Hydrogen peroxide: A poor ligand to gallium tetraphenylporphyrin

被引：51

作者：

DiPasquale, Antonio G. ^{[1
]}

Mayer, James M. ^{[1
]}

机构：

[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 06期

关键词：

D O I：

10.1021/ja077598w

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

As models for possible heme-iron-H2O2 enzymatic intermediates, tetraphenylporphyrin (TPP)- gallium chemistry has been explored in CD2Cl2. (TPP)GaOTf(1) and (TPP)Ga(ClO4) (2) have been prepared from (TPP)GaCl and AgOTf or AgClO4. Trace water reacts with 2 to give [(TPP) Ga(OH2)](ClO4) (5) and with (TPP)GaOOfBu to give (TPP)GaOH (3). These complexes were fully characterized including X-ray structures for 1, 3, the bis(aquo) analogue of 5, and the methyl derivative (TPP)GaMe (4). A convenient procedure for preparing anhydrous dilute solutions of H2O2 in methylene chloride is described. All of these gallium complexes, however, are unreactive with this anhydrous H2O2 in CD2Cl2. H2O2 does not displace even the weakly coordinating perchlorate or triflate anions, or coordinated water, indicating that H2O2 is a very weak

引用

页码：1812 / +

页数：3

共 36 条

[1]

DETECTION OF ALKYLPEROXO AND FERRYL, (FEIV=O)2+, INTERMEDIATES DURING THE REACTION OF TERT-BUTYL HYDROPEROXIDE WITH IRON PORPHYRINS IN TOLUENE SOLUTION [J].

ARASASINGHAM, RD ;

CORNMAN, CR ;

BALCH, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :7800-7805

[2]

AXIAL ALKYL LIGAND REACTIVITY IN 5-COORDINATE GALLIUM(III) PORPHYRIN COMPLEXES [J].

BALCH, AL ;

HART, RL ;

PARKIN, S .

INORGANICA CHIMICA ACTA, 1993, 205 (02) :137-143

[3]

Hydroxylation by the hydroperoxy-iron species in cytochrome P450 enzymes [J].

Chandrasena, REP ;

Vatsis, KP ;

Coon, MJ ;

Hollenberg, PF ;

Newcomb, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) :115-126

[4]

Cytochrome P450: Nature's most versatile biological catalyst [J].

Coon, MJ .

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 2005, 45 :1-25

[5]

A superoxo-ferrous state in a reduced oxy-ferrous hemoprotein and model compounds [J].

Davydov, R ;

Satterlee, JD ;

Fujii, H ;

Sauer-Masarwa, A ;

Busch, DH ;

Hoffman, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16340-16346

[6]

Substrate modulation of the properties and reactivity of the oxy-ferrous and hydroperoxo-ferric intermediates of cytochrome P450cam as shown by cryoreduction-EPR/ENDOR spectroscopy [J].

Davydov, R ;

Perera, R ;

Jin, SX ;

Yang, TC ;

Bryson, TA ;

Sono, M ;

Dawson, JH ;

Hoffman, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) :1403-1413

[7]

Basis set superposition error-counterpoise corrected potential energy surfaces.: Application to hydrogen peroxide•••X (X=F-, Cl-, Br-, Li+, Na+) complexes [J].

Daza, MC ;

Dobado, JA ;

Molina, JM ;

Salvador, P ;

Duran, M ;

Villaveces, JL .

JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (24) :11806-11813

[8]

Structure and chemistry of cytochrome P450 [J].

Denisov, IG ;

Makris, TM ;

Sligar, SG ;

Schlichting, I .

CHEMICAL REVIEWS, 2005, 105 (06) :2253-2277

[9]

Gauging the relative oxidative powers of compound I, ferric-hydroperoxide, and the ferric-hydrogen peroxide species of cytochrome P450 toward C-H hydroxylation of a radical clock substrate [J].

Derat, E ;

Kumar, D ;

Hirao, H ;

Shaik, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :473-484

[10]

DIPASQUALE AG, THESIS U WASHINGTON

← 1 2 3 4 →