Mononuclear rearrangement of heterocycles in zwitterionic micelles of amine oxide surfactants

被引：9

作者：

Guernelli, Susanna ^{[2
]}

Fontana, Antonella ^{[1
]}

Noto, Renato ^{[3
]}

Spinelli, Domenico ^{[4
]}

Liveri, Maria Liria Turco ^{[5
]}

机构：

[1] Univ G DAnnunzio, Dipartimento Sci Farmaco, I-66013 Chieti, Italy

[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40126 Bologna, Italy

[3] Dipartimento Sci & Tecnol Mol & Biomol STEMBIO, I-90128 Palermo, Italy

[4] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

[5] Dipartimento Chim S Cannizzaro, I-90128 Palermo, Italy

来源：

JOURNAL OF COLLOID AND INTERFACE SCIENCE | 2012年 / 381卷

关键词：

Zwitterionic micelles; Micellar catalysis; N-tetradecyl-N; N-dimethylamineoxide; Mononuclear rearrangements of heterocycles (MRHs); Z-PHENYLHYDRAZONE; BASE-CATALYSIS; IONIC LIQUIDS; GAS-PHASE; WATER; 3-BENZOYL-5-PHENYL-1,2,4-OXADIAZOLE; (Z)-PHENYLHYDRAZONES; ACID; 5-ALKYL-3-BENZOYL-1,2,4-OXADIAZOLES; 5-AMINO-3-BENZOYL-1,2,4-OXADIAZOLE;

D O I：

10.1016/j.jcis.2012.04.074

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Rate constants for the mononuclear rearrangement (MRH) of Z-phenylhydrazones of some 5-substituted-3-benzoyl-1,2,4-oxadiazoles in water have been measured in the presence of zwitterionic micelles. The use of micellized N-tetradecyl-N,N-dimethylamineoxide (C(14)DMAO) as the reaction medium allowed to solubilize the otherwise water-insoluble oxadiazoles. Micellar rate effects were analyzed by using a simple pseudo-phase model and compared with those obtained in non-ionic micelles (Triton X-100). Evidence that both the rate of the rearrangement reaction and the binding of the substrates to the micelles are mainly governed by substrate hydrophobicity is obtained. The disagreement with the primarily sterically controlled MRH in Triton X-100 micelles highlights large and intriguing differences between the two micellar environments. (C) 2012 Elsevier Inc. All rights reserved.

引用

页码：67 / 72

页数：6

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