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Vol. 33 No. 11 (2021): Vol 33 Issue 11, 2021

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FT-IR, FT-Raman, NMR Spectroscopic and DFT Quantum Chemical Investigations of 6-Methylcoumarin

https://doi.org/10.14233/ajchem.2021.23147
R. Kanimozhi
Centre for Research and Evaluation, Bharathiar University, Coimbatore-641046, India
V. Arjunan
Department of Chemistry, Kanchi Mamunivar Centre for Post-Graduate Studies, Puducherry-605008, India ; Department of Chemistry, Rajiv Gandhi Arts & Science College, Thavalakuppam, Puducherry-605007, India

Corresponding Author(s) : V. Arjunan

varjunftir@yahoo.com

Asian Journal of Chemistry, Vol. 33 No. 11 (2021): Vol 33 Issue 11, 2021

Abstract

The structural geometry, electronic and reactivity characteristics, vibrational assignments and the fundamental modes of 6-methylcoumarin have been carried out. The effect of methyl group on the pyrone skeletal vibrations was also discussed. The experimental vibrational frequencies were compared with the wavenumbers obtained theoretically from the B3LYP method employing the high level 6-311++G** and cc-pVTZ basis sets. Frontier molecular orbital (FMO) energy and the LUMO-HOMO energy gap was measured. The atomic charges and the bond properties were examined by natural bond orbital analysis. The hydrogen and carbon environment were examined by NMR spectra. The nuclophilic, electrophilic and free radical attacking sites of 6-methylcoumarin were also analyzed.

