Premium
Kinetics of hydrolysis of procaine in aqueous and micellar media
Author(s) -
AlBlewi Fawzia Faleh,
AlLohedan Hamad A.,
Rafiquee M. Z. A.,
Issa Zuheir A.
Publication year - 2013
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20735
Subject(s) - chemistry , micelle , hydrolysis , cationic polymerization , bromide , procaine , sodium dodecyl sulfate , aqueous solution , kinetics , pulmonary surfactant , reaction rate constant , inorganic chemistry , procaine hydrochloride , organic chemistry , biochemistry , medicine , physics , quantum mechanics , anesthesia
The kinetics of alkaline hydrolysis of procaine under the pseudo–first‐order condition ([OH − ] ≫ [procaine]) has been carried out. N , N ‐Diethylaminoethanol and p ‐aminobenzoate anion were obtained as the hydrolysis product. The rate of hydrolysis was found to be linearly dependent upon [NaOH]. The addition of cationic cetyltrimethylammonium bromide (CTAB), dodecyltrimethylammonium bromide (DDTAB) and tetradecyltrimethylammonium bromide, and anionic sodium dodecyl sulfate (SDS) micelles inhibited the rate of hydrolysis. The maximum inhibitive effect on the reaction rate was observed for SDS micelles, whereas among the cationic surfactants, CTAB inhibited most. The variation in the rate of hydrolysis of procaine in the micellar media is attributed to the orientation of a reactive molecule to the surfactant and the binding constant of procaine with micelles. The rate of hydrolysis of procaine is negligible in DDTAB micelles. The observed results in the presence of cationic micelles were treated on the basis of the pseudophase ion exchange model. The results obtained in the presence of anionic micelles were treated by the pseudophase model, and the various kinetic parameters were determined. © 2012 Wiley Periodicals, Inc. Int J Chem Kinet 45: 1–9, 2013