Hydrolysis of Electron-Accepting Esters Catalyzed by Electron--Donating Azoles “Nonclassical” Michaelis Menten Mechanism
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- TAKEISHI Makoto
- Department of Materials Science and Engineering, Faculty of Engineering,
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- YAHAGI Kazuhiro
- Department of Materials Science and Engineering, Faculty of Engineering,
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- OKUYAMA Kohsaku
- Department of Materials Science and Engineering, Faculty of Engineering,
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- MASUYAMA Yoshiyuki
- Department of Materials Science and Engineering, Faculty of Engineering,
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- SATO Rikiya
- Department of Materials Science and Engineering, Faculty of Engineering,
Bibliographic Information
- Other Title
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- 電子供与性アゾール触媒による電子受容性エステルの加水分解-非古典的Michaelis-Menten機構-
- デンシ キョウヨセイ アゾール ショクバイ ニ ヨル デンシ ジュヨウセイ エ
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Abstract
The hydrolyses of electron-accepting esters catalyzed by electron-donating azoles were investigated.1, 2, 3-Benzotriazole accelerated the hydrolysis of 1-naphthyl 3, 5-dinitrobenzoate in the pH range of 7 to 11, whereas the hydrolysis above pH 12 was retarded by the azole. The retardation was attributed to the formation of a charge-transfer complex between the ester and the anionic deprotonated 1, 2, 3-benzotriazole the nucleophilic attack by hydroxide ion on the ester is inhibited by the formation of the anionic complex. This inhibition is expected to take place over all the pH region above neutrality; therefore, the acceleration by the azole below pH 11 can be ascribed to bimolecular nucleophilic attack of free 1, 2, 3benzotriazolide anions on the free ester molecules that overrides the inhibition. The kinetics is expressed by a hyperbolic function which is similar to that for the Michaelis-Menten mechanism in enzymic reactions; however, this catalytic reaction is explained by the “nonclassical”Michaelis-Menten mechanism proposed by Menger.
Journal
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- NIPPON KAGAKU KAISHI
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NIPPON KAGAKU KAISHI 1992 (11), 1356-1362, 1992-11-10
The Chemical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679365519488
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- NII Article ID
- 10006663551
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- NII Book ID
- AN00186595
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- ISSN
- 21850925
- 03694577
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- NDL BIB ID
- 3797243
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed