A straightforward detection of deprotonated conformers of malonic acid by solid-state 13C NMR spectroscopy

被引:12
作者
Colsenet, R
Gardiennet, C
Henry, B
Tekely, P [1 ]
机构
[1] Univ H Poincare Nancy 1, FRE 2415, CNRS, Lab Methodol RMN, F-54500 Vandoeuvre Les Nancy, France
[2] Univ H Poincare Nancy 1, Lab Chim Phys Organ & Colloidale, UMR 7565, CNRS, F-54500 Vandoeuvre Les Nancy, France
关键词
D O I
10.1002/anie.200290035
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
Information about the presence and the nature of various deprotonated forms of malonic acid in lyophilizates prepared from parent solutions at different pH values can be obtained by solid-state, natural abundance 13C NMR spectroscopy, particularly if a 13C-enriched substrate is used (see picture). pK values calculated from solid-state acid:base ratios are found to be equal to those classically measured in the liquid state.
引用
收藏
页码:4743 / 4745
页数:3
相关论文
共 13 条
[1]
THE EFFECT OF PH ON SOLID-STATE C-13 NMR-SPECTRA OF HISTIDINE [J].
FREY, MH ;
OPELLA, SJ .
JOURNAL OF MAGNETIC RESONANCE, 1986, 66 (01) :144-147
[2]
HYDROGEN-BONDING OF CARBOXYL GROUPS IN SOLID-STATE AMINO-ACIDS AND PEPTIDES - COMPARISON OF CARBON CHEMICAL SHIELDING, INFRARED FREQUENCIES, AND STRUCTURES [J].
GU, ZT ;
ZAMBRANO, R ;
MCDERMOTT, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6368-6372
[3]
CHEMICAL SHIELDING ANISOTROPY OF PROTONATED AND DEPROTONATED CARBOXYLATES IN AMINO-ACIDS [J].
GU, ZT ;
MCDERMOTT, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4282-4285
[4]
pH and pK determinations by high-resolution solid-state 13C NMR:: Acid-base and tautomeric equilibria of lyophilized L-histidine [J].
Henry, B ;
Tekely, P ;
Delpuech, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :2025-2034
[5]
C-13 CHEMICAL SHIELDING TENSORS IN ALKANEDICARBOXYLIC ACIDS - INFLUENCE OF MOLECULAR-GEOMETRY ON THE CARBOXYL CARBON TENSORS IN ALKANEDICARBOXYLIC ACIDS AND RELATED-COMPOUNDS [J].
JAGANNATHAN, NR .
MAGNETIC RESONANCE IN CHEMISTRY, 1989, 27 (10) :941-946
[6]
Conformational analysis and near-infrared-induced rotamerization of malonic acid in an argon matrix [J].
Maçôas, EMS ;
Fausto, R ;
Lundell, J ;
Pettersson, M ;
Khriachtchev, L ;
Räsänen, M .
JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (50) :11725-11732
[7]
MERCHAN M, 1984, J MOL STRUCT THEOCHE, V109, P51
[8]
Mundy JN., 1983, SOLID STATE NUCL MET
[9]
POWELL JF, 1992, IUPAC STABILITY CONS
[10]
MOLECULAR SEQUENCE EFFECT ON THE C-13 CARBONYL CHEMICAL-SHIFT SHIELDING TENSOR [J].
SEPAROVIC, F ;
SMITH, R ;
YANNONI, CS ;
CORNELL, BA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8324-8328