Carboxyester Hydrolysis Promoted by New Zinc(Ⅱ) Macrocyclic Tetraamine Complexes with a Phenol Pendant

Abstract

Abstract: Three new macrocyclic tetraamine ligands(L₁,L₂,L₃) bearing substituted phenolpendant were synthesized and charaterized by elementary analysis, IR, and ¹H NMR.By pHtitration at 25±0.1℃, I=0.1 mol/L KNO₃, studies of protonation of L₃ and complexationof Zn(Ⅱ) with L3 have been carried out and revealed that the pendant phenol deprotonateswith relative low PK_a values of 8.3 and 8.5 for these two cases, respectively.It is due to theformation of hydrogen bond between phenol and proton combining on the nitrogen atoms ofmacrocycle, and the coordination between phenol and Zn(Ⅱ) metal ion.The Zn(Ⅱ)-boundphenol is shown to be a reactive nucleophile and catalyzes 4-nitrophenyl acetate(NA) hydrol-ysis.Akinetic study of NAhydrolysis by these three ligands'Zn (Ⅱ) complexes in 10%(volume ratio) CH₃CNat 25℃, I =0.1 mol/L NaClO₄, and pH 8.63 (20mmol/L Trisbuffer), has established a second-order rate constant k_c/L (mol/L)^-1· s^-1 ]of 3.48×10^-2,1.52×10^-2, 2.85×10^-2, respectively.

Key words: Functionalized macrocycle, Hydrolytic enzyme, Catalysis, Rate constant

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LIN Hua-Kuan, KOU Fu-Ping, ZHU Shou-Rong, CHEN Rong-Ti. Carboxyester Hydrolysis Promoted by New Zinc(Ⅱ) Macrocyclic Tetraamine Complexes with a Phenol Pendant[J]. Chem. J. Chinese Universities, 1997, 18(4): 513.

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Carboxyester Hydrolysis Promoted by New Zinc(Ⅱ) Macrocyclic Tetraamine Complexes with a Phenol Pendant

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