Research on Chemical Intermediates

, Volume 45, Issue 5, pp 2565–2586 | Cite as

Experimental and theoretical study of S-benzyl β-N-(-2-methyl-3-phenylallylidene)dithiocarbazate as anti-bacterial agent

  • Rayees A. BhatEmail author
  • D. Kumar


The NS based S-benzyl β-(N-2-methyl-3-phenylallylidene)dithiocarbazate (L) Schiff base was synthesized by 1:1 condensation method between S-benzyl dithiocarbazate and α-methyl-trans-cinnamaldehyde. The structure of the compound was elucidated by FT-IR, Mass, 13C-NMR, Raman, 1H-NMR, and UV–Vis both by spectroscopic and computational techniques. Its anti-bacterial activity is assayed against two commonly infection causing bacterial strains, namely gram-positive Staphylococcus aureus and gram-negative Escherichia coli. The results showed appreciable biological activity, and the activity increased with increase in concentration. Thermal stability of the ligand was carried by TGA up to 800 °C, and decomposes fully to give gaseous products. Theoretical investigation of (L) has been accomplished using the DFT-B3LYP quantum chemical method in combination with B3LYP exchange correlation functional. VEDA-4 (vibrational energy distribution analysis) software was employed for theoretical FT-IR spectrum analysis which yielded 114 fundamental vibrational modes along with a potential energy distribution percentage showing non-linearity of (L). Theoretically calculated parameters like UV–VIS, FT-IR, 1H-NMR, 13C-NMR, Raman, HOMO–LUMO energy gap and electrostatic potential were in conformity with calculated results.


Dithiocarbazate LanL2DZ PED% MEP Thermal 



The author (Rayees A. Bhat) thanks the UGC (University Grant Commission), New Delhi for the monetary support provided (UGC-MANF Ref. No. MANF-2015-17-JAM-49814).

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.


