Synthesis and vibrational spectral (FT-IR, FT-Raman) studies, NLO properties & NBO analysis of (E)-N'(thiophen-2yl methylene)isonicotinohydrazide using quantum chemical method
DOI:
https://doi.org/10.14419/ijac.v6i1.9046Keywords:
FT-IR, FT-Raman, NBO, HOMO-LUMO, Molecular Docking.Abstract
FT-IR (4000-400 cm-1) and FT-Raman (3500-50 cm-1) spectra of (E)-N'(thiophen-2yl methylene)isonicotinohydrazide (TMINH) molecule was recorded in solid phase. The optimized geometry was calculated by B3LYP method with 6-311++G(d,p) basis set. The harmonic vibrational frequencies, infrared (IR) intensities and Raman scattering activities of the title compound were performed at same level of theory. The complete vibrational assignments were performed on the basis of the Total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanical (SQM) method. The calculated first hyperpolarizability may be attractive for further studies on non-linear optical (NLO) properties of material. Stability of the molecule arising from
hyperconjugative interaction and charge delocalization was analyzed using natural bond orbital (NBO) analysis. Highest occupied molecular orbital-Lowest unoccupied molecular orbital (HOMO-LUMO) energy gap explains the eventual charge transfer
interactions taking place within the title molecule. A study on the electronic properties, such as excitation energies and wavelengths, were performed by time-dependent (TD-DFT) approach. Molecular electrostatic potential (MEP) provides the information on the electrophilic, nucleophilic and free radical prone reactive sites of the molecule. The thermodynamic properties such as heat capacity, entropy and enthalpy of the title compound were calculated at different temperatures in gas phase. 1H and 13C-NMR chemical shifts of the molecule were calculated using Gauge-independent atomic orbital (GIAO) method.To establish information about the
interactions between human cytochrome protein and this novel compound theoretically, docking studies were carried out using Schrödinger software.
References
[1] Davidson, E.R., 2000, Computational Transition Metal Chemistry, Chemical Reviews, 100(2), 351–352. https://doi.org/10.1021/cr980385s.
[2] Molvi, K.I., Vasu, K.K., Yerande, S.G., Sudarsanam, V., &Haque, N., 2007, Syntheses of new tetrasubstitutedthiophenes as novel
anti-inflammatory agents, Eur. J. Med. Chem, 42(8), 1049–1058. https://doi.org/10.1016/j.ejmech.2007.01.007.[3] SatheeshaRai, N., Kalluraya, B., Lingappa, B., Shenoy, S., &Puranic, V.G., 2008, Convenient access to 1,3,4-trisubstituted
pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar
cycloaddition of sydnones with acetylenic ketones and their
antimicrobial evaluation, Eur. J. Med. Chem. 43(8), 1715–1720, https://doi.org/10.1016/j.ejmech.2007.08.002.[4] Ashalatha, B.V., Narayana, B., Vijaya Raj, K.K., & Suchetha
Kumari, N., 2007, Synthesis of some new bioactive 3-amino-2-mercapto-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one derivatives, Eur. J. Med. Chem. 42(5), 719–728. https://doi.org/10.1016/j.ejmech.2006.11.007.[5] PolÃvka, Z., Holubek, J., Svátek, E., MetyÅ¡, J., &Protiva, M., 1984, Potential hypnotics and anxiolytics: Synthesis of 2-bromo-4-(2-chlorophenyl)-9-[4-(2-methoxyethyl)piperazino]-6H-thieno [3,2,4-triazolo[4,3-a]-1,4-diazepine and of some related compounds,
Collect. Czech. Chem. Commun. 49(3), 621–636. https://doi.org/10.1135/cccc19840621.[6] Noguchi, H., Kitazumi, K., Mori, M., &Shiba, T., 2004,
Electroencephalographic Properties of Zaleplon, a Non-Benzodiazepine Sedative/Hypnotic, in Rats, J. Pharm. Sci. 94(3), 246–251. doi:10.1254/jphs.94.246.https://doi.org/10.1254/jphs.94.246.[7] Guentert, M., Bertram, H.-J., Emberger, R., Hopp, R., Sommer, H., &Werkhoff, P., 2010, ChemInform Abstract: Thermal Degradation of Thiamin (Vitamin B1). A Comprehensive Survey of the Latest Studies. ChemInform, 25(49), no–no. https://doi.org/10.1002/chin.199449312.
