INTRAMOLECULAR PARTICIPATION OF THE AMIDE GROUP IN ACID-CATALYZED AND BASE-CATALYZED PHOSPHONATE MONOESTER HYDROLYSIS

被引：26

作者：

RAHIL, J ^{[1
]}

PRATT, RF ^{[1
]}

机构：

[1] WESLEYAN UNIV, DEPT CHEM, MIDDLETOWN, CT 06457 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1991年 / 07期

关键词：

D O I：

10.1039/p29910000947

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rates of hydrolysis of monoaryl alpha-amidophosphonates in both acid and alkaline solutions are much greater than those of comparable compounds lacking the amido substituent; intramolecular nucleophilic catalysis seems likely. This phenomenon may be important in the employment of alpha-amidophosphonate derivatives as enzyme inhibitors.

引用

收藏

页码：947 / 950

页数：4

相关论文

共 36 条

[1]

[Anonymous], 1976, HDB BIOCH MOL BIOL P

[2] PHOSPHONAMIDATES AS TRANSITION-STATE ANALOG INHIBITORS OF THERMOLYSIN [J].

BARTLETT, PA ;

MARLOWE, CK .

BIOCHEMISTRY, 1983, 22 (20) :4618-4624

[3] EFFECTIVE CHARGE-DISTRIBUTION FOR ATTACK OF PHENOXIDE ION ON ARYL METHYL PHOSPHATE MONOANION - STUDIES RELATED TO THE ACTION OF RIBONUCLEASE [J].

BASAIF, SA ;

DAVIS, AM ;

WILLIAMS, A .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) :5483-5486

[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]

BOWDEN K, 1990, J CHEM RES-S, P344

[6] REACTIONS OF CARBONYL COMPOUNDS IN BASIC SOLUTIONS .2. MECHANISM OF ALKALINE HYDROLYSIS OF METHYL 2-BENZOYLBENZOATES [J].

BOWDEN, K ;

TAYLOR, GR .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (01) :145-&

[7] REACTIONS OF CARBONYL COMPOUNDS IN BASIC SOLUTIONS .3. MECHANISM OF ALKALINE HYDROLYSIS OF METHYL 2-AROYL-BENZOATES AND 2-ACYL-BENZOATES AND RELATED ESTERS [J].

BOWDEN, K ;

TAYLOR, GR .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (01) :149-&

[8]

BOWDEN K, 1990, J CHEM RES M, P2682

[9]

BRUICE TC, 1966, BIOORG MECH, V1, P166

[10] BASE-CATALYSED INTRAMOLECULAR NUCLEOPHILIC KETO-GROUP PARTICIPATION IN SOLVOLYSIS OF HINDERED ESTER, 2-ACETYLPHENYL MESITOATE - ACETAL FORMATION UNDER BASIC CONDITIONS AS A MECHANISTIC CONSEQUENCE OF SUCH PARTICIPATION [J].

BURROWS, HD ;

TOPPING, RM .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (07) :1323-&

← 1 2 3 4 →