15Apr 2018

MECHANISTICALLY CATIONIC MICELLAR CATALYSIS ON THE HYDROLYSIS OF MONO 2,5-DI METHOXY PHENYL PHOSPHORAMIDE.

  • Abanish Kumar and Pratap Singh, Department of Chemistry, BSA College, Mathura, UP, India, 281OO4.
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Hydrolysis of mono- 2,5-dimethoxy phenyl phosphoramide (mono-2,5-DMPP) was studied in micellar solutions of cetyltrimethylammonium bromide (CTABr) at pH-9.0. The hydrolysis followed first order kinetics with respect to mono-2,5DMPP concentration. At the concentration of critical micelle concentration (CMC) the rate of hydrolysis increased with increasing CTABr concentration. The binding constant of micelle for mono-2,5-DMPP and the rate constant in micellar pseudo phase were determined from kinetic data using the pseudo phase model.


  1. Behme, M.T.A., Cordes, E.H. 1965. Micelle catalysed reaction between anions and neutral molecules. Journal of American Chemical Society, 87: 266-270.
  2. Brinchi, L., Profio, P.D., Garmani, R., Savelli, G., Tugliani, M., Bunton, C.A. 2000. Hydrolysis of dinitroalkoxy phenyl phosphates in aqueous cationic micelles. Langmuir, 16: 10101-10105.
  3. Bruice, T. C., Katzherndler, J., Felder, L. R. 1968. Protein molecule contains both C-O-P and C-N-P linkage. Journal of American Chemical Society, 90: 1333-1348.
  4. Bunton, C.A. 2011. Micellar rate effects: assumptions and approximations, Journal of Organic chemistry in Argentina, 7: 490-504.
  5. Bunton, C.A. Mhala, M.M., Moarres, J.R.D., Saveli, G. 1984. Micellar effects upon dephosphorylation by peroxy anions. Journal of Organic Chemistry, 49: 426-430.
  6. Bunton, C.A., Fendler, E.J., Hameres, F., Young, K.U. 1967. Micellarcatalysed hydrolysis of nitrophenyl phosphate. Journal of Organic Chemistry, 32: 2800-2811.
  7. Bunton, C.A. 1979. Reaction kinetics in aqueous sufactant solution, Catal. Rev. Sci. Eng., 20: 1-56.
  8. Bunton, C.A., Gan, L.H., Moffat, J.R., Romsted, L.S., Savelli, G., 1981. Reaction in micelles of cetyltrimethylammonium hydroxide, test of the pseudophase model for kinetics. J. Phys. Chem., 85: 4118-4125.
  9. Ingold, C.K., 1953. Structure and mechanism in organic chemistry. Cornell University Press, New York.
  10. Duynstee, E.F., Grunward, E. 1959. Kinetics of micellar catalysis and inhibition on alkaline fading of stable tri-phenyl metyl dye cations. Journal of American Chemical Society, 81: 4540-4542.
  11. Ghosh, K.K., Bal, S., Satnami, M.L., Quagliotto, P. ,Dalfonte, P. R. 2008. Effect of cationic surfactant on the hydrolysis of carboxylate and phosphate esters using hydroxamate ions. Journal of colloid and polymer, 286: 293-303.
  12. Al-Lohedan, H., Bunton, C.A., Romsted, L.S. 9181. Micellar effects upon the reaction of betaine esters with hydroxide ion. J. Phys. Chem., 85: 2123-2129.
  13. Al-Lohedan, H., 1995. Quantitative treatment of micellar effects upon nuceophilic substitution. J. Chem. Soc. Perkin Trans, 2: 1707-1713.
  14. Cuccovia, I.M., Schroter, E.H., Monteiro, P.M., Chaimovich, H., 1978. Effect of hexadecyltrimethylammonium bromide on the thiolysis of p-nitrophenyl acetate. J. Org. Chem. 43: 2248-2252.
  15. Cox, J.R., Ramsay, O.B. 1964. Mechanism of nucleophilic substitution in phosphate esters. Chem. Rev.64: 317-352.
  16. R.Cox and O.B.Ramasay, 1964. Chemical Review, 64343.
  17. Jacks, P., Bruno, P. S., Souza, B.S., Micke, G.A., Costa, A., Fiedler, H.D., Bunton, C.A., Nome, F. 2010. Anion specific binding to <i>n<i>- hexadecylphosphoryl chlorine micelles. Langmuir, 26: 1008-1012.
  18. Kumar, A. 2015. SN2 Mechanism of cationic micelles on the hydrolysis of Bis-p-methoxyphenyl phosphate ester, Pak. J. ind. res. Ser. A. phy. Sci., 58 (3): 117-121.
  19. Kumar, A. 2016. Mechanistically cationic micelle on the hydrolysis of tri-p-methoxy phenyl phosphate ester. Internotional Journal of current research, 8 (3): 27374-27377.
  20. Kumar, A., singh, P. 2011. Reaction mechanism of cationic micellar catalysis upon the hydrolysis of mono-p-methoxy phenyl phosphate ester. Journal of Indian Council of Chemists, 28: 56-59.
  21. Al-Shamary, M.N., Al-Lohedan, H.A., Rafiquee, M.Z.A., Issa, Z.A., 2012. Micellar effects on aromatic nucleophilic substitution by the ANRORC mechanism. Hydrolysis of 2-chloro 3,5-dinitropyridine. J. Phys. Org. Chem., 25: 713-719.
  22. Singh, A.P., Verma, R.C., Ragav, S., Prakash. R. 2013. Micellar effect upon dephosphorylation of mono phosphate ester by peroxy anions. Int. J. Chem. Sci. 11(4): 1799-1807.
  23. Yunes, S., Gillitt, N., Bunton, C. 2005. Examination of the pseudophase model of monomer micelle intercoversion in cetylpyridinium chloride. Journal of colloid and interface science, 28 (2): 482-487.

[Gaurav Kumar Singh. (2018); MECHANISTICALLY CATIONIC MICELLAR CATALYSIS ON THE HYDROLYSIS OF MONO 2,5-DI METHOXY PHENYL PHOSPHORAMIDE. Int. J. of Adv. Res. 6 (Apr). 839-844] (ISSN 2320-5407). www.journalijar.com


Dr. ABANISH KUMAR
DEPARTMENT OF CHEMISTRY, BSA COLLEGE, MATHURA, UP INDIA, 281004.

DOI:


Article DOI: 10.21474/IJAR01/6919      
DOI URL: https://dx.doi.org/10.21474/IJAR01/6919