p-Nitrophenolate: A Probe for Determining Acid Strength in Ionic Liquids

被引:31
作者
D'Anna, Francesca [1 ]
La Marca, Sandra [1 ]
Noto, Renato [1 ]
机构
[1] Univ Palermo, Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy
关键词
CARBOXYLIC-ACIDS; AROMATIC-COMPOUNDS; BASE EQUILIBRIA; BINARY-MIXTURES; NONPOLAR MEDIA; BRONSTED ACIDS; PK(A) VALUES; SCALE; SUBSTITUTION; SOLVATION;
D O I
10.1021/jo802473p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In order to obtain an acidity scale in room-temperature ionic liquid solutions, the protonation equilibrium of sodium p-nitrophenolate in [bm(2)im][NTf2] and in [bmpyrr][NTf2], at 298 K, has been studied by means of spectrophotometric titration. Carboxylic acids differing in both structure and in water solution strength have been used. Data collected indicate that in the analyzed ionic liquid solutions carboxylic acids are less dissociated than in water solution. Furthermore, by virtue of a mutual interaction, the studied equilibrium seems to be affected by both the nature of the ionic liquids and the carboxylic acids.
引用
收藏
页码:1952 / 1956
页数:5
相关论文
共 61 条
[51]  
ROGERS RD, 2003, ACS S SERIES, V856
[52]   Acid-base equilibria in nonpolar media. 3. Expanding the spectrophotometric acidity scale in heptane [J].
Room, EI ;
Kaljurand, I ;
Leito, I ;
Rodima, T ;
Koppel, IA ;
Vlasov, VM .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7795-7799
[53]  
STEED WJ, 2000, SUPRAMOL CHEM, P26
[54]   Determination of an acidic scale in room temperature ionic liquids [J].
Thornazeau, C ;
Olivier-Bourbigou, H ;
Magna, L ;
Luts, S ;
Gilbert, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5264-5265
[55]  
Wasserscheid P, 2000, ANGEW CHEM INT EDIT, V39, P3772, DOI 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO
[56]  
2-5
[57]  
Wasserscheid P., 2007, Ionic Liquids in Synthesis, V1
[58]   Room-temperature ionic liquids. Solvents for synthesis and catalysis [J].
Welton, T .
CHEMICAL REVIEWS, 1999, 99 (08) :2071-2083
[59]   The importance of solvent reorganisation in the effect of an ionic liquid on a unimolecular substitution process [J].
Yau, Hon Man ;
Barnes, Susan A. ;
Hook, James M. ;
Youngs, Tristan G. A. ;
Croft, Anna K. ;
Harper, Jason B. .
CHEMICAL COMMUNICATIONS, 2008, (30) :3576-3578
[60]   Efficient esterification of carboxylic acids and phosphonic acids with trialkyl orthoacetate in ionic liquid [J].
Yoshino, T ;
Imori, S ;
Togo, H .
TETRAHEDRON, 2006, 62 (06) :1309-1317