Metal cation micelle mediated hydrolysis of phosphonic acid esters

被引：35

作者：

Moss, RA ^{[1
]}

Ragunathan, KG ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem, New Brunswick, NJ 08903 USA

来源：

LANGMUIR | 1999年 / 15卷 / 01期

关键词：

D O I：

10.1021/la981110a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

p-Nitrophenyl methylphosphonate (PNPMP, 3) and p-nitrophenyl phenylphosphonate (PNPPP, 4) are rapidly hydrolyzed in acidic solutions (pH 3.5-6.0) at 37 degrees C by excess Zr4+, Ce4+, or Th4+ cations. Brij-35 micelles are employed in the Ce4+ and Th4+ cases. Second-order rate constants (M-1 s(-1)) with PNPMP are 115 (Zr4+), 53.9 (Ce4+), and 16.9 (Th4+), while for PNPPP they are, respectively, 76.8, 16.1, and 13.1. Relative to water (k(2) = 3.6 x 10(-11) M-1 s(-1) at 30 degrees C, pH 7.6), kinetic advantages with Zr4+ or. Ce4+ exceed 10(12).

引用

页码：107 / 110

页数：4

共 39 条

[1]

ARNAUDNEU F, 1994, CHEM SOC REV, P235

[2] REACTIONS OF ORGANIC PHOSPHATES .6. HYDROLYSIS OF ARYL PHOSPHATES [J].

BARNARD, PWC ;

BUNTON, CA ;

KELLERMA.D ;

MHALA, MM ;

SILVER, B ;

VERNON, CA ;

WELCH, VA .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (03) :227-&

[3] REACTIONS OF PHOSPHONIC ACID ESTERS WITH NUCLEOPHILES .1. HYDROLYSIS [J].

BEHRMAN, EJ ;

BIALLAS, MJ ;

BRASS, HJ ;

EDWARDS, JO ;

ISAKS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (09) :3063-&

[4] REACTIONS OF PHOSPHONIC ACID ESTERS WITH NUCLEOPHILES .2. SURVEY OF NUCLEOPHILES REACTING WITH PARA-NITROPHENYL METHYLPHOSPHONATE ANION [J].

BEHRMAN, EJ ;

BIALLAS, MJ ;

BRASS, HJ ;

EDWARDS, JO ;

ISAKS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (09) :3069-&

[5] YTTRIUM(III) CATALYSED HYDROLYSIS OF ACID PHOSPHONATE ESTERS [J].

BLEWETT, FM ;

WATTS, P .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (05) :881-&

[6] Remarkably rapid cleavage of a model phosphodiester by complexed ceric ions in aqueous micellar solutions [J].

Bracken, K ;

Moss, RA ;

Ragunathan, KG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) :9323-9324

[7] CLEAVAGE OF PHOSPHATE-ESTERS BY A CYCLODEXTRIN DIMER CATALYST THAT BINDS THE SUBSTRATES TOGETHER WITH LA3+ AND HYDROGEN-PEROXIDE [J].

BRESLOW, R ;

ZHANG, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7893-7894

[8] EFFECTS OF METAL-IONS, INCLUDING MG2+ AND LANTHANIDES, ON THE CLEAVAGE OF RIBONUCLEOTIDES AND RNA MODEL COMPOUNDS [J].

BRESLOW, R ;

HUANG, DL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (10) :4080-4083

[9] HYDROLYSIS OF BIS(2,4-DINITROPHENYL) PHOSPHATE [J].

BUNTON, CA ;

FARBER, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) :767-&

[10]

BURGESS J, 1978, METAL IONS SOLUTION, P265

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