Synthesis, spectral characterization, molecular structure, HOMO-LUMO, MEP and NLO analysis of some (E)-N-(4-Fluoro-3-Phenoxybenzylidene)- substituted benzenamines

  • Authors

    • G. Jesu Retna Raj ASSOCIATE PROFESSOR,PG & RESEARCH DEPT. CHEMISTRY, GOVT. ARTS COLLEGE, CHIDAMBARAM.
    • P. Jayanthi RESEARCH SCHOLAR
    • M. Sekar RESEARCH SCHOLAR
    2016-11-23
    https://doi.org/10.14419/ijac.v4i2.6742
  • DFT, HOMO – LUMO Energies, NLO, MEP, Substituted Benzenamines.

  • Abstract

    In this work, (E)-N-(4-Fluoro-3-Phenoxybenzylidene)-substituted benzenamines (1-6) have been synthesized and characterized by IR, 1H and 13C NMR spectral studies. Density functional theory (DFT) has been used to optimize geometrical parameters, atomic charges, vibrational wavenumbers and intensity of vibrational bands. The molecular properties HOMO-LUMO, MEP and atomic charges of carbon, nitrogen and oxygen were calculated using B3LYP/6-311G (d, p) basis set. The polarizability and first order hyperpolarizability of the title Compounds were calculated and interpreted.

  • References

    1. [1] Sinha, D., Tiwari, A.K., Singh, S., Shukla, G., Mishra, P., Chandra, H., and Mishra, A.K., 2008, Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde, Eur. J. Med. Chem,. 43, 160 - 165. https://doi.org/10.1016/j.ejmech.2007.03.022.

      [2] Crowe, A. J., Smith, P.J. and Atassi, G., 1980, Investigations into the antitumour activity of organotin compounds. I. Diorganotin dihalide and di-pseudohalide complexes Chem. Biol. Interact., 32, 171 - 178. https://doi.org/10.1016/0009-2797(80)90075-7.

      [3] Wang, M., Wang, L.F., Li, Y.Z., Li, Q.X., Xu , Z.D. and Qu, D.M., 2001, Antitumour activity of transition metal complexes with the thiosemicarbazone derived from 3-acetylumbelliferone, Transit. Met.Chem., 26, 307 - 310. https://doi.org/10.1023/A:1007159301849.

      [4] Przybylski, P., Pyta, K., Wicher, B., Gdaniec, M., and Brzezinsk, B., 2008, Structure of a new Schiff base of gossypol with 1-(3-aminopropyl)-2-pyrrolidinone studied by the X-ray, FT-IR, NMR, ESI-MS and PM5 methods, J. Mol. Struct., 889, 332 - 343. https://doi.org/10.1016/j.molstruc.2008.02.028.

      [5] Desai, S.B., Desai, P.B. and Desai, K.R., 2001, Synthesis of some schiff bases,thiazolidinones and azetidinones derived from 2,6-diaminobenzo[1,2-d:4,5-d'] bisthiazole and their anticancer activities, Heterocycl. Commun, 7, 83- 90. https://doi.org/10.1515/HC.2001.7.1.83.

      [6] Shivakumar, K., Shashidhar, P., Vithalreddy , Halli, M. B., 2008, Synthesis, Spectral Characterization and biological activity of benzofuran Schiff bases with Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) Complexes, J. Coord Chem , 61(14), 2274-2287. https://doi.org/10.1080/00958970801905239.

      [7] Przybylski, P., Huczynski, A., Pyta, K., Brzezinski, B., and Bartl, F., 2009, Biological Properties of Schiff Bases and Azo Derivatives of Phenols, Curr. Org. Chem., 13, 124 - 148. https://doi.org/10.2174/138527209787193774.

      [8] Pandeya, S.N., Sriram, D., Nath, G., and DeClercq, E., 1999, Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one, Pharm. Acta Helv., 74, 11- 17. https://doi.org/10.1016/S0031-6865(99)00010-2.

