Hydrolysis of 8-Quinolyl Phosphate Monoester: Kinetic and Theoretical Studies of the Effect of Lanthanide Ions

被引：11

作者：

Souza, Bruno S. ^{[1
]}

Brandao, Tiago A. S. ^{[1
]}

Orth, Elisa S. ^{[1
]}

Roma, Ana C. ^{[2
]}

Longo, Ricardo L. ^{[2
]}

Bunton, Clifford A. ^{[3
]}

Nome, Faruk ^{[1
]}

机构：

[1] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC, Brazil

[2] Univ Fed Recife, Dept Quim Fundamental, BR-50740540 Pernambuco, Brazil

[3] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 03期

关键词：

MOLECULAR-ORBITAL METHODS; GAUSSIAN-TYPE BASIS; PHOSPHORYL TRANSFER; PROTEIN PHOSPHATASES; COMPLEXES; CATALYSIS; MECHANISM; DINUCLEAR; MODELS; EQUILIBRIA;

D O I：

10.1021/jo801870v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

8-Quinolyl phosphate (8QP) in the presence of the trivalent lanthanide ions (Ln = La, Sm, Eu, Tb, and Er) forms a [Ln center dot 8QP](+) complex where the lanthanide ion catalyzes hydrolysis of 8QP. In reactions with Tb3+ or Er3+, there is evidence of limited intervention by a second lanthanide ion. Rate constants are increased by more than 10(7)-fold, and kinetic data and B3LYP/ECP calculations indicate that the effects are largely driven by leaving group and metaphosphate ion stabilization. The lanthanides favor a single-step D(N)A(N) mechanism with a dissociative transition state, with limited nucleophilic assistance, consistent with the low hydroxide ion dependence and the small kinetic effect of Ln(3+) radii.

引用

页码：1042 / 1053

页数：12

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