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Vol. 26 No. 1 (2014): Vol 26 Issue 1

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Solvent Effects on the Kinetic and Mechanism of N-Mannich Bases of 3-Hydrazonoindole-2-one

https://doi.org/10.14233/ajchem.2014.15316
Tahani Saad Al-Garni
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Amel M. Ismail
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia ; Permanent address: Department of Chemistry, Faculty of Science, Alexandria University, P.O. 426, Ibrahimia, Alexandria 21321, Egypt
Maha Al-Zaben
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia`
Ayman El-Faham
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia`

Corresponding Author(s) : Amel M. Ismail

amelmostafa@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 1 (2014): Vol 26 Issue 1

Abstract

N-Mannich base reaction of 3-hydrazonoindolin-2-one with piperidine in presence of formaldehyde was followed spectrophotometrically in a wide range of water-acetonitrile and water ethanol (10-70 v/v) and at different temperatures (40-60 ºC). The reaction obeys pseudo-first order kinetics. Addition of organic solvent to water decreases the rate of the reaction. A non-linear relation was observed for the plot of log kobs versus the reciprocal of the dielectric constant for the solvent used which suggested that there is a selective solvation by the higher polar solvent, i.e., by water molecules. The thermodynamic parameters DH*, DS* and DG* were calculated and discussed in terms of solvation effects. The determined isokinetic temperatures in both systems, revealed the existence of compensation effect arising from the strong solute-solvent interaction. Finally a suggested mechanism was proposed.

Keywords

Solvent effects Kinetics Mechanism N-Mannich base 3-Hydrazonoindole-2-one
Saad Al-Garni, T., M. Ismail, A., Al-Zaben, M., & El-Faham, A. (2013). Solvent Effects on the Kinetic and Mechanism of N-Mannich Bases of 3-Hydrazonoindole-2-one. Asian Journal of Chemistry, 26(1), 48–52. https://doi.org/10.14233/ajchem.2014.15316
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References
  1. G.J. Kapadia, Y.N. Shukla, S.P. Basak, E.A. Sokoloski and H.M. Fales, Tetrahedron, 36, 2441 (1980); doi:10.1016/0040-4020(80)80221-3.
  2. E.S. Aims, Solvent Effect on Reactions Rates and Mechanisms, Academic Press, London,(1966).
  3. M. Sarangapani and V.M. Reddy, Indian J. Pharm. Sci., 56, 174 (1994).
  4. S.N. Pandeya, D.G. Sriram, G. Nath and E. De Clercq, Pharm. Acta Helv., 74, 11 (1999); doi:10.1016/S0031-6865(99)00010-2.
  5. F.D. Popp, R. Parson and B.E. Donigan, J. Heterocycl. Chem., 17, 1329 (1980); doi:10.1002/jhet.5570170639.
  6. S.N. Pandeya, D. Sriram, G. Nath and E. DeClercq, Eur. J. Pharm. Sci., 9, 25 (1999); doi:10.1016/S0928-0987(99)00038-X.
  7. G.S. Singh, T. Singh and R. Lakhan, Indian J. Chem., 36B, 951 (1997).
  8. S.K. Bhattacharya and S. Chakrabarti, Indian J. Exp. Biol., 36, 118 (1998).
  9. C. Legrand, P. Ropa, B. Vulturescu, A.M. Hogea, G.G. Surpateanu, F. Cazier, P. Woisel and G. Surpateanu, Prog. Org. Coat., 53, 106 (2005); doi:10.1016/j.porgcoat.2004.11.011.
  10. A.M. Ismail, M.S. Ibrahim and H.A. El-Sayed, Alex. J. Pharm.Sci., 8, 3 (1994).
  11. A.M. Ismail and A.A. Zaghloul, Int. J. Chem. Kinet., 30, 463 (1998); doi:10.1002/(SICI)1097-4601(1998)30:7<463::AID-KIN2>3.0.CO;2-Q.
  12. 12.A .M. Ismail, A. H. Ali and H. A. Hanaa, Egypt J. Chem.,45, 105(2002) .
  13. A.M. Ismail, A.H. Ali and H.A. Hanaa, Afindad, 9, 497 (2002).
  14. M.F. Fathalla and A.M. Ismail, Indian J. Chem., 45A, 901 (2006).
  15. R.F. Radman, A.M. Ismail and N.A. Al-Jallal, J. Saudi Chem. Soc., 14, 223 (2010).
  16. A.M. Ismail, Int. J. Chem. Kinet., 44, 125 (2012); doi:10.1002/kin.20624.
  17. A.M. Ismail and S.K. El-Sadany, Prog. Reac. Kint. Mech., 33, 207 (2008); doi:10.3184/146867808X315715.
  18. A M .Ismail, R.F .Radman and N.A. Al-Jallal, Prog. Reac. Kint. Mech., 35, 281 (2010).
  19. R.S. Becker, J. Mol. Spectrosc., 3, 1 (1959); doi:10.1016/0022-2852(59)90002-5.
  20. S. Kunsági-Máté, A. Kumar, P. Sharma, L. Kollár and M.P. Nikfardjam, J. Phys. Chem., B113, 7468 (2009).
  21. N. Karalı, A. Gu¨rsoy, F. Kandemirli, S. Shvets, F.B. Kaynak, S. Özbey, V. Kovalishyn and A. Dimoglo, Bioorgan. Med. Chem., 15, 5888 (2007); doi:10.1016/j.bmc.2007.05.063.
  22. T.A. Emokpae, J. Hirst and P.U. Uwakwe, J. Chem. Soc. Perkin Trans. II, 2191 (1990); doi:10.1039/p29900002191.
  23. J.F. Bunnett and G. Davis, J. Am. Chem. Soc., 82, 665 (1960); doi:10.1021/ja01488a043.
  24. J. Hirst and T.O. Bankole, J. Chem. Soc. B, 848 (1969).
  25. J. Burgess, Metal Ions in Solution, John Wiley & Sons Limited (1978).
  26. Y. Altun, J. Solut. Chem., 33, 479 (2004); doi: 10.1023/B:JOSL.0000037772.55748.a3.
  27. O.C. Kwun, J.B. Kyong and Y.K. Shin, J. Korean Chem. Soc., 30, 40 (1986).
  28. O.C. Kwun and J.R. Kim, J. Korean Chem. Soc., 25, 152 (1981).
  29. M.A. Khalifa, A.M. Ismail and S.M. Soliman, Transition Met. Chem., 32, 163 (2007); doi:10.1007/s11243-006-0141-y.
  30. O.A. El Seoud and F. Siviero, J. Phys. Org. Chem., 19, 793 (2006); doi:10.1002/poc.1081.
  31. G. Akerlof, J. Am. Chem. Soc., 54, 4125 (1932); doi:10.1021/ja01350a001.
  32. L.G. Gagliardi, C.B. Castells, C. Ràfols, M. Rosés and E. Bosch, J. Chem. Eng. Data, 52, 1103 (2007). doi:10.1021/je700055p
  33. K.J. Laidler and P.A. Landskroener, Trans. Faraday Soc., 52, 200 (1956); doi:10.1039/tf9565200200.
  34. C.F. Wells, J. Chem. Soc., Faraday Trans., 73, 1851 (1977); doi:10.1039/f19777301851.
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