      [9] Karthikeyan, M.S., Parsad, D.J., Poojary, B., Bhat, K.S., Holla, B.S. and Kumari, N.S., 2006, Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety, Bioorg.Med. Chem., 14, 7482 - 7489. https://doi.org/10.1016/j.bmc.2006.07.015.

      [10] Holla, B.S., Akberali, P.M., and Shivananda, M.K., 2001, Studies on nitrophenylfuran derivatives Part XII. Synthesis, characterization, antibacterial and antiviral activities of some nitrophenylfurfurylidene-1, 2, 4-triazolo [3, 4-b]-1, 3, 4-thiadiazines, Il Farmaco., 56, 919 - 927. https://doi.org/10.1016/S0014-827X(01)01124-7.

      [11] Jarrahpour, A., Khalili, D., De Clercq, E., Salmi, C., and Brune,l J.M., 2007, Synthesis, Antibacterial, Antifungal and Antiviral Activity Evaluation of Some New bis-Schiff Bases of Isatin and Their Derivatives, Molecules., 12, 1720 - 1730. https://doi.org/10.3390/12081720.

      [12] da Silva, C.M., da Silva, D.L., Modolo, L.V., Alves, R.B., de Resende, M.A., Martins, C.V.B. and de Fatima, A., 2011, Schiff bases: A short review of their antimicrobial activities, J. Adv. Res., in press, https://doi.org/10.1016/j.jare.2010.05.004.

      [13] Singh, H., Yadav, L.D.S., and Mishra, S.B.S., 1981, Studies on some antifungal transition metal chelates of N-(5-phenyl-1, 3, 4-thiadiazol-2-yl) dithiocarbamic acid, J. Inorg. Nucl.Chem., 43, 1701 - 1704. https://doi.org/10.1016/0022-1902(81)80367-3.

      [14] Saravanan, G., Pannerselvam, P. and Prakash, C.R., 2010, Synthesis and anti-microbial screening of novel schiff bases of 3-amino-2-methyl quinazolin 4-(3H)-one, J. Adv. Pharm. Techn., Res. 1, 320 - 325.

      [15] Panneerselvam, P., Nair, R.R., Vijayalakshmi, G., Subramanian, E.H. and Sridhar, S.K., 2005, Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents, Eur. J.Med. Chem., 40, 225. https://doi.org/10.1016/j.ejmech.2004.09.003.

      [16] Singh, N.K., and Singh, S.B., 2001, Synthesis characterization and biological properties of manganese (II), cobalt(II), nickel (II), copper(II), zinc(II), chromium(III) and iron(III) compiexes with a new thiosemicarbazide derivative, Indian J. Chem. 40A, 1070 - 1075.

      [17] Walsh, O.M., Meegan, M.J., Prendergast, R.M., and Nakib, T.A., 1996, Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity, Eur. J. Med. Chem., 31, 989 - 1000. https://doi.org/10.1016/S0223-5234(97)86178-8.

      [18] Odabasoglu, M., Arslan, F., Ölmez, H., and Büyükgüngör, O., 2007, Synthesis, crystal structures and spectral characterization of trans-bisaquabis(o-vanillinato)copper(II), cis-aquabis(o-vanillinato)copper(II) and aqua[bis(o-vanillinato)-1,2-ethylenediimin]copper(II) , Dyes and Pigments., 75, 507 - 515. https://doi.org/10.1016/j.dyepig.2006.06.033.

      [19] Vicini, P., Geronikaki, A., Incerti, M., Busonera, B., Poni, G., Cabras, C.A., and Colla, P.L., 2003, Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases, Bioorg.Med. Chem., 11, 4785 - 4789. https://doi.org/10.1016/S0968-0896(03)00493-0.

      [20] Pandeya, S.N., Sriram, D., Nath, G. and DeClercq, E., 1999, Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl) thiazol-2-yl] thiosemicarbazide, Eur. J. Pharm. Sci., 9, 25 - 31. https://doi.org/10.1016/S0928-0987(99)00038-X.