[8] Press, J.B., 1991, the chemistry of heterocyclic compounds,
thiophene and it’s. Derivatives, in: Gronowitz, S., (Ed.), 44(4), 397–502, John Wiley and Sons, New York.[9] Bloor, D., 1995, Good conduct: Now that researchers have
overcome problems with synthesizing and manipulating conductive polymers, these materials are beginning to fulfil their early potential. Chemistry in Britain, 31(5), 385-385.[10] Nalwa, H.S., 1993, Organic Materials for Third-Order Nonlinear Optics, Advanced Materials, 5(5), 341–358. https://doi.org/10.1002/adma.19930050504.
[11] Wu, I.Y., Lin, J.T., Li, C.S., Wang, W.C., Huang, T.H., Wen, Y.S., Tsai, C., 1999, Preparation of push-pull type chromophores via
nitrothiophene induced Michael type reaction of alkynes,
Tetrahedron, 55(49), 13973–13982. https://doi.org/10.1016/S0040-4020(99)00871-6.[12] Mansour, A., Eid, M., & Khalil, N., 2003, Synthesis and Reactions of Some New Heterocyclic Carbohydrazides and Related
Compounds as Potential Anticancer Agents. Molecules, 8(12), 744–755. https://doi.org/10.3390/81000744.[13] Metwally, K.A., Abdel-Aziz, L.M., Lashine, E.S. M., Husseiny, M.I., &Badawy, R.H., 2006, Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents. Bio. Org. & Med. Chem., 14(24), 8675–8682. https://doi.org/10.1016/j.bmc.2006.08.022.
[14] Ghiglieri-Bertez, C., Coquelet, C., Alazet, A., & Bonne, C., 1987, Inhibiteursmixtes des voies de la cyclooxygénaseet des lipoxygénases: synthèse et activité de dérivéshydrazoniques, J. Med. Chem. 22(2), 147–152. https://doi.org/10.1016/0223-5234(87)90010-9.
[15] Gaussian 03 Program, 2004, Gaussian Inc, Wallingford CT.
[16] Frisch, A., Nielson, A.B., Holder, A.J., 2000, GAUSSVIEW User Manual Gaussian Inc. Pittsburgh, PA.
[17] Jamroz, M.H., 2004, Vibrational Energy Distribution Analysis, VEDA 4 Computer Program, Poland.
[18] Glendening, E.D., Reed, A.E., Carpenter, J.E., Weinhold, F., 1998, NBO Version 3.1, TCI, University of Wisconsin, Madison.
[19] 3LD6 reference from PDB.
[20] Protein Preparation Wizard; Epik Version 2.3, Impact version 5.7, Schrödinger, LLC, New York, 2014–4 release.
[21] Jorgensen, W.L., Maxwell, D.S., &Tirado-Rives, J., 1996,
Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids, J. Am. Chem. Soc. 118(45), 11225–11236. https://doi.org/10.1021/ja9621760.[22] Glide Version 5.8, Schrödinger, LLC, New York, 2014–4 release.
[23] Maestro, Schrödinger, LLC, New York, 2014–4 release.
[24] Ligprep, Version 2.5, Schrödinger, LLC, New York, 2014–4
release.[25] Balachandran, V., Janaki, A., &Nataraj, A., 2014, Theoretical
investigations on molecular structure, vibrational spectra, HOMO, LUMO, NBO analysis and hyperpolarizability calculations of
thiophene-2-carbohydrazide, 118, 321–330. https://doi.org/10.1016/j.saa.2013.08.091.[26] Fleming, G. D., Koch, R., & Campos Vallete, M. M. (2006).
Theoretical study of the syn and anti thiophene-2-aldehyde
conformers using density functional theory and normal coordinate analysis, SpectrochimActa A, 65(3-4), 935–945. https://doi.org/10.1016/j.saa.2006.01.038.[27] Song, M.Z., & Fan, C.G., 2009, (E)-N′-(2-Furylmethylene)benzohydrazide, ActaCrystallographica Sec. E Structure Reports, 65(11), o2800, https://doi.org/10.1107/S1600536809042251.
[28] Rauhut, G., &Pulay, P., 1995, Transferable Scaling Factors for Density Functional Derived Vibrational Force Fields. J. Phys. Chem., 99(10), 3093–3100. https://doi.org/10.1021/j100010a019.
