Abstract
Kinetics of the hydrolysis of isoproturon by hydrochloric acid has been studied spectrophotometrically in the absence and the presence of anionic sodium lauryl sulfate (NaLS) micelles. The anionic micelle was found to increase the rate of reaction. The reaction followed first-order kinetics with respect to isoproturon and was linearly dependent upon [HCl]. In both aqueous and micellar pseudophases, the reaction was started with the protonation of the amino group of isoproturon followed by attack of water to yield phenylcarbamic acid and the corresponding amine, thus obeying the addition–elimination mechanism. The surfactant decreased the activation entropy. The binding constant in consistence with the rate constants was evaluated on the basis of pseudophase ion-exchange model. The added salts (NaCl and KCl) decreased the rate of reaction due to the exclusion of H+ from micellar surfaces.
References
Fendler JH (1982) Membrane mimetic chemistry. Wiley, New York
Rosen MJ (1978) Surfactants and interfacial phenomena. Wiley, New York
Shah DO (ed) (1985) Micro- and macroemulsions: theory and practice. ACS Symposium Series 272, American Chemical Society, Washington, DC
Cutler WG, Kissa E (1987) Detergency: theory and technology. Marcel Dekker, New York
El-Nokaly M, Cornell D (eds) (1991) Microemulsions and emulsions in food. ACS Symposium Series 448, American Chemical Society, Washington, DC
Tonellato U (1988) J Chim Phys Phys-Chim Biol 85:1047
Tanford C (1980) The hydrophobic effect: formation of micelles and biological membranes, 2nd edn. Wiley, New York
Jain MK (1988) Introduction to biological membranes, 2nd edn. Wiley, New York, p 423
Bunton CA (1991) In: Gratzel M, Kalyanasundaram K (eds) Kinetics and catalysis in microheterogeneous systems. Marcel Dekker, New York, p 525
Bunton CA, Nome F, Quina FH, Romsted LS (1991) Acc Chem Res 24:357
Bunton CA, Savelli G (1986) Adv Phys Org Chem 22:213
Salvestrini S, Di Cerbo P, Capasso S (2002) J Chem Soc Perkin Trans 2:1893
Laudien R, Mitzner R (2001) J Chem Soc Perkin Trans 2:2230–2232
O’Connor CJ, Barnett JW (1973) J Chem Soc Perkin Trans 2:1457–1461
Giffney JC, O’Connor CJ (1976) J Chem Soc Perkin Trans 2:362–368
Vera S, Rodenas E (1986) Tetrahedron 42:143–149
Shinoda K, Lindman B (1987) Langmuir 3:135
Ruzza AA, Nome F, Zanette D (1995) Langmuir 11:2393
Connors KA (1990) Chemical kinetics: the study of reaction rate in solutes. VCH, New York, USA
Spindli D, Noto R, Consiglo G, Werber G, Buchheri F (1978) J Org Chem 43:4042
Broxton TR, Deady LW, Duddy NW (1978) Aust J Chem 31:1525
Gensmental NG, Page MI (1982) J Chem Soc Perkin Trans 147
Bunton CA, Robinson L (1969) J Org Chem 34:773
Anacker EW, Ghose HM (1968) J Am Chem Soc 90:3161
Bunton CA, Wolfe B (1973) J Am Chem Soc 95:3742
Acknowledgment
The authors are thankful to the chairman, Department of Applied Chemistry, Z.H. College of Engineering & Technology, Aligarh Muslim University, and Aligarh for providing research facilities.
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Gangwar, S.K., Rafiquee, M.Z.A. Kinetics of the acid hydrolysis of isoproturon in the absence and presence of sodium lauryl sulfate micelles. Colloid Polym Sci 285, 587–592 (2007). https://doi.org/10.1007/s00396-006-1596-2
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DOI: https://doi.org/10.1007/s00396-006-1596-2