The conformations of 1,4-butanedioic acid as a function of solvent polarity in a series of alcohols as determined by NMR spectroscopy

被引：14

作者：

Williams, LN ^{[1
]}

Petterson, KA ^{[1
]}

Roberts, JD ^{[1
]}

机构：

[1] CALTECH, Gates & Crellin Labs Chem, Pasadena, CA 91125 USA

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2002年 / 106卷 / 33期

关键词：

D O I：

10.1021/jp013220n

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：

Vicinal proton-proton NMR couplings have been employed to estimate the differences in conformational equilibria for 1,4-butanedioic-2,3-C-13(2) acid in the progression of its diprotic to monoprotic to di-ionized forms as a function of solvent in water and in a series of alcohols ranging from methanol to tert-butyl alcohol. Except for. water, the percentage of gauche increases from diacid to monoanion and then decreases from monoanion to dianion. The substantial gauche preference for the monoanion species in the less-polar alcohols is clearly the result of intramolecular hydrogen bonding.

引用

页码：7491 / 7493

页数：3

共 11 条

[1] EMPIRICAL GROUP ELECTRONEGATIVITIES FOR VICINAL NMR PROTON-PROTON COUPLINGS ALONG A C-C BOND - SOLVENT EFFECTS AND REPARAMETERIZATION OF THE HAASNOOT EQUATION [J].

ALTONA, C ;

FRANCKE, R ;

DEHAAN, R ;

IPPEL, JH ;

DAALMANS, GJ ;

HOEKZEMA, AJAW ;

VANWIJK, J .

MAGNETIC RESONANCE IN CHEMISTRY, 1994, 32 (11) :670-678

[2] RELATIONSHIP BETWEEN PROTON PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .5. EMPIRICAL SUBSTITUENT CONSTANTS DEDUCED FROM ETHANES AND PROPANES [J].

ALTONA, C ;

IPPEL, JH ;

HOEKZEMA, AJAW ;

ERKELENS, C ;

GROESBEEK, M ;

DONDERS, LA .

MAGNETIC RESONANCE IN CHEMISTRY, 1989, 27 (06) :564-576

[3]

BOTHNERBY AA, 1968, COMPUTER PROGRAMS CH, V1, P10

[4]

CHOI PJ, 2002, IN PRESS J PHYS ORG

[5]

GREGOREVA AA, 1970, ZH FIZ KHIM, V44, P440

[6] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].

HAASNOOT, CAG ;

DELEEUW, FAAM ;

ALTONA, C .

TETRAHEDRON, 1980, 36 (19) :2783-2792

[7]

KENT DR, 2002, IN PRESS J AM CHEM S

[8] TITRATION OF DIPROTIC ACIDS IN ALCOHOLS AND INTRA-MOLECULAR HYDROGEN-BONDING IN MONO-ANIONS WITH EMPHASIS ON ISOPROPANOL AND TERT-BUTANOL [J].

KOLTHOFF, IM ;

CHANTOONI, MK .

ANALYTICAL CHEMISTRY, 1978, 50 (11) :1440-1446

[9] CONFORMATIONAL-CHANGES OF BUTANEDIOIC ACID AS A FUNCTION OF PH AS DETERMINED FROM CHANGES IN VICINAL PROTON-PROTON NMR COUPLINGS [J].

LIT, ES ;

MALLON, FK ;

TSAI, HY ;

ROBERTS, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9563-9567

[10]

PETTERSON K, 2001, UNPUB NMR DETERMINAT

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