TOWARDS A SOLVENT ACIDITY SCALE - THE CALORIMETRY OF THE NORMAL-METHYL IMIDAZOLE PROBE

被引:23
作者
CATALAN, J
COUTO, A
GOMEZ, J
SAIZ, JL
LAYNEZ, J
机构
[1] CSIC,INST QUIM FIS ROCASOLANO,SERRANO 119,E-28006 MADRID,SPAIN
[2] UNIV AUTONOMA MADRID,DEPT QUIM FIS APLICADA,E-28049 MADRID,SPAIN
[3] UNIV NACL EDUC DISTANCIA,DEPT QUIM ORGAN,E-28040 MADRID,SPAIN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1992年 / 07期
关键词
D O I
10.1039/p29920001181
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper reports a rather straightforward calorimetric method for the precise determination of the acidity of organic solvents. From the calculated enthalpies of solvation (DELTA-H(solv)) of the probe compounds N-methylimidazole and N-methylpyrrole and the known relative permittivity (epsilon) of the solvent DELTA-H(acid) is obtained through the equation: DELTA-H(acid) = - [DELTA-H0solv(N-methylimidazole)-DELTA-H0solv(N-methylpyrrole)] + 18.760 f(epsilon) + 1.69. The proposed method allowed us to determine the acidity of 36 solvents, including some slightly acidic ones, whose acidity is difficult to obtain by existing methods.
引用
收藏
页码:1181 / 1185
页数:5
相关论文
共 57 条
[1]   POLARIZABILITY EFFECTS ON THE AQUEOUS-SOLUTION BASICITY OF SUBSTITUTED PYRIDINES [J].
ABBOUD, JLM ;
CATALAN, J ;
ELGUERO, J ;
TAFT, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1137-1140
[2]   STUDIES ON AMPHIPROTIC COMPOUNDS .2. EXPERIMENTAL-DETERMINATION OF THE HYDROGEN-BOND ACCEPTOR BASICITIES OF MONOMERIC ALCOHOLS [J].
ABBOUD, JLM ;
SRAIDI, K ;
GUIHENEUF, G ;
NEGRO, A ;
KAMLET, MJ ;
TAFT, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :2870-2873
[3]   A GENERAL TREATMENT OF HYDROGEN-BOND COMPLEXATION CONSTANTS IN TETRACHLOROMETHANE [J].
ABRAHAM, MH ;
GRELLIER, PL ;
PRIOR, DV ;
TAFT, RW ;
MORRIS, JJ ;
TAYLOR, PJ ;
LAURENCE, C ;
BERTHELOT, M ;
DOHERTY, RM ;
KAMLET, MJ ;
ABBOUD, JLM ;
SRAIDI, K ;
GUIHENEUF, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8534-8536
[4]   HYDROGEN-BONDING .9. SOLUTE PROTON DONOR AND PROTON ACCEPTOR SCALES FOR USE IN DRUG DESIGN [J].
ABRAHAM, MH ;
DUCE, PP ;
PRIOR, DV ;
BARRATT, DG ;
MORRIS, JJ ;
TAYLOR, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (10) :1355-1375
[5]   HYDROGEN-BONDING .7. A SCALE OF SOLUTE HYDROGEN-BOND ACIDITY BASED ON LOG K-VALUES FOR COMPLEXATION IN TETRACHLOROMETHANE [J].
ABRAHAM, MH ;
GRELLIER, PL ;
PRIOR, DV ;
DUCE, PP ;
MORRIS, JJ ;
TAYLOR, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (06) :699-711
[6]   HYDROGEN-BONDING .2. EQUILIBRIUM-CONSTANTS AND ENTHALPIES OF COMPLEXATION FOR 72 MONOMERIC HYDROGEN-BOND ACIDS WITH N-METHYLPYRROLIDINONE IN 1,1,1-TRICHLOROETHANE [J].
ABRAHAM, MH ;
DUCE, PP ;
MORRIS, JJ ;
TAYLOR, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1987, 83 :2867-2881
[7]   STUDIES OF HYDROGEN-BONDED COMPLEX FORMATION .3. THERMODYNAMICS OF COMPLEXING BY INFRARED SPECTROSCOPY AND CALORIMETRY [J].
ARNETT, EM ;
JORIS, L ;
MITCHELL, E ;
MURTY, TSSR ;
GORRIE, TM ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2365-+
[8]   BASICITY - COMPARISON OF HYDROGEN-BONDING AND PROTON-TRANSFER TO SOME LEWIS-BASES [J].
ARNETT, EM ;
MITCHELL, EJ ;
MURTY, TSSR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (12) :3875-3891
[9]   HYDROGEN BONDING .I. 2 APPROACHES TO ACCURATE HEATS OF FORMATION [J].
ARNETT, EM ;
MURTY, TSS ;
SCHLEYER, PV ;
JORIS, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (23) :5955-&
[10]  
BANGO A, 1988, J AM CHEM SOC, V110, P4577