[29] Nagabalasubramanian, P.B., Karabacak, M., &Periandy, S., 2012, Vibrational frequencies, structural confirmation stability and
HOMO–LUMO analysis of nicotinic acid ethyl ester with
experimental (FT-IR and FT-Raman) techniques and quantum
mechanical calculations. J. Mol. Struct., 1017, 1–13. https://doi.org/10.1016/j.molstruc.2012.02.042.[30] Krishnakumar, V., Balachandran, V., &Chithambarathanu, T., 2005, Density functional theory study of the FT-IR spectra of phthalimide and N-bromophthalimide, Spectrochimica, Acta Part A, 62(4-5), 918–925. https://doi.org/10.1016/j.saa.2005.02.051.
[31] Sundaraganesan, N., Saleem, H., Mohan, S., Ramalingam, M., &Sethuraman, V., 2005, FTIR, FT-Raman spectra and ab initio DFT vibrational analysis of 2-bromo-4-methyl-phenylamine,
SpectrochimicaActa Part A, 62(1-3), 740–751. https://doi.org/10.1016/j.saa.2005.02.043.[32] Singh, S.J., &Pandey, S.M., 1974, Molecular Structure and
vibrational analysis of 1-bromo-2-chlorobenzene using ab initio HF and density functional theory (B3LYP) calculations. Indian J Pure ApplPhys, 12, 300-304.[33] Varsanyi, G., 1973, Assignments for vibrational spectra of seven hundred benzene derivatives, vols.1 and 2, Academic kiado,
Budapest.[34] Jag, M., 2001, Organic Spectroscopy-Principles and Applications, 2nd ed, Narosa publishing House, New Delhi.
[35] Bharanidharan, S., Saleem, H., Subashchandrabose, S., Suresh, M., Ramesh Babu, N., 2017, FT-IR, FT-Raman and UV-Visible
Spectral analysis on (E)-N’-(thiophene-2-ylmethylene)
Nicotinohydrazide, Archives in Chemical Research, 1 (2:7) 1-14, https://doi.org/10.21767/2572-4657.100007.[36] Sathyanarayanan, D.N., 2004, Vibrational Spectroscopy theory and applications, New Age International Publishers, New Delhi, 2004, 446-447.
[37] Roeges, N.P.G., 1994, A Guide to the complete interpretation of Infrared Spectra of Organic structure, Wiley, New York.
[38] Barthes, M., De Nunzio, G., &Ribet, M., 1996, Polarons or proton transfer in chains of peptide groups? Synthetic Metals, 76(1-3), 337–340. https://doi.org/10.1016/0379-6779(95)03484-2.
[39] James, C., Ravikumar, C., Sundius, T., Krishnakumar, V.,
Kesavamoorthy, R., Jayakumar, V.S., & Hubert Joe, I., 2008,
FT-Raman and FTIR spectra, normal coordinate analysis and ab
initio computations of (2-methylphenoxy)acetic acid dimer. Vib. Spectrosco, 47(1), 10–20. https://doi.org/10.1016/j.vibspec.2008.01.006.[40] Singh, D.K., Srivastava, S.K., Ojha, A.K., &Asthana, B.P, 2008, Vibrational study of thiophene and its solvation in two polar
solvents, DMSO and methanol by Raman spectroscopy combined with ab initio and DFT calculations, J. Mol. Struct, 892(1-3), 384–391. https://doi.org/10.1016/j.molstruc.2008.06.008.[41] Fleming, G.D., Koch, R., & Campos Vallete, M.M, 2006,
Theoretical study of the syn and anti thiophene-2-aldehyde
conformers using density functional theory and normal coordinate analysis, Spectrochim. Acta A, 65(3-4), 935–945. https://doi.org/10.1016/j.saa.2006.01.038.[42] Badawi, H.M., 2009, Structural stability, C–N internal rotations and vibrational spectral analysis of non-planar phenylurea and phenylthiourea, Spectrochim. Acta A, 72(3), 523–527, https://doi.org/10.1016/j.saa.2008.10.042.
[43] Lorenc, J. (2012). Dimeric structure and hydrogen bonds in 2-N-ethylamino-5-metyl-4-nitro-pyridine studied by XRD, IR and Raman methods and DFT calculations, Vib. Spectrosc. 61, 112–123. https://doi.org/10.1016/j.vibspec.2012.03.006.
[44] Socrates, G., 1980, Infrared Characteristic Group Frequencies, John Wiley and Sons Ltd, New York.
