Mechanism of the acid-catalyzed hydrolysis of N-acylsulfamates

被引：6
|
作者：
Spillane, William J. [1 ]
Malaubier, Jean-Baptiste [1 ]
机构：
[1] Natl Univ Ireland Univ Coll Galway, Galway, Ireland
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 43期
关键词：
D O I：
10.1016/j.tetlet.2007.08.107
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The kinetics of hydrolysis of a series of N-acylsulfamate esters p-XC6H4OSO2NHCOR as models for more complex, biologically important compounds has been examined. Structure-reactivity, solvent-reactivity, thermodynamic data, etc. support a bimolecular mechanism involving water in the transition state (TS). (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7574 / 7577
页数：4
相关论文
共 50 条
  • [1] Synthesis of N-acylsulfamates
    Akrmi, A
    Beji, M
    Baklouti, A
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (01) : 83 - 88
  • [2] MECHANISM OF ACID-CATALYZED HYDROLYSIS OF N,N'-DIARYLACETAMIDINES
    DEWOLFE, RH
    KEEFE, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (02): : 493 - &
  • [3] KINETICS AND MECHANISM OF ACID-CATALYZED HYDROLYSIS OF N-PHENYLSULFAMIC ACID
    SPILLANE, WJ
    GOGGIN, CB
    REGAN, N
    SCOTT, FL
    [J]. INTERNATIONAL JOURNAL OF SULFUR CHEMISTRY, 1976, 8 (04): : 565 - 572
  • [4] AN INVESTIGATION INTO THE MECHANISM OF ACID-CATALYZED HYDROLYSIS OF N-BENZYLBENZOHYDROXAMIC ACID
    GHOSH, KK
    TANDON, SG
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (04) : 1304 - 1307
  • [5] MECHANISM OF ACID-CATALYZED EPOXYETHER HYDROLYSIS
    SCHALEGE.LL
    PORZIO, MA
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1969, (APR): : O164 - &
  • [6] MECHANISM OF ACID-CATALYZED HYDROLYSIS OF POLYSACCHARIDES
    MOISEEV, YV
    KHALTURINSKII, NA
    ZAIKOV, GE
    [J]. CARBOHYDRATE RESEARCH, 1976, 51 (01) : 39 - 54
  • [7] MECHANISM OF ACID-CATALYZED HYDROLYSIS OF GLUCOSIDES
    MOISEEV, YV
    KHALTURINSKII, NA
    ZAIKOV, GE
    [J]. CARBOHYDRATE RESEARCH, 1976, 51 (01) : 23 - 37
  • [8] KINETICS AND MECHANISM OF ACID-CATALYZED HYDROLYSIS OF N-METHYL-N-PHENYLSULFAMATE
    SPILLANE, WJ
    REGAN, N
    SCOTT, FL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (12): : 1424 - 1428
  • [9] MECHANISM OF THE ACID-CATALYZED HYDROLYSIS OF REISSERT COMPOUNDS
    COBB, RL
    MCEWEN, WE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (19) : 5042 - 5048
  • [10] ON THE MECHANISM OF ACID-CATALYZED HYDROLYSIS OF HYDROXAMIC ACIDS
    DIFURIA, F
    MODENA, G
    SCRIMIN, P
    [J]. NOUVEAU JOURNAL DE CHIMIE-NEW JOURNAL OF CHEMISTRY, 1984, 8 (01): : 45 - 49
12345