Electronic contributions to the σp parameter of the Hammett equation

被引：83

作者：

Domingo, LR

Pérez, P

Contreras, R

机构：

[1] Univ Valencia, Inst Ciencia Mol, Dept Quim Organ, Valencia, Spain

[2] Univ Andres Bello, Fac Ecol & Recursos Nat, Dept Ciencias Quim, Santiago, Chile

[3] Univ Chile, Fac Ciencias, Dept Quim, Santiago, Chile

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 15期

关键词：

D O I：

10.1021/jo030072j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A statistical procedure to obtain the intrinsic electronic contributions to the Hammett substituent constant sigma(p) is reported. The method is based on the comparison between the experimental sigma(p) values and the electronic electrophilicity index omega evaluated for a series of 42 functional groups commonly present in organic compounds.

引用

收藏

页码：6060 / 6062

页数：3

相关论文

共 22 条

[11] SUBSTITUENT ELECTRONEGATIVITY PARAMETERS [J].

MARRIOTT, S ;

REYNOLDS, WF ;

TAFT, RW ;

TOPSOM, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :959-965

[12] THEORETICAL-STUDIES OF THE INDUCTIVE EFFECT .4. A THEORETICAL SCALE OF SUBSTITUENT FIELD PARAMETERS [J].

MARRIOTT, S ;

TOPSOM, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :7-10

[13] COMPARISON OF THE ELECTROPHILICITIES OF CATIONIC METAL PI-COMPLEXES AND OF ORDINARY CARBENIUM IONS [J].

MAYR, H ;

MULLER, KH ;

RAU, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (11) :1630-1632

[14] Reference scales for the characterization of cationic electrophiles and neutral nucleophiles [J].

Mayr, H ;

Bug, T ;

Gotta, MF ;

Hering, N ;

Irrgang, B ;

Janker, B ;

Kempf, B ;

Loos, R ;

Ofial, AR ;

Remennikov, G ;

Schimmel, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9500-9512

[15] Electrophilicities of iminium ions [J].

Mayr, H ;

Ofial, AR .

TETRAHEDRON LETTERS, 1997, 38 (20) :3503-3506

[16] CARBENIC REACTIVITY REVISITED [J].

MOSS, RA .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (01) :15-21

[17]

Parr R. G., 1989, Density Functional Theory of Atoms and Molecules

[18] Electrophilicity index [J].

Parr, RG ;

Von Szentpály, L ;

Liu, SB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) :1922-1924

[19] ABSOLUTE HARDNESS - COMPANION PARAMETER TO ABSOLUTE ELECTRONEGATIVITY [J].

PARR, RG ;

PEARSON, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7512-7516

[20] Quantitative characterization of the global electrophilicity pattern of some reagents involved in 1,3-dipolar cycloaddition reactions [J].

Pérez, P ;

Domingo, LR ;

Aurell, AJ ;

Contreras, R .

TETRAHEDRON, 2003, 59 (17) :3117-3125