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Growth, spectral and thermal characterization of vanillin semicarbazone (VNSC) single crystals

Journal of Thermal Analysis and Calorimetry volume 111, pages 575–581 (2013)Cite this article

Abstract

Vanillin semicarbazone (VNSC) has been synthesized from 4-hydroxy 3-methoxy benzaldehyde and semicarbazide hydrochloride using sodium acetate as catalyst. Good quality single crystals of VNSC were successfully grown by slow evaporation method at room temperature using DMF as solvent. The grown crystals have been characterized using melting point, elemental analysis, FT-IR, UV–Visible, 1H NMR, 13C NMR, and X-Ray diffraction analysis. The compound crystallizes into an orthorhombic Pca21 space group. Intermolecular hydrogen bonding interactions facilitate unit cell packing in the crystal lattice. The UV–Visible spectrum confirmed the transparency of the compound between the wavelengths 420 and 1,200 nm, which is characteristic to property of an NLO material. The thermal decomposition of the compound under static air atmosphere was investigated by simultaneous TG/DTG at a heating rate of 10 °C/min.

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References

  1. Pal I, Dutta S, Basuli F, Goverdhan S, Peng S-M, Lee G-H, Battacharya S. Unprecedented chemical transformation of semicarbazones mediated by Wilkinson’s Catalyst. Inorg Chem. 2003;42:4338–45.

    Article  CAS  Google Scholar 

  2. Cocco MT, Congiu C, Onnis V, Pellerano ML, Logu AD. Synthesis and Antimycobacterial activity of new S-alkylisothiosemicarbazone derivatives. Bioorg Med Chem. 2002;10:501–6.

    Article  CAS  Google Scholar 

  3. Scovill JP, Klaymam DL, Lambros C, Childs GE, Notsch JD. 2-Acetylpyridine thiosemicarbazones. 9. Derivatives of 2-acetylpyridine 1-oxide as potential antimalarial agents. J Med Chem. 1984;27:87–91.

    Article  CAS  Google Scholar 

  4. Arguelles MCR-, Silva ECL-, Sanmartin J, Pelagatti P, Zani F. Copper complexes of imidazole-2-, pyrrole-2- and indol-3-carbaldehyde thiosemicarbazones: inhibitory activity against fungi and bacteria. J Inorg Biochem 2005;99:2231–2239.

    Google Scholar 

  5. Hu W, Zhou W, Xia C, Wen X. Synthesis and anticancer activity of thiosemicarbazones. Bioorg Med Chem Lett. 2006;16:2213–8.

    Article  CAS  Google Scholar 

  6. Janarthanan S, Samuel RS, Rajan YC, Pandi S. Growth, spectral and thermal characterization of the NLO crystal: semicarbazone of DL-camphor (SDLC). J Therm Anal Calorim. doi:10.1007/s10973-011-1632-4.

  7. Janarthanan S, Rajan YC, Umarani PR, Jayaraman D, Premanand D, Pandi S. Synthesis, growth, optical and thermal properties of a new organic crystal semicarbazone of p-anisaldehyde (SPAS). Indian J Sci Technol. 2010;3:885–9.

    CAS  Google Scholar 

  8. Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR. Vogels text book of practical organic chemistry, 5th ed. London: English Language Book Society: Chapman and Hall; 1996.

  9. Dimmock JR, Baker GB. Anticonvulsant activities of 4-bromobenzaldehyde semicarbazone. Epilepsia. 1994;35:648–65.

    Article  CAS  Google Scholar 

  10. Torres EL-, Abram U. Rhenium complexes with triazine derivatives formed from semicarbazones and thiosemicarbazones. Inorg Chem. 2008;47:2890–6.

    Article  Google Scholar 

  11. Lee PF, Yang C-T, Fan D, Vittal JJ, Ranford JD. Synthesis, characterization and physicochemical properties of copper(II) complexes containing salicylaldehyde semicarbazone. Polyhedron. 2003;22:2781–6.