Keywords

Methylcoumarin FT-Raman NMR DFT Reactivity descriptors
Kanimozhi, R., & Arjunan, V. (2021). FT-IR, FT-Raman, NMR Spectroscopic and DFT Quantum Chemical Investigations of 6-Methylcoumarin. Asian Journal of Chemistry, 33(11), 2715–2722. https://doi.org/10.14233/ajchem.2021.23147
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References
  1. C.S. Francisco, C.S. Francisco, A.F. Constantino, Á.C. Neto and V. Lacerda Jr., Curr. Org. Chem., 23, 2722 (2019); https://doi.org/10.2174/1385272823666191121150047
  2. F. Annunziata, C. Pinna, S. Dallavalle, L. Tamborini and A. Pinto, Int. J. Mol. Sci., 21, 4618 (2020); https://doi.org/10.3390/ijms21134618
  3. A. Stefanachi, F. Leonetti, L. Pisani, M. Catto and A. Carotti, Molecules, 23, 250 (2018); https://doi.org/10.3390/molecules23020250
  4. L.C. Di Stasi, Molecules, 26, 422 (2021); https://doi.org/10.3390/molecules26020422
  5. C.T. Supuran, J. Enzym. Inhibit. Med. Chem., 35, 1462 (2020); https://doi.org/10.1080/14756366.2020.1788009
  6. A. Bouhaoui, M. Eddahmi, M. Dib, M. Khouili, A. Aires, M. Catto and L. Bouissane, ChemistrySelect, 6, 5848 (2021); https://doi.org/10.1002/slct.202101346
  7. K.N. Venugopala, Rashmi and B. Odhav, BioMed Res. Int., 2013, 963248 (2013); https://doi.org/10.1155/2013/963248
  8. H. Chang, M. Shi, Y.-N. Sun and J.-Q. Jiang, Chin. J. Polym. Sci., 33, 1086 (2015); https://doi.org/10.1007/s10118-015-1657-4
  9. V. Arjunan, S. Sakiladevi, M.K. Marchewka and S. Mohan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 109, 79 (2013); https://doi.org/10.1016/j.saa.2013.01.100
  10. V. Arjunan, R. Santhanam, S. Sakiladevi, M.K. Marchewka and S. Mohan, J. Mol. Struct., 1037, 305 (2013); https://doi.org/10.1016/j.molstruc.2013.01.014
  11. A. Stamm, K. Schwing and M. Gerhards, J. Chem. Phys., 141, 194304 (2014); https://doi.org/10.1063/1.4900893
  12. M. Arivazhagan, R. Kavitha and V.P. Subhasini, Spectrochim. Acta A Mol. Biomol. Spectrosc., 130, 502 (2014); https://doi.org/10.1016/j.saa.2014.04.001
  13. N. Udaya Sri, K. Chaitanya, M.V.S. Prasad, V. Veeraiah and A. Veeraiah, Spectrochim. Acta A Mol. Biomol. Spectrosc., 97, 728 (2012); https://doi.org/10.1016/j.saa.2012.07.055
  14. J. Tonannavar, J. Yenagi, V. Sortur, V.B. Jadhav and M.V. Kulkarni, Spectrochim. Acta A Mol. Biomol. Spectrosc., 77, 351 (2010); https://doi.org/10.1016/j.saa.2010.03.013
  15. A. Ramoji, J. Yenagi, J. Tonannavar, V.B. Jadhav and M.V. Kulkarni, Spectrochim. Acta A Mol. Biomol. Spectrosc., 77, 1039 (2010); https://doi.org/10.1016/j.saa.2010.08.070
  16. I. Sidir, Y.G. Sidir, M. Kumalar and E. Tasal, J. Mol. Struct., 964, 134 (2010); https://doi.org/10.1016/j.molstruc.2009.11.023
  17. A.N. Castro, L.R. Almeida, M.M. Anjos, G.R. Oliveira, H.B. Napolitano, C. Valverde and B. Baseia, Chem. Phys. Lett., 653, 122 (2016); https://doi.org/10.1016/j.cplett.2016.04.070
  18. F. Zhang, H. Zhang, D. Fang and Q. Liu, Spectrochim. Acta A Mol. Biomol. Spectrosc., 71, 710 (2008); https://doi.org/10.1016/j.saa.2008.01.035
  19. V. Sortur, J. Yenagi, J. Tonannavar, V.B. Jadhav and M.V. Kulkarni, Spectrochim. Acta A Mol. Biomol. Spectrosc., 64, 301 (2006); https://doi.org/10.1016/j.saa.2005.07.024
  20. R.O. Juvonen, M. Kuusisto, C. Fohrgrup, M.H. Pitkanen, T.J. Nevalainen, S. Auriola, H. Raunio, M. Pasanen and O.T. Pentikainen, Xenobiotica, 46, 14 (2015); https://doi.org/10.3109/00498254.2015.1048327
  21. A.R. Hernández, L.F. Ospina and D.M. Aragón, Biomed. Chromatogr., 29, 176 (2015); https://doi.org/10.1002/bmc.3253
  22. J.-S. Lan, L.-F. Pan, S.-S. Xie, X.-B. Wang and L.-Y. Kong, Med. Chem. Commun., 6, 592 (2015); https://doi.org/10.1039/C4MD00437J
  23. M.J. Matos, F. Pérez-Cruz, S. Vazquez-Rodriguez, E. Uriarte, L. Santana, F. Borges and C. Olea-Azar, Bioorg. Med. Chem., 21, 3900 (2013); https://doi.org/10.1016/j.bmc.2013.04.015