      [21] Szady-Chelmieniecka, A., Grech, E., Rozwadowski, Z ., Dziembowska,T., ,.Schilf, W., and Kamienski, B., 2001, Multinuclear NMR study of the intramolecular hydrogen bond in Schiff–Mannich bases, J. Mol. Struct., 565, 125- 128. https://doi.org/10.1016/S0022-2860(00)00788-2.

      [22] Dhanaraj, C.J. and Nair, M.S., 2009, Synthesis, characterization, and antimicrobial studies of some Schiff-base metal(II) complexes, J. Co ord. Chem., 62, 4018 - 4028. https://doi.org/10.1080/00958970903191142.

      [23] Schilf, W., Kamienski, B., and Dziembowska, T., 2002, Intramolecular hydrogen bond investigations in Schiff bases derivatives of 2-hydroxy-1-naphthaldehyde and 2-hydroxy-1-acetonaphthone in CDCl3 solution and in the solid state by NMR methods. J. Mol. Struct., 602, 41- 47. https://doi.org/10.1016/S0022-2860(01)00742-6.

      [24] Yuan, H., Graefenstein, J., Kraka, E., and Cremer, D., 2000, What correlation effects are covered by density functional theory?, Molecular Physics., 98:20 1639 - 1658.

      [25] Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B.,. Petersson,G.A., Nakatsuji, H., Caricato, M.X., LiHratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G.J., Sonnenberg, L., Hada ,M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima,T., Honda ,Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, Jr., J.E., Ogliaro, F., Bearpark, M.J., Heyd, J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C.,. Iyengar, S.S., Tomasi, J. Cossi, M., Rega, N. Millam, ., J. M., Klene, M.,. Knox, J.E., Cross, J.B., Bakken, V.C., Adamo, Jaramillo, J., Gomperts, R. Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J,. Dapprich, S., Daniels, A.D., Farkas, O., Foresman ,J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J., 2004., Gaussian 03, Revision C.02, Gaussian Inc., Wallinford, CT,

      [26] Prasad, O., Sinha,L., Kumar, N., Theoretical Raman and IR spectra of tegafur and comparison of molecular electrostatic potential surfaces, polarizability and hyerpolarizability of tegafur with 5-fluoro-uracil by density functional theory, J. Atom Mol. Sci., 2010, 1, 201. https://doi.org/10.4208/jams.032510.042010a.

      [27] Kavitha, E. Sundaraganesan, N., Sebastin, S., 2010, Molecular structure, vibrational spectroscopic and HOMO, LUMO studies of 4-nitroaniline by density functional method, Ind. J. Pure Appl. Phys., 48, 20 – 30.

      [28] Koopmans, T., 1934, Ãœber die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms Physica, 1, 104 - 113.

      [29] Arockia doss, M.; Savithiri, S.; Rajarajan,G.; Thanikachalam,V.; Saleem, H. Synthesis, spectroscopic (FT-IR, FT-Raman, UV and NMR) and computational studies on 3t-pentyl-2r,6c-diphenylpiperidin-4-one semicarbazone. Spectrochim Acta Part A. 2015, 148, 189-202. https://doi.org/10.1016/j.saa.2015.03.117.

      [30] Arockia doss, M., Savithiri, S., Rajarajan, G., Thanikachalam, V., Anbuselvan, C., 2015, Synthesis, electronic structure investigation of 3-pentyl-2,6-di(furan-2-yl)piperidin-4-one by FT-IR, FT-Raman and UV–Visible spectral studies and ab initio/DFT calculations, Spectrochimica Acta Part A, 151, 773.

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  • How to Cite

    Raj, G. J. R., Jayanthi, P., & Sekar, M. (2016). Synthesis, spectral characterization, molecular structure, HOMO-LUMO, MEP and NLO analysis of some (E)-N-(4-Fluoro-3-Phenoxybenzylidene)- substituted benzenamines. International Journal of Advanced Chemistry, 4(2), 27-35. https://doi.org/10.14419/ijac.v4i2.6742

    Received date: 2016-09-13

    Accepted date: 2016-10-11

    Published date: 2016-11-23