JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 2 (2018): Journal of the Chilean Chemical Society
Original Research Papers

MICROWAVE ASSISTED SYNTHESIS, SPECTRAL CORRELATION AND ANTIMICROBIAL EVALUATION OF SOME ARYL IMINES

PDF
  • S. Pazhinivel Sakthinathan,
  • Ramamoorthy Suresh,
  • Dakshnamoorthy Kamalakkannan,
  • Veerandiran Mala,
  • Kaliyan Sathiyamoorthi,
  • Ganesan Vanangamudi,
  • Ganesamoorthy Thirunarayanan
S. Pazhinivel Sakthinathan
PG & Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram-608102
Ramamoorthy Suresh
PG & Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram-608102
Dakshnamoorthy Kamalakkannan
PG & Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram-608102
Veerandiran Mala
PG & Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram-608102
Kaliyan Sathiyamoorthi
PG & Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram-608102
Ganesan Vanangamudi
PG & Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram-608102
Ganesamoorthy Thirunarayanan
Department of Chemistry, Annamalai University, Annamalainagar-608002
Published June 25, 2018
Keywords
  • Solvent-free synthesis,
  • SiO2-H3PO4,
  • Aryl imines,
  • IR and NMR spectra,
  • Spectral correlation study,
  • Antimicrobial activities
    • ...More
    Less
How to Cite
Sakthinathan, S. P., Suresh, R., Kamalakkannan, D., Mala, V., Sathiyamoorthi, K., Vanangamudi, G., & Thirunarayanan, G. (2018). MICROWAVE ASSISTED SYNTHESIS, SPECTRAL CORRELATION AND ANTIMICROBIAL EVALUATION OF SOME ARYL IMINES. Journal of the Chilean Chemical Society, 63(2). Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/669

Copyright (c) 2018 Journal of the Chilean Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.

Abstract

A series of aryl imines have been synthesized by SiO2-H3PO4 catalyzed microwave assisted condensation of amine and aldehyde under solvent-free conditions. The yield of the imines has been found to be more than 80%. The purity of all imines has been checked using their physical constants and spectral data as published earlier in literature. The UV λmax(nm), infrared νC=N(cm-1), NMR δ(ppm) of C-H and C=N spectral data have been correlated with Hammett substituent constants and F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituents on the above spectral data has been studied. The antimicrobial activities of all imines have been studied using Bauer-Kirby method.