[45] Subashchandrabose, S., Meganathan, C., Erdoğdu, Y., Saleem, H., Jajkumar, C., &Latha, P., 2013, Vibrational and conformational analysis on-N1-N2-bis ((pyridine-4-yl) methylene) benzene-1, 2-diamine, J. Mol. Struct, 1042, 37–44. https://doi.org/10.1016/j.molstruc.2013.03.034.
[46] Silverstein, M. Basseller, C.G., Morill, C, 1981, Spectrometric identification of organic compoundâ€, John Wiley; Network.
[47] Lorenc, J., 2012, Dimeric structure and hydrogen bonds in 2-N-ethylamino-5-metyl-4-nitro-pyridine studied by XRD, IR and Raman methods and DFT calculations, Vib. Spectrosc, 61, 112–123. https://doi.org/10.1016/j.vibspec.2012.03.006.
[48] Ramesh Babu, N., Subashchandrabose, S., Syed Ali Padusha, M., Saleem, H., &ErdoÄŸdu, Y., 2014, Synthesis and spectral
characterization of hydrazone derivative of furfural using
experimental and DFT methods. SpectrochimicaActa A, 120, 314–322. https://doi.org/10.1016/j.saa.2013.09.089.[49] Gorelsky, S.I., 2013, SWizard Program Revision 4.5, University of Ottawa, Ottawa, Canada.
[50] Chamberlain, N.F., 1974, the Practice of NMR Spectroscopy with Spectra-Structure Correlations for Hydrogen-1, Plenum Press.
[51] Andraud, C., Brotin, T., Garcia, C., Pelle, F., Goldner, P., Bigot, B., & Collet, A., 1994, Theoretical and experimental investigations of the nonlinear optical properties of vanillin, polyenovanillin, and bisvanillin derivatives. J. Am. chem. Soc. 116(5), 2094–2102. https://doi.org/10.1021/ja00084a055.
[52] Geskin, V.M., Lambert, C., &Brédas, J.L., 2003, Origin of High Second- and Third-Order Nonlinear Optical Response in
Ammonio/BoratoDiphenylpolyene Zwitterions: the Remarkable Role of Polarized Aromatic Groups, J. Am. Chem. Soc. 125(50), 15651–15658. https://doi.org/10.1021/ja035862p.[53] Liu, J., Chen, Z., & Yuan, S., 2005, Study on the prediction of
visible absorption maxima of azobenzene compounds, J. Zhejiang Univ. Sci. 6B(6), 584–589. https://doi.org/10.1631/jzus.2005.B0584.[54] James, C., Raj, A.A., Reghunathan, R., Jayakumar, V.S., & Joe, I.H., 2006, Structural conformation and vibrational spectroscopic studies of 2,6-bis(p-N,N-dimethyl benzylidene) cyclohexanone
using density functional theory, J. Raman Spectrosc. 37(12), 1381–1392. https://doi.org/10.1002/jrs.1554.[55] Liu, J.N., Chen, Z.R., & Yuan, S.F., 2005, Study on the prediction of visible absorption maxima of azobenzene compounds. Journal of Zhejiang University. Science. B, 6(6), 584.https://doi.org/10.1631/jzus.2005.B0584.
[56] Kohn, W., Becke, A.D., & Parr, R.G., 1996, Density Functional Theory of Electronic Structure, J. Phys. Chem. 100(31), 12974–12980. https://doi.org/10.1021/jp960669l.
[57] Parr, R.G., & Pearson, R.G., 1983, Absolute hardness: companion parameter to absolute electronegativity, J. Am. Chem. Soc. 105(26), 7512–7516. https://doi.org/10.1021/ja00364a005.
[58] Politzer, P., & Abu-Awwad, F., 1998, A comparative analysis of Hartree-Fock and Kohn-Sham orbital energies, Chem. Acc. 99(2), 83–87. https://doi.org/10.1007/s002140050307.
[59] Gunasekaran, S., Kumaresan, S., Arunbalaji, R., Anand, G., &Srinivasan, S., 2008, Density functional theory study of
vibrational spectra, and assignment of fundamental modes of
dacarbazine, J. Chem. Sci. 120(3), 315–324. https://doi.org/10.1007/s12039-008-0054-8.[60] Bevan Ott, J., Boerio-Goates, J., 2000, Calculations from Statical Thermodynamics, Academic Press.
Downloads
How to Cite
Received date: January 5, 2018
Accepted date: February 5, 2018
Published date: February 14, 2018