Empirical scale of nucleophilicity for substituted pyridines

被引：25

作者：

Campodónico, PR

Aizman, A

Contreras, R

机构：

[1] Univ Chile, Fac Ciencias, Dept Fis, Santiago, Chile

[2] Univ Tecn Federico Santa Maria, Dept Quim, Valparaiso, Chile

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

来源：

CHEMICAL PHYSICS LETTERS | 2006年 / 422卷 / 1-3期

关键词：

D O I：

10.1016/j.cplett.2006.02.045

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Two classical tools, the intermolecular stretching force constants of H-bonded complexes and the molecular electrostatic potential are used to propose a nucleophilicity index evaluated for a series of pyridines. The model is validated against kinetic data recorded for the aminolysis of S-methyl 2,4-dinitrophenyl thiocarbonate. (c) 2006 Elsevier B.V. All rights reserved.

引用

收藏

页码：204 / 209

页数：6

相关论文

共 32 条

[1] Investigation of the gas phase infrared spectrum of HF complexed with dimethyl ether from both cell- and supersonic jet-FTIR experiments [J].

Asselin, P ;

Soulard, P ;

Alikhani, ME ;

Perchard, JP .

CHEMICAL PHYSICS, 2000, 256 (02) :195-205

[2] ELECTROSTATIC PREDICTIONS OF SHAPES AND PROPERTIES OF VANDERWAALS MOLECULES [J].

BUCKINGHAM, AD ;

FOWLER, PW ;

STONE, AJ .

INTERNATIONAL REVIEWS IN PHYSICAL CHEMISTRY, 1986, 5 (2-3) :107-114

[3] Relationship between nucleophilicity/electrophilicity indices and reaction mechanisms for the nucleophilic substitution reactions of carbonyl compounds [J].

Campodonico, P ;

Santos, JG ;

Andres, J ;

Contreras, R .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2004, 17 (04) :273-281

[4] Relationships between the electrophilicity index and experimental rate coefficients for the aminolysis of thiolearbonates and dithiocarbonates [J].

Campodónico, RR ;

Fuentealba, P ;

Castro, EA ;

Santos, JG ;

Contreras, R .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1754-1760

[5] Kinetics and mechanism of the pyridinolysis of 4-nitrophenyl and 2,4-dinitrophenyl S-methyl thiocarbonates [J].

Castro, EA ;

Aliaga, M ;

Santos, JG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) :6711-6714

[6] A theoretical study on the relationship between nucleophilicity and ionization potentials in solution phase [J].

Contreras, R ;

Andres, J ;

Safont, VS ;

Campodonico, P ;

Santos, JG .

JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (29) :5588-5593

[7] PROPERTIES OF HYDROGEN-BONDED COMPLEXES OBTAINED FROM THE B3LYP FUNCTIONAL WITH 6-31G(D,P) AND 6-31+G(D,P) BASIS-SETS - COMPARISON WITH MP2/6-31+G(D,P) RESULTS AND EXPERIMENTAL-DATA [J].

DELBENE, JE ;

PERSON, WB ;

SZCZEPANIAK, K .

JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (27) :10705-10707

[8] POLARIZABILITY, BASICITY AND NUCLEOPHILIC CHARACTER [J].

EDWARDS, JO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (09) :1819-1820

[9] CORRELATION OF RELATIVE RATES AND EQUILIBRIA WITH A DOUBLE BASICITY SCALE [J].

EDWARDS, JO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (06) :1540-1547

[10]

Frisch M.J., 1998, GAUSSIAN 98

← 1 2 3 4 →