PDF

References

  1. A. S. Shawali, N. M. S. Harb, K. O. Badahdah, J. Heterocycl.Chem. 22, 1397 (1985).
  2. M. Mustapha, B. R. Thorat, S.Sawant, R. G. Atram, R. Yamgar, J. Chem. Pharm. Res. 3(4), 5 (2011).
  3. K. C. Gupta, A. K. Sutar. Co. ord. Chem. Rev. 252, 1420 (2008).
  4. M. Yuan, F. Zhao, W. Zhang, Z. M. Wang, S. Gao, Inorg. Chem. 46, 11235 (2007).
  5. H. Fukuda, K. Amimoto, H. Koyama, T. Kawato, Tetrahedron Lett. 50, 5376 (2009).
  6. Y.C. Liu, C.Y. Yang, Inorg. Chem. Commun., 12, 704 (2009).
  7. A. C. W. Leung, M. J. Mac Lachlan, J. Inorg. Organomet.Polym.Mater. 17, 57 (2007).
  8. W. Zishen, L. Zhiping, Y. Zhenhuan Transit. Met. Chem. 18 291 (1993).
  9. K. Nejati, Z. Rezvani, B. Massoumi, Dyes Pigment. 75 653 (2007).
  10. E. Naderi, A. H. Jafari, M. Ehteshamzadeh, M.G. Hosseini, Met. Chem. Phys. 115 852 (2006).
  11. D. Sriram, P. Yogeeswari, N.S. Myneedu, V. Saraswati, Bioorg. Med. Chem. Lett. 16, 2127 (2006).
  12. V. Stilinovic, D. Cincic, B. Kaitner, Acta. Chim.Slov. 55, 874 (2008).
  13. V. Tiwari, J. Meshram, P. Ali, Der. Pharm. Chim. 2, 187 (2010).
  14. J.J. Bhatt, B.R. Shah, H.P. Shah, P.B. Trivedi, N.K. Undavia, N.C. Desai, Indian. J. Chem. 33B, 189 (1994).
  15. A. A. Bakibaev, V. K. Gorshkova, O. V. Arbit, V. D. Filimonov, A. S. Saratikov, Pharm. Chem. J. 31, 53 (1997).
  16. R.B. Patel, P.S. Desai, K.R. Desai, K.H. Chikhalia, Indian J. Chem. 45B, 773 (2006).
  17. S. Kantevari, T. Yempala, P. Yogeswari, D. Sriram, B. Sridhar, Bioorg. Med. Chem. Lett. 15, 4316 (2011).
  18. A. Kundu, N. A. Shakil, D. B. Saxena, J. Pankaj Kumar and S. Walia, J. Env. Sci. Health. 44B 428 (2000).
  19. R. Yadav, S.D. Srivastava, S.K. Srivastava, Indian. J. Chem. 44B, 1262 (2005).
  20. R. T. McBurney, P. C. Fernando, J. C. Walton, RSC Adv. 12, 1264 (2012).
  21. M. Adib, E. Sheibani, H. R. Bijanzadeh, L. G. Zhu, Tetrahedron. 64, 10681 (2008).
  22. A. K. Chakraborti, S. Bhagat, S. Rudrawar, Tetrahedron Lett. 45, 7641 (2004).
  23. M. Movrin, D. Maysinger, Pharmaize, 34, 535 (1979).
  24. J. Barluenga, J. A. Agustin, F. Aznar, C. Valdes, J. Am. Chem. Soc. 131, 4031 (2009).
  25. D. Bandyophayay, S. Mukherjee, R. R. Rodriguez, B. K. Banik. Molecules, 15, 4207 (2010).
  26. S. K. Samanta, I.Kylanlathi and J. Y. Kauhaluoma, Bioorg. Med. Chem. Lett. 15, 3717 (2005).
  27. A. Lumbroso, F. Chevillier, I. Beaudet, T. Bessan, E. L. Grognet, Tetrahedron. 65 9180 (2009).
  28. H. J. conn, “A Handbook on the Nature and Uses of the Dyes Employed in the Biological Laboratory” SIXTH EDITION, THE WILLIAMS & WILKINS COMPANY, Baltimore 2, (1953) Maryland, USA.
  29. B. D. Mather, K. Viswanathan, K. M. Miller, T. E. Long., Prog. Polym. Sci. 31, 487 (2006).
  30. S. F. Martin, Pure Appl. Chem. 81, 195(2009).
  31. A. C. Dash, B. Dash, D. Panda, J. Org. Chem. 50, 2905 (1985).
  32. J. H. Xie, S. F. Zhu, Q. L. Zhou, Chem. Rev. 111, 1731(2011).
  33. S. E. Denmark, G. L. Beutner, Angew. Chem. Int. Ed. 47, 1560 (2008).
  34. A. Suares, C. W. Downey, G. C. Fu, J. Am. Chem. Soc. 127, 11244 (2005).
  35. S. France, M. H. Shah, A. Weatherwax, H. Wack, J. P. Roth, T. Lectka, J. Am. Chem. Soc. 127, 1206 (2005).
  36. W. Chang, B. J. Ahn, J. Ind. Engg. Chem. 10, 690 (2004).
  37. M. Abid, M. Savolainen, S.Landge, J. Hu, G. K. Suryaprakash, G. A. Olah, B. Torok, J. Fluo. Chem. 128, 587 (2007).
  38. D. A. Barr, G. Donegn, R. Grigg, J. Chem. Soc., Perkin Trans. 1, 1550 (1989).
  39. L. Blackburn, R. J. K. Taylor, Org. Lett. 3, 1637 (2001).
  40. M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, Res. Chem. Inter. med. 33, 541 (2007).
  41. R. S. Varama, Green Chem. (1999) 43.
  42. G. Dutheuil, S. C. Bonnaire, X. Pannecoucke, Angew. Chem. Int. Ed. Engl .46, 1290 (2007).
  43. B. H. Lipshutz, H. Shimizu, Angew. Chem. Int. Ed. 43 2228 (2004).
  44. E. Ali, M. R. N. Jamal, Efficient synthesis of imines by MCM-41-SO3H nanaocatalyst. No. A006, 14th international Conference on synthetic organic chemistry, (ESCOC-14), 1 (2010).
  45. A. Hasaninejad, A. Zare, H. Sharghi, M. Shekouhy, Arkicov. 11, 64 (2008).
  46. H. Zhanag, S. Syed, C. F. Barbas, Org. Lett. 12,708 (2010).
  47. C. M. Bode, A. Ting, S. E. A. Schaus, Tetrahedron. 62, 11499 (2006).
  48. M. A. Vazquez, M. Landa, L. Reyes, M. J. Tamariz, D. Francisco, Synth. Commun. 34, 2705 (2004).
  49. M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph series, ACS, Washington, DC, (1990).
  50. S. M. Landge, V. Atanassova, M.Thimmaiah, B. Torok, Tetrahedron Lett. 48, 5161 (2007).
  51. G. Thirunarayanan, .Iup. J. Chem. 3(4), 35 (2010).
  52. A. W. Bauer, W. M. M. Kirby, J. C Sherris, M. Truck, .Am. J. Clin. Pathol. 45, 493 (1996).
  53. K. Sathiyamoorthi, V. Mala, S.P. Sakthinathan, D. Kamalakkannan, R. Suresh, G. Vanangamudi , G. Thirunarayanan Spectrochimica Acta, 112A, 245 (2013).
  54. (a). S. P. Sakthinathan, G. Vanangamudi, G. Thirunarayanan Spectrochimica Acta 95A, 693 (2012). (b). G. Thirunarayanan, G. Vanangamudi, Spectrochimica Acta 81A, 390 (2011). (c) G. Thirunarayanan, M. Gopalakrishnan, G.Vanangamudi, Spectrochimica Acta 67(A), 1106 (2007).
  55. B.Zˇ. Jovanovic´, A.D. Marinkovic´, F.H. Assaleh, J. Csana´d, J. Mol. Str. 744 (2005).
  56. S. Ž. Drmanić, A. D. Marinković, J. B. Nikolić, B. Jovanović, J. Serb. Chem. Soci. 77, 1 (2012).
  57. C. G. Swain, E. C. Lupton, J.Amer. Chem. Soc., 90, 4328 (1968).

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP