Prototropic equilibrium in complexes of N-methylmorpholine betaine with phenols studied by NMR and UV spectroscopy

被引：22

作者：

Dega-Szafran, Z ^{[1
]}

Sokolowska, E ^{[1
]}

机构：

[1] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2001年 / 565卷

关键词：

N-methylmorpholine betaine; phenols; prototropic equilibrium; NMR spectroscopy; UV spectroscopy;

D O I：

10.1016/S0022-2860(00)00954-6

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Fourteen complexes of N-methylmorpholine betaine (MMBet) with phenols (pK(a) from 9.99 to 0.33) are synthesized and analysed by H-1 and C-13 NMR in DMSO-d(6) and UV-Vis spectroscopy in CH2Cl2, CH3CN and DMSO. The UV spectra of complexes with medium-strong phenols show separate absorptions for A-HE and A-(HB)-B-... species. The prototropic equilibrium is also confirmed by sigmoidal plots of proton and carbon chemical shifts of the N+CH2 group versus pK(a) values of phenols. The effects of solvent polarity and excess of base on an acid-base equilibrium are discussed. (C) 2001 Elsevier Science B.V. All rights reserved.

引用

页码：17 / 23

页数：7

共 24 条

[11] King GSD., 1991, INTERMOLECULAR FORCE, P451, DOI 10.1007/978-3-642-76260-4_20
[12] Levy G.C., 1980, CARBON 13 NUCL MAGNE
[13] CHLORINE-35 NUCLEAR-QUADRUPOLE RESONANCE AND INFRARED SPECTROSCOPIC STUDIES OF HYDROGEN-BONDING IN COMPLEXES OF DICHLOROACETIC ACID WITH NITROGEN AND OXYGEN BASES - CORRELATION OF SPECTROSCOPIC PROPERTIES WITH PROTON AFFINITY AND AQUEOUS P-KAPPA-A
NOGAJ, B
DULEWICZ, E
BRYCKI, B
HRYNIO, A
BARCZYNSKI, P
DEGASZAFRAN, Z
SZAFRAN, M
KOZIOL, P
KATRITZKY, AR
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (04) : 1279 - 1285
[14] RATAJCZAK H, 1982, MOL INTERACTIONS, V3
[15] RATAJCZAK H, 1981, MOL INTERACTIONS, V2
[16] Ratajczak H., 1980, Molecular Interactions, V1
[17] SCHUSTER P, 1976, HYDROGEN BONDS RECEN, V1
[18] Serjeant E. P., 1979, IONISATION CONSTANTS
[19] Molecular structures and hydrogen bonding in the 1:1 and 1:2 complexes of pyridine betaine with 2,6-dichloro-4-nitrophenol; an example of strongly coupled hydrogen bonds, O-H-O=C-O-H-O-
Szafran, M
DegaSzafran, Z
Buczak, G
Katrusiak, A
Potrzebowski, MJ
Komasa, A
[J]. JOURNAL OF MOLECULAR STRUCTURE, 1997, 416 (1-3) : 145 - 160
[20] REACTION OF BETAINES WITH PHENYL ISOCYANATE - REACTIONS WITH BETAINE .3.
WITTMANN, H
BEUTEL, P
ZIEGLER, E
[J]. MONATSHEFTE FUR CHEMIE, 1969, 100 (04): : 1362 - &

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