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Kinetic Study of Hydrolysis of Mono-3,5-dimethylaniline Phosphate in Buffer Medium
Corresponding Author(s) : S.A. Bhoite
Asian Journal of Chemistry,
Vol. 29 No. 5 (2017): Vol 29 Issue 5
Abstract
In present investigation, hydrolysis of mono-3,5-dimethylaniline phosphate was studied in buffer medium at 50 °C in pH range 0.00 to 7.68. The rate of hydrolysis was measured by determining the rate of inorganic phosphate by spectrophotometer. Pseudo first order rate coefficients were obtained. The rate of reaction increased with increase in pH up to 4.04. The maximum value at pH 4.04 is due to hydrolysis via mononegative and neutral species. Their dinegative species have been found to be inert. The theoretical rate determined from specific rate and fraction of the neutral species agree closely with the experimental rates. Bond fission and bimolecular nature of hydrolysis have been supported by Arrhenius parameters and study of solvent effect. The hydrolysis of monoester involves P-N bond fission, which is strengthened by comparative kinetic rate data.
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- K.S. Kumar, C.B. Reddy, M.V.N. Reddy, C.R. Rani and C.S. Reddy, Org. Commun., 5, 50 (2012).
- S.J. Hecker and M.D. Erion, J. Med. Chem., 51, 2328 (2008); https://doi.org/10.1021/jm701260b.
- R.A. Moss and H. Morales-Rojas, J. Am. Chem. Soc., 123, 7457 (2001); https://doi.org/10.1021/ja004156a.
- L. Cisse and T. Mrabet, Phosphorus Res. Bull., 15, 21 (2004); https://doi.org/10.3363/prb1992.15.0_21.
- S. Ikeno and T. Haruyama, Sens. Actuators B Chem., 108, 608 (2005); https://doi.org/10.1016/j.snb.2004.11.077.
- H. Yadav, M.K. Gupta and S.A. Bhoite, Int. J. Chem. Technol. Res., 7, 2731 (2015).
- C. Fest and K.J. Schmidt, The Chemistry of Organophosphorus Pesticides, Springer-Verlag, Berlin (1982).
- P.N. Manne, S.D. Deshmukh, N.G.N. Rao, H.G. Dodale, S.N. Tikar and S.A. Nimbalkar, Pestology, 34, 65 (2000).
- D. Hendlin, E.O. Stapley, M. Jackson, H. Wallick, A.K. Miller, F.J. Wolf, T.W. Miller, L. Chaiet, F.M. Kahan, E.L. Foltz, H.B. Woodruff, J.M. Mata, S. Hernandez and S. Mochales, Science, 166, 122 (1969); https://doi.org/10.1126/science.166.3901.122.
- M.S. Bhatia and Pawanjit, Experienia, 32, 1111 (1976); https://doi.org/10.1007/BF01927572.
- A.M. Polozov and S.E. Cremer, J. Organomet. Chem., 646, 153 (2002); https://doi.org/10.1016/S0022-328X(01)01207-4.
- J.G. Zalatan and D. Herschlag, J. Am. Chem. Soc., 128, 1293 (2006); https://doi.org/10.1021/ja056528r.
- A. Alkherraz, S.C.L. Kamerlin, G. Feng, Q.I. Sheikh, A. Warshel and N.H. Williams, Faraday Discuss., 145, 281 (2010); https://doi.org/10.1039/B908398G.
- J. Cavalier, Bull. Soc. Chim. Fr., 189, 885 (1895).
- R.J.L. Allen, Biochem. J., 34, 858 (1940); https://doi.org/10.1042/bj0340858.
- A.A. Frost and R.G. Pearson, Kinetics and Mechanism, John Wiley & Sons, New York, p. 331 (1961).
- J.D. Chanley and E.J. Feageson, J. Am. Chem. Soc., 80, 2686 (1958); https://doi.org/10.1021/ja01544a025.
References
K.S. Kumar, C.B. Reddy, M.V.N. Reddy, C.R. Rani and C.S. Reddy, Org. Commun., 5, 50 (2012).
S.J. Hecker and M.D. Erion, J. Med. Chem., 51, 2328 (2008); https://doi.org/10.1021/jm701260b.
R.A. Moss and H. Morales-Rojas, J. Am. Chem. Soc., 123, 7457 (2001); https://doi.org/10.1021/ja004156a.
L. Cisse and T. Mrabet, Phosphorus Res. Bull., 15, 21 (2004); https://doi.org/10.3363/prb1992.15.0_21.
S. Ikeno and T. Haruyama, Sens. Actuators B Chem., 108, 608 (2005); https://doi.org/10.1016/j.snb.2004.11.077.
H. Yadav, M.K. Gupta and S.A. Bhoite, Int. J. Chem. Technol. Res., 7, 2731 (2015).
C. Fest and K.J. Schmidt, The Chemistry of Organophosphorus Pesticides, Springer-Verlag, Berlin (1982).
P.N. Manne, S.D. Deshmukh, N.G.N. Rao, H.G. Dodale, S.N. Tikar and S.A. Nimbalkar, Pestology, 34, 65 (2000).
D. Hendlin, E.O. Stapley, M. Jackson, H. Wallick, A.K. Miller, F.J. Wolf, T.W. Miller, L. Chaiet, F.M. Kahan, E.L. Foltz, H.B. Woodruff, J.M. Mata, S. Hernandez and S. Mochales, Science, 166, 122 (1969); https://doi.org/10.1126/science.166.3901.122.
M.S. Bhatia and Pawanjit, Experienia, 32, 1111 (1976); https://doi.org/10.1007/BF01927572.
A.M. Polozov and S.E. Cremer, J. Organomet. Chem., 646, 153 (2002); https://doi.org/10.1016/S0022-328X(01)01207-4.
J.G. Zalatan and D. Herschlag, J. Am. Chem. Soc., 128, 1293 (2006); https://doi.org/10.1021/ja056528r.
A. Alkherraz, S.C.L. Kamerlin, G. Feng, Q.I. Sheikh, A. Warshel and N.H. Williams, Faraday Discuss., 145, 281 (2010); https://doi.org/10.1039/B908398G.
J. Cavalier, Bull. Soc. Chim. Fr., 189, 885 (1895).
R.J.L. Allen, Biochem. J., 34, 858 (1940); https://doi.org/10.1042/bj0340858.
A.A. Frost and R.G. Pearson, Kinetics and Mechanism, John Wiley & Sons, New York, p. 331 (1961).
J.D. Chanley and E.J. Feageson, J. Am. Chem. Soc., 80, 2686 (1958); https://doi.org/10.1021/ja01544a025.