  24. B.C. Pemberton, A. Ugrinov and J. Sivaguru, J. Photochem. Photobiol. Chem., 255, 10 (2013); https://doi.org/10.1016/j.jphotochem.2013.01.005
  25. J.-F. Nie, H.-L. Wu, S.-H. Zhu, Q.-J. Han, H.-Y. Fu, S.-F. Li and R.-Q. Yu, Talanta, 75, 1260 (2008); https://doi.org/10.1016/j.talanta.2008.01.026
  26. P. Hohenberg and W. Kohn, Phys. Rev. B, 136(3B), 864 (1964); https://doi.org/10.1103/PhysRev.136.B864
  27. A.D. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
  28. A.D. Becke, Phys. Rev. A, 38, 3098 (1988); https://doi.org/10.1103/PhysRevA.38.3098
  29. C. Lee, W. Yang and R.G. Parr, Phys. Rev. B Condens. Matter, 37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785
  30. 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, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian, Inc., Wallingford, CT (2009).
  31. J.S. Murray and K. Sen, Molecular Electrostatic Potentials, Concepts and Applications, Elsevier, Amsterdam (1996).
  32. R.I. Dennington, T. Keith and J. Millam, GaussView, Version 5.0.8, Semichem. Inc., Shawnee Mission, KS (2008).
  33. J.P. Foster and F. Weinhold, J. Am. Chem. Soc., 102, 7211 (1980); https://doi.org/10.1021/ja00544a007
  34. A.E. Reed, R.B. Weinstock and F. Weinhold, J. Chem. Phys., 83, 735 (1985); https://doi.org/10.1063/1.449486
  35. A.E. Reed and F. Weinhold, J. Chem. Phys., 78, 4066 (1983); https://doi.org/10.1063/1.445134
  36. R. Ditchfield, J. Chem. Phys., 56, 5688 (1972); https://doi.org/10.1063/1.1677088
  37. K. Wolinski, J.F. Hinton and P. Pulay, J. Am. Chem. Soc., 112, 8251 (1990); https://doi.org/10.1021/ja00179a005
  38. M.K. Kokila, A. Jain, Puttaraja, M.V. Kulkarni and N.C. Shivaprakash, Acta Crystallogr. C, 51, 2585 (1995); https://doi.org/10.1107/S0108270195006263
  39. Y. Yamada, M. Okamoto, H. Kikuzaki and N. Nakatani, Biosci. Biotechnol. Biochem., 61, 740 (1997); https://doi.org/10.1271/bbb.61.740
  40. H. Fuhrer, V.B. Kartha, K.L. Kidd, P.J. Kruger and H.H. Mantsch, Computer Program for Infrared and Spectrometry, Normal Coordinate Analysis, National Research Council, Ottawa, Canada, vol. 5 (1976).
  41. Y. Uesugi, M. Mizuno, A. Shimojima and H. Takahashi, J. Phys. Chem. A, 101, 268 (1997); https://doi.org/10.1021/jp9626881
  42. V. Krishnakumar and R.J. Xavier and J. Indian Pure Appl. Phys., 41, 597 (2003).
  43. M.K. Subramanian, P.M. Anbarasan and S. Manimegalai, Pramana- J. Phys., 74, 845 (2010); https://doi.org/10.1007/s12043-010-0104-x
  44. B.C. Smith, Infrared Spectral Interpretation: A Systematic Approach, CRC Press, Boca Raton, Florida (1998).
  45. G. Socrates, Infrared and Raman Characteristic Group Frequencies – Tables and Charts, John Wiley & Sons, Chichester, Ed.: 3 (2001).
  46. G. Varsanyi, Vibrational Spectra of Benzene Derivatives, Academic Press: NewYork (1969).
  47. N.P. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures, Wiley: New York (1994).
  48. N. Udaya Sri, K. Chaitanya, M.V.S. Prasad, V. Veeraiah and A. Veeraiah, Spectrochim. Acta A Mol. Biomol. Spectrosc., 97, 728 (2012); https://doi.org/10.1016/j.saa.2012.07.055
  49. V. Arjunan and S. Mohan, J. Mol. Struct., 892, 289 (2008); https://doi.org/10.1016/j.molstruc.2008.05.053
  50. V. Arjunan and S. Mohan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 72, 436 (2009); https://doi.org/10.1016/j.saa.2008.10.017
  51. J.O. Jensen, A. Banerjee, C.N. Merrow, D. Zeroka and J. Michael Lochner, J. Mol. Struct. THEOCHEM, 531, 323 (2000); https://doi.org/10.1016/S0166-1280(00)00465-6
  52. V. Arjunan, P. Ravindran, T. Rani and S. Mohan, J. Mol. Struct., 988, 91 (2011); https://doi.org/10.1016/j.molstruc.2010.12.032
  53. R.M. Silverstein, G.C. Bassler and T.C. Morrill, Spectrometric Identification of Organic Compounds, Wiley: New York, Ed.: 5, p. 245 (1991).
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