The radical rate-determining step in the oxidation of benzyl alcohols by two N-OH-type mediators of laccase:: the polar N-oxyl radical intermediate

被引：45

作者：

d'Acunzo, F

Baiocco, P

Fabbrini, M

Galli, C ^{[1
]}

Gentili, P

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

[2] Univ Roma La Sapienza, Ctr CNR Meccanismi Reaz, I-00185 Rome, Italy

来源：

NEW JOURNAL OF CHEMISTRY | 2002年 / 26卷 / 12期

关键词：

D O I：

10.1039/b206928h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Determination of the effect of substituents in the aerobic oxidation of X-substituted benzyl alcohols by laccase, with mediation by HPI or HBT, confirms the H-atom abstraction from the benzylic C H bond as the rate-determining step ( HAT route), and supports a polar nature for the N-oxyl radical intermediate originating from the two N-OH mediators.

引用

页码：1791 / 1794

页数：4

共 36 条

[1]

Baciocchi E, 1998, EUR J ORG CHEM, V1998, P299, DOI 10.1002/(SICI)1099-0690(199802)1998:2<299::AID-EJOC299>3.0.CO

[2]

2-B

[3] Spectral properties and absolute rate constants for ß-scission of ring-substituted cumyloxyl radicals.: A laser flash photolysis study [J].

Baciocchi, E ;

Bietti, M ;

Salamone, M ;

Steenken, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2266-2270

[4] Mechanistic aspects of β-bond-cleavage reactions of aromatic radical cations [J].

Baciocchi, E ;

Bietti, M ;

Lanzalunga, O .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (04) :243-251

[5] SIDE-CHAIN OXIDATION OF BENZYLTRIMETHYLSILANES BY IODOSYLBENZENE IN THE PRESENCE OF IRON AND MANGANESE PORPHYRINS [J].

BACIOCCHI, E ;

LANZALUNGA, O .

TETRAHEDRON, 1993, 49 (33) :7267-7276

[6] CARBON SILICON BOND-CLEAVAGE IN THE OXIDATION OF BENZYLIC SILANES BY CERIUM(IV) AMMONIUM-NITRATE [J].

BACIOCCHI, E ;

DEL GIACCO, T ;

ROL, C ;

SEBASTIANI, GV .

TETRAHEDRON LETTERS, 1989, 30 (27) :3573-3576

[7] Reactivities of various mediators and laccases with kraft pulp and lignin model compounds [J].

Bourbonnais, R ;

Paice, MG ;

Freiermuth, B ;

Bodie, E ;

Borneman, S .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1997, 63 (12) :4627-4632

[8] Electrochemical analysis of the interactions of laccase mediators with lignin model compounds [J].

Bourbonnais, R ;

Leech, D ;

Paice, MG .

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 1998, 1379 (03) :381-390

[9]

CANTARELLA G, IN PRESS BIOTECHNOL

[10] The early oxidative biodegradation steps of residual kraft lignin models with laccase [J].

Crestini, C ;

Argyropoulos, DS .

BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (11) :2161-2169

← 1 2 3 4 →