PHASE TRANSFER CATALYTIC SYNTHESIS, SPECTRAL CHARACTERIZATION AND ANTIMICROBIAL EVALUATION OF 2-(PHENYLSELENO) ETHANOIC ACID AND 3-(PHENYL SELENO) PROPANOIC ACID.

  • Department of Chemistry, ITM University, Gwalior.
  • SOS in Chemistry, Jiwaji University, Gwalior.
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2-(phenyl seleno) ethanoicacid (1) and 3-(phenyl seleno) propanoicacid (2) has been synthesized in more economical and efficient method using phase transfer catalyst, tetraethylammonium bromide. Compound 1 & 2, has been synthesised by reacting nucleophile, PhSe- (generated insitu by borohydride reduction of Ph2Se2) with ?-chloro aceticacid & 3-chloro propanoicacid via phase transfer catalysis. The presence of catalyst improves the yield of the products and lowers the reaction time, however in absence of the catalyst yield was very poor. Elemental analysis, IR, 1H, 13C, 1H-1H COSY NMR, ESI mass and molar conductance data has been used to authenticate the new species. The antimicrobial evaluation of both the compounds indicates their significant activity at different concentrations against selected bacterial and fungal strains. These Compound bear an acidic group, showed higher activities due to increase in the lipophilicity and easier penetration of the compounds into the outer cell wall of the microorganisms, which causes death due to cell membrane rupturing thereby boosting the bioactivity of these compounds.

  1. M. Lochowski, K.Kloc, R.Lisiak, P.Potaezek and H.W. Wojtowicz, Arkivoc, VI (2007) 14.
  2. M. Driscoll and P.R. Copeland, Annu. Rev. Nutr., 23 (2003) 17.
  3. Reilly, Selenium in Food and Health, Blackie Academic and Professional, London (1996).
  4. Krief, W.W. Abel, F.G.A. Stone and G.Wilkinson (Eds.), Comprehensive Organometallic Chemistry, Pergamon, Oxford, U.K, (1995) 515.
  5. Carland, T. Fenner, M. Gielen and E.R.T. Tieking (Eds.), Medicine in Metallotherapeutic Drugs and metal Based Diagnostic Agents, Wiley, Chichister, (2005).
  6. Gracia, Curr. Med. Chem., 11 (2004) 1657.
  7. E. Okoronkwo, B. Godoi, R.F. Schumacher, J.S Santos neto, C. Luchese, M. Prigol, C.W. Nogueira and G. Zeni, Tet.Lett., 50 (2009) 909.
  8. B. Singh and N. Sudha, Polyhedron, (1996) 745.
  9. Bochman, Chem. Vapor Depos., 2 (1996) 85.
  10. Mishra, E. Jeanneau and S. Daniele, Polyhedron, 29 (2010) 500.
  11. R. Gray, D.J. Gulliver, W. Levason, M. Webster, J. Chem. Soc., Dalton Trans., (1983) 133.
  12. Mugesh, W.-W. duMont and H. Sies, Chem. Rev., 101 (2001) 2005.
  13. Wu, L.A. Silks, J.D. Odom, R.B. Dunlap, Spectroscopy, 11 (1996) 37.
  14. Kumar, M. Agarwal, A.K. Singh and R.J. Butcher, Inorg. Chim. Acta., 362 (2009) 3208.
  15. Cunha and S.Giorgio, Korean J. Parasitol., 47(3) (2009) 213.
  16. Koketsu, H. Ishihara and M. Hatsu, Res. Commun. Mol. Path. Pharmacol., 179 (1998) 101.
  17. Makosza and M. Fedorynski. Adv. Catal. 35, (1987); E.V. and Dehmlow, S.S. Demlow. Phase-Transfer Catalysis, 3rd ed.;Verlag Chemie, Weinheim 1993.
  18. B. Sharpless and M.W. Young, J. Org. Chem., 40 (1975) 947.
  19. L.F. Armarego and D.D. Perrin, ?Purification of Laboratory Chemicals?, 4th Ed., (1998).
  20. AW Bauer, D M Perry and W M M Kirby, Single disc antibiotic sensitivity testing of Staphylococci. A.M.A, Arch., Intern. Med., ?104 (1959) 208-216.
  21. W. Bauer, W M M Kirby, J C ?Sherris and M Turck, Am. J. Clin. Pathol 36 (1996) 493.
  22. H. Jorgenson and J. D. Turnidge, Manual of Clinical Microbiology 9th Ed. ASM Press, Washington. D.C 1152-1172.
  23. Makoszka, Pure Appl. Chem., 72 (2000) 1399.
  24. J. Geary, Coord. Chem. Rev. Edit. lever, 7 (1971) 110.
  25. M. Silverstein, G. C Bassler and T. C. Morrill, 1998 Spectometric Identification of Organic Compounds (6th Edn) (John Wiley) N.Y.
  26. Khanna, A. Bala and B.L. Khandelwal, J. Organomet. Chem.. 494 (1995) 199.
  27. Akhtar M, K. Sastry and P. Mohan, Mechanism of metal ion biosorption by fungal Biomass, Biometals, 9 (1996) 21?28.

[Richa Saxena and Ambika Chopra. (2018); PHASE TRANSFER CATALYTIC SYNTHESIS, SPECTRAL CHARACTERIZATION AND ANTIMICROBIAL EVALUATION OF 2-(PHENYLSELENO) ETHANOIC ACID AND 3-(PHENYL SELENO) PROPANOIC ACID. Int. J. of Adv. Res. 6 (Apr). 91-96] (ISSN 2320-5407). www.journalijar.com

richa saxena

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Article DOI: 10.21474/IJAR01/6829      
DOI URL: https://dx.doi.org/10.21474/IJAR01/6829

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