  1. 1.
    T. Curtius, K. Heidenreich, J. Prakt. Chem. 52, 454 (1895)CrossRefGoogle Scholar
  2. 2.
    S. Shrivastava, A. Kumar, Y. Pandey, S.N. Dikshit, Asian J. Chem. 21, 6228 (2009)Google Scholar
  3. 3.
    A. Husain, S.A.A. Nami, K.S. Siddiqi, J. Mol. Struct. 970, 117 (2010)CrossRefGoogle Scholar
  4. 4.
    S.K.S. Hazari, J. Kopf, D. Palit, S. Rakshit, D. Rehder, Inorg. Chim. Acta 362, 1343 (2009)CrossRefGoogle Scholar
  5. 5.
    A. Saxena, J.P. Tandon, Cancer Lett. 19, 73 (1983)CrossRefGoogle Scholar
  6. 6.
    K. Tampouris, S. Coco, A. Yannopoulos, S. Koinis, Polyhedron 26, 4269 (2007)CrossRefGoogle Scholar
  7. 7.
    P. Bera, C.-H. Kim, S.I. Seok, Solid State Sci. 12, 532 (2010)CrossRefGoogle Scholar
  8. 8.
    M. Singh, A.K. Pandey, R.J. Butcher, N.K. Singh, Polyhedron 28, 461 (2009)CrossRefGoogle Scholar
  9. 9.
    P. Bera, C.-H. Kim, S.I. Seok, Polyhedron 27, 3433 (2008)CrossRefGoogle Scholar
  10. 10.
    H.P. Zhou, D.M. Li, P. Wang, L.H. Cheng, Y.H. Gao, Y.M. Zhu, J.Y. Wu, Y.P. Tian, X.T. Tao, M.H. Jiang, H.K. Fun, J. Mol. Struct. 826, 205 (2007)CrossRefGoogle Scholar
  11. 11.
    J.J. Xia, J. Struct. Chem. 55, 130 (2014)CrossRefGoogle Scholar
  12. 12.
    A.B. Beshir, S.K. Guchhait, J.A. Gascón, G. Fenteany, Bioorg. Med. Chem. Lett. 18, 498 (2008)CrossRefGoogle Scholar
  13. 13.
    M. Yazdanbakhsh, R. Takjoo, Struct. Chem. 19, 895 (2008)CrossRefGoogle Scholar
  14. 14.
    M.H.S.A. Hamid, M. Akbar Ali, A.H. Mirza, P.V. Bernhardt, B. Moubaraki, K.S. Murray, Inorg. Chim. Acta. 362, 3648 (2009)CrossRefGoogle Scholar
  15. 15.
    Y.T. Liu, G.D. Lian, D.W. Yin, B.J. Su, Spectrochim. Acta Part A 100, 131 (2013)CrossRefGoogle Scholar
  16. 16.
    R.A. Bhat, D. Kumar, M.A. Malla, S.U. Bhat, M.S. Khan, O. Manzoor, A. Srivastava, R.A. Naikoo, M. Mohsin, M.A. Mir, J. Mol. Struct. 1156, 280 (2018)CrossRefGoogle Scholar
  17. 17.
    M.H.S.A. Hamid, M.A. Ali, A.H. Mirza, A.H. Mirza, P.V. Bernhardt, B. Moubaraki, K.S. Murray, Inorg. Chem. Acta. 362, 3648 (2009)CrossRefGoogle Scholar
  18. 18.
    A.D. Becke, Phys. Rev. A 38(6), 3098 (1988)CrossRefGoogle Scholar
  19. 19.
    C. Lee, W. Yang, R.G. Parr, Phys. Rev. B. 37, 785 (1988)CrossRefGoogle Scholar
  20. 20.
    M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Asegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, 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. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 09, Revision E.01 (Gaussian Inc, Pittsburgh, 2009)Google Scholar
  21. 21.
    R.S. Mulliken, J. Chem. Phys. 23, 1841 (1955)CrossRefGoogle Scholar
  22. 22.
    K. Fukui, T. Yonezawa, H. Shingu, J. Chem. Phys. 20, 1653 (1952)CrossRefGoogle Scholar
  23. 23.
    B.H. Stuart, Infrared Spectroscopy: Fundamentals and Applications (Wiley, Chichester, 2004)CrossRefGoogle Scholar
  24. 24.
    G. Socrates, Infrared and Raman Characteristic group Frequencies, Tables and Charts, 3rd edn. (Wiley, Chichester, 2001)Google Scholar
  25. 25.
    I. Fleming, Frontier Orbitals and Organic Chemical Reactions (Wiley, New York, 1976)Google Scholar
  26. 26.
    T. Kavitha, G. Pasupathi, M.K. Marchewka, G. Anbalagan, N. Kanagathara, J. Mol. Struct. 1143, 378 (2017)CrossRefGoogle Scholar
  27. 27.
    J.P. Foster, F. Weinhold, J. Am. Chem. Soc. 102, 7211 (1980)CrossRefGoogle Scholar
  28. 28.
    M. Snhelatha, C. Ravikumar, I. Hubertjoe, N. Sekar, V.S. Jayakumar, Spectrochim. Acta. A 72, 654 (2009)CrossRefGoogle Scholar
  29. 29.
    A.W. Bauer, W.M. Kirby, J.C. Sherries, M. Turckp, Am. J. Clin. Pathol. 45, 493 (1966)CrossRefGoogle Scholar
  30. 30.
    Analysis and presentation of cumulative antimicrobial susceptiblity test data; Approved Guidelines,-Fourth edition. CLSI document M39-4A, P.A. Wayne: Clinical and Laboratory Standards Institute (2014)Google Scholar
  31. 31.
    J. Xiaoxiao, W. Jiangtao, B. Jie, J. Chem. Eng. Chin. Univ. 04, 645–650 (2010)Google Scholar
  32. 32.
    J. Parekh, P. Inamdhar, R. Nair, S. Baluja, S. Chanda, J. Serb. Chem. Soc. 70, 1155 (2005)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Centre of Research for Chemical Sciences, Government Model Science CollegeJiwaji UniversityGwaliorIndia

Personalised recommendations