: 10.2478/s13536-013-0112-x
  • [29] Ö. Tamer, D. Avci, Y. Atalay, Spectrochim. Acta A 117, 78 (2014), doi: 10.1016/j.saa.2013.07.112
  • [30] A. Kunduracioğlu, Ö. Tamer, D. Avci, İ. Kani, Y. Atalay, B. Çetinkaya, Spectrochim. Acta A 121, 35 (2014), doi: 10.1016/j.saa.2013.10.075
  • [31] R. Ditchfield, J.`Chem. Phys. 56, 5688 (1972), doi: 10.1063/1.1677088
  • [32] T.A. Keith, R.F.W. Bader, Chem. Phys. Lett. 210, 223 (1993), doi: 10.1016/0009-2614(93)89127-4
  • [33] T.A. Keith, R.F.W. Bader, Chem. Phys. Lett. 194, 1 (1992), doi: 10.1016/0009-2614(92)85733-Q
  • [34] K. Fukui, Science 218, 747 (1982), doi: 10.1126/science.218.4574.747
  • [35] R.G. Parr, R.G. Pearson, J. Am. Chem. Soc. 105, 7512 (1983), doi: 10.1021/ja00364a005
  • [36] Ö. Tamer, N. Dege, G. Demirtaş, D. Avci, Y. Atalay, M. Macit, A. Alaman Agar, Spectrochim. Acta A 117, 13 (2014), doi: 10.1021/ja00364a005
  • [37] N. Dege, N. Şenyüz, H. Bati, N. Günay, D. Avci, Ö. Tamer, Y. Atalay, Spectrochim. Acta A 120, 323 (2014), doi: 10.1016/j.saa.2013.10.030
  • [38] R.G. Pearson, Proc. Natl. Acad. Sci. 83, 8440 (1986), doi: 10.1073/pnas.83.22.8440
  • [39] A.E. Reed, L.A. Curtiss, F. Weinhold, Chem. Rev. 88, 899 (1988), doi: 10.1021/cr00088a005
  • [40] D.G. Truhlar, J. Chem. Phys. 82, 2418 (1985), doi: 10.1063/1.448335
  • [41] S. Sebastian, N. Sundaraganesan, Spectrochim. Acta A 75, 941 (2010), doi: 10.1016/j.saa.2009.11.030
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.bwnjournal-article-appv127n308kz
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.