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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 3, Number 1
January 20, 1982 

Hydrophobic and Ionic Interactions in the Ester Hydrolysis by Imidazole-Containing Polymers
Iwhan Cho, Jae-Sup Shin
N-Methacryloyl-L-histidine and N-methacryloyl-L-histidine methyl ester were synthesized and polymerized to obtain polymeric catalysts with different functions. In the presence of each of these polymers the solvolytic reactions of p-nitrophenyl acetate (PNPA), 3-nitro-4-acetoxybenzoic acid(NABA), 3-acetoxy-N-trimethylanilinium iodide(ANTI) and 3-nitro-4-decanoyloxybenzoic acid(NDBA) were performed in 20% aqueous ethanol. For the purpose of comparison the low molecular weight analogs(LMWA's), L-histidine, L-histidine methyl ester and N-acetyl-L-histidine were also subjected to catalyze the solvolyses of above substrates. In the solvolysis of PNPA the polymeric catalysts exhibited lower activities than the LMWA's. However the ionic substrates, NABA and ANTI were solvolyzed at anomalous rate by polymeric catalyst, indicating that electrostatic effects are operative in the catalysis by polymers. Furthermore in the solvolysis of hydrophobic monomer NDBA, polymeric catalysts exhibited highly enhanced activities compared with the LMWA's implying that hydrophobic interaction can be the most important contribution to the high catalytic activity of imidazole-containing polymers.
34 - 36
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