    Article  CAS  Google Scholar 

  12. Leovac VM, Jovanoic LS, Divjakovic V, Pevec A, Leban I, Armbruster T. Transition metal complexes with thiosemicarbazide-based ligands. Part LIV. Nickel(II) complexes with pyridoxal semi-(PLSC) and thiosemicarbazone (PLTSC). Crystal and molecular structure of [Ni(PLSC)(H2O)3](NO3)2 and [Ni(PLTSC-H)py]NO3. Polyhedron. 2007;26:49–58.

    Article  CAS  Google Scholar 

  13. Radovanovic BCS-, Milic BL. Thermal decomposition of 5-nitro-2-furaldehyde semicarbazone. J Therm Anal Calorim 1987;32:485–490.

    Google Scholar 

  14. Altomare A, Cascarano G, Giacovazzo C, Guagliardi A. Completion and refinement of crystal structures with SIR92. J Appl Cryst. 1993;26:343–50.

    Article  Google Scholar 

  15. Sheldrick GM. SHELXL97: program for the refinement of crystal structures. Germany: University of Gottingen; 1997.

    Google Scholar 

  16. Brandenburg K. DIAMOND version 3.1d. Crystal impact GbR. Bonn: Germany; 2006.

  17. Panicker CY,Varghese HT, Philip D, Nogueira HIS, Castkov K. Raman, IR and SERS spectra of methyl(2-methyl-4,6-dinitrophenylsulfanyl)ethanoate. Spectrochim Acta 2007;67:1313–1320.

    Google Scholar 

  18. Janarthanan S, Samuel RS, Rajan YC, Pandi S. Growth, spectral and thermal characterization of semicarbazone of p-hydroxy acetophenone (SPHA). J Therm Anal Calorim. doi:10.1007/s10973-011-1627-1.

  19. Janarthanan S, Samuel RS, Rajan YC, Umarani PR, Pandi S. Spectral and thermal characterization of grown organic single crystal semicarbazone of p-hydroxy benzaldehyde (SPHB). J Therm Anal Calorim. doi:10.1007/s10973-011-1437-5.

  20. Manivannan S, Dhanuskodi S. Growth and characterization of a new organic nonlinear optical crystal: semicarbazone of p-dimethylamino benzaldehyde. J Cryst Growth. 2003;257:305–8.

    Article  CAS  Google Scholar 

  21. Madhurambal G, Ramasamy P, Anbusrinivasan P, Vasudevan G, Kavitha S, Mojumdar SC. Growth and characterization studies of 2-bromo-4-chloroacetophenone (BCAP) crystals. J Therm Anal Calorim. 2008;94:59–62.

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are grateful to the authorities of the SAIF, Cochin University of Science and Technology, and SAIF, IIT Madras, Chennai, for providing the instrumental facilities. Two of the authors are thankful to University of Kerala for the financial support.

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Authors and Affiliations

  1. Department of Chemistry, S. N. College, Kollam, 691001, Kerala, India

    P. S. Binil, M. R. Anoop & K. R. Jisha

  2. Department of Chemistry, S. N. College, Chempazhanthy, 695587, Kerala, India

    S. Suma

  3. Department of Chemistry, M. G. College, Thiruvananthapuram, 695004, Kerala, India

    M. R. Sudarsanakumar

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  1. P. S. Binil
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  2. M. R. Anoop
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  3. K. R. Jisha
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Correspondence to S. Suma.

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Binil, P.S., Anoop, M.R., Jisha, K.R. et al. Growth, spectral and thermal characterization of vanillin semicarbazone (VNSC) single crystals. J Therm Anal Calorim 111, 575–581 (2013). https://doi.org/10.1007/s10973-012-2228-3

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Keywords

  • Semicarbazone of vanillin
  • X-ray diffraction
  • NMR
  • Thermal studies