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The Effect of hydrophobic‐lipophilic interactions on chemical reactivity. 12. Mechanistic investigations of NaCMA‐catalyzed hydrolysis of esters
Author(s) -
Jiang XiKui,
Li XingYa,
Huang BangZhou
Publication year - 1988
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610010304
Subject(s) - chemistry , hydrolysis , catalysis , kinetics , iodide , reactivity (psychology) , saturation (graph theory) , enzyme kinetics , medicinal chemistry , organic chemistry , inorganic chemistry , active site , medicine , physics , alternative medicine , mathematics , pathology , quantum mechanics , combinatorics
Abstract The dependence of the catalytic efficiencies of sodium carboxymethylamylose (NaCMA) for the hydrolysis of N‐lauryl‐3‐acetoxypyridinium iodide ( 1 ) and p ‐nitrophenyl dodecanoate ( 3 ) on its degree of substitution (D. S. = 0·00, 0·12, 0·18, 0·24, 0·29 and 0·35) and on the pH values of the solutions (pH = 7·32, 7·80, 8·10 and 9·30) have been studied. At fixed D. S. values, the observed hydrolysis rates of 1 and 3 increase with increasing concentrations of NaCMA and follow saturation kinetics. At fixed concentration of NaCMA, the rates increase with decreasing D. S. values until they reach maxima at D. S. = 0·00. Furthermore, at any D. S. value the catalytic efficiency increases with increasing pH values of the solutions. All these results indicate that the hydroxyl groups are actually the principal catalyzing groups.