Influence of the ionic liquid on the rate and the mechanism of reaction of p-nitrophenyl acetate with secondary alicyclic amines

被引：17

作者：

Millan, Daniela ^{[1
]}

Rojas, Mabel ^{[1
]}

Pavez, Paulina ^{[1
]}

Isaacs, Mauricio ^{[2
]}

Diaz, Carlos ^{[2
]}

Santos, Jose G. ^{[1
]}

机构：

[1] Pontificia Univ Catolica Chile, Fac Quim, Dept Fisicoquim, Santiago, Chile

[2] Pontificia Univ Catolica Chile, Dept Quim Inorgan, Santiago, Chile

来源：

NEW JOURNAL OF CHEMISTRY | 2013年 / 37卷 / 10期

关键词：

SOLVATOCHROMIC COMPARISON METHOD; SUBSTITUTED PYRIDINES; NONLEAVING GROUP; PAIR FORMATION; TEMPERATURE; PYRIDINOLYSIS; AMINOLYSIS; SOLVENTS; KINETICS; NUCLEOFUGALITY;

D O I：

10.1039/c3nj00781b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of p-nitrophenyl acetate (1) with piperidine was studied in nine organic solvents and in nine ionic liquids. The aminolysis of 1 by four different secondary amines was also studied in [Bmim]BF4 and their basicities were determined in this solvent using two different methods. Medium effects were analysed and interpreted by comparing the rate constants of aminolysis for the two sets of solvents.

引用

页码：3281 / 3288

页数：8

共 53 条

[1] Angelini G, 2010, J ORG CHEM, V75, P3912, DOI [10.1021/jo.100570x, 10.1021/jo100570x]
[2] Examination of ionic liquids and their interaction with molecules, when used as stationary phases in gas chromatography
Armstrong, DW
He, LF
Liu, YS
[J]. ANALYTICAL CHEMISTRY, 1999, 71 (17) : 3873 - 3876
[3] Electrochemical Determination of pKa of N-Bases in Ionic Liquid Media
Barhdadi, Rachid
Troupel, Michel
Comminges, Clement
Laurent, Michel
Doherty, Andrew
[J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2012, 116 (01) : 277 - 282
[4] KINETICS OF REACTION OF SUBSTITUTED PYRIDINES AND OXYGEN ANIONS WITH METHYL CHLOROFORMATE IN AQUEOUS-SOLUTION
BOND, PM
CASTRO, EA
MOODIE, RB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (01): : 68 - 72
[5] Electrofugality index for benzhydryl derivatives
Campodonico, Paola R.
Perez, Claudio
Aliaga, Margarita
Gazitua, Marcela
Contreras, Renato
[J]. CHEMICAL PHYSICS LETTERS, 2007, 447 (4-6) : 375 - 378
[6] Nucleofugality index in α-elimination reactions
Campodonico, Paola R.
Andres, Juan
Aizman, Arie
Contreras, Renato
[J]. CHEMICAL PHYSICS LETTERS, 2007, 439 (1-3) : 177 - 182
[7] Group electrophilicity as a model of nucleofugality in nucleophilic substitution reactions
Campodonico, Paola R.
Aizman, Arie
Contreras, Renato
[J]. CHEMICAL PHYSICS LETTERS, 2006, 422 (4-6) : 340 - 344
[8] Reactivity of benzohydrazide derivatives towards acetylation reaction. Experimental and theoretical studies
Campodonico, Paola R.
Aliaga, Margarita E.
Santos, Jose G.
Castro, Enrique A.
Contreras, Renato
[J]. CHEMICAL PHYSICS LETTERS, 2010, 488 (1-3) : 86 - 89
[9] NONLINEAR BRONSTED-TYPE PLOT IN THE PYRIDINOLYSIS OF 2,4-DINITROPHENYL BENZOATE IN AQUEOUS ETHANOL
CASTRO, EA
SANTANDER, CL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) : 3595 - 3600
[10] Castro EA, 1998, INT J CHEM KINET, V30, P267, DOI 10.1002/(SICI)1097-4601(1998)30:4<267::AID-KIN4>3.0.CO

← 1 2 3 4 5 6 →