Hydrogen bonds in carboxylic acid-carboxylate systems in solution.: 1.: In anhydrous, aprotic media

被引:27
作者
Brück, A [1 ]
McCoy, LL [1 ]
Kilway, KV [1 ]
机构
[1] Univ Missouri, Dept Chem, Kansas City, MO 64110 USA
关键词
D O I
10.1021/ol005776j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS Preliminary NMR studies on hydrogen bonding of carboxylic acid-carboxylate systems in an anhydrous, aprotic solvent are presented. In all cases, a tow-field resonance (16-20 ppm) indicative of strong hydrogen bonding was observed. From these results, it seems probable that this characteristic downfield shift should be exhibited by all carboxylic acid-carboxylate systems in anhydrous, aprotic media.
引用
收藏
页码:2007 / 2009
页数:3
相关论文
共 14 条
[1]   Low-barrier hydrogen bonding in aqueous and aprotic solutions of dicarboxylic acids: Spectroscopic characterization [J].
Cassidy, CS ;
Lin, J ;
Tobin, JB ;
Frey, PA .
BIOORGANIC CHEMISTRY, 1998, 26 (04) :213-219
[2]   VERY STRONG HYDROGEN-BONDS FORMED BETWEEN CARBOXYLIC-ACIDS AND ANIONS - TRIFLUOROACETIC AND ACETIC-ACIDS WITH ACETATES AND FLUORIDE [J].
CLARK, JH ;
EMSLEY, J .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (11) :1125-1129
[3]   INTRAMOLECULAR HYDROGEN BONDING AS A FACTOR IN DETERMINING K1-K2 RATIOS OF DICARBOXYLIC ACIDS [J].
EBERSON, L ;
WADSO, I .
ACTA CHEMICA SCANDINAVICA, 1963, 17 (06) :1552-&
[4]  
Hibbert F., 1990, ADV PHYS ORG CHEM, V26, P255, DOI DOI 10.1016/S0065-3160(08)60047-7
[5]   PROTON MAGNETIC-RESONANCE SPECTRA IN TRIFLUOROACETIC ACID SOLUTION .1. ALKALI-METAL AND QUATERNARY AMMONIUM TRIFLUOROACETATES [J].
JONES, RG ;
DYER, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (08) :2465-2470
[6]   ACID DISSOCIATION CONSTANTS OF SOME 1,2-CYCLOPROPANEDICARBOXYLIC ACIDS - SOME COMMENTS CONCERNING ACID DISSOCIATION CONSTANTS OF DICARBOXYLIC ACIDS [J].
MCCOY, LL ;
NACHTIGA.GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (09) :1321-&
[8]   Characterization of low-barrier hydrogen bonds. 6. Cavity polarity effects on the formic acid formate anion model system. An ab initio and DFT investigation [J].
Pan, YP ;
McAllister, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) :166-169
[9]   Symmetry of hydrogen bonds in solution, an overview [J].
Perrin, CL ;
Nielson, JB ;
Kim, YJ .
BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1998, 102 (03) :403-409
[10]   Asymmetry of hydrogen bonds in solutions of monoanions of dicarboxylic acids [J].
Perrin, CL ;
Nielson, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (52) :12734-12741