Conformations of N,N-diethyl-β-alanine and β-alanine as a function of solvent

被引：1

作者：

Piro, NA ^{[1
]}

Stein, RS ^{[1
]}

Roberts, JD ^{[1
]}

机构：

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

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2004年 / 17卷 / 05期

关键词：

N; N-diethyl-beta-alanine; beta-alanine; conformation; solvent;

D O I：

10.1002/poc.745

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conformational equilibria of N,N-diethyl-beta-alanine were estimated from vicinal proton-proton coupling constants between the -CH2-CH2- group in protic and aprotic solvents of different polarities. beta-Alanine was similarly studied in dimethyl sulfoxide (DMSO). In general, the results for both substances correspond fairly well with those reported earlier for beta-alanine in neutral and acidic aqueous solutions. There appeared to be little conformational preference for N,N-diethyl-beta-alanine in any of the solvents used, ranging from water to dichloromethane. The exception was a moderate preference (66-73%) for the trans conformer displayed by the conjugate base of N,N-diethyl-beta-alanine in all of the solvents studied. Copyright (C) 2004 John Wiley Sons, Ltd.

引用

页码：418 / 422

页数：5

共 13 条

[1] ROTATIONAL ISOMERISM .7. EFFECT OF SUBSTITUENT ON VICINAL COUPLING CONSTANTS IN XCH2.CH2Y FRAGMENTS [J].

ABRAHAM, RJ ;

GATTI, G .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (08) :961-&

[2] 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

[3] 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

[4]

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

[5] Effect of pH on the rotational conformations of 1,3-diamino-2-hydroxypropane [J].

Cheng, JM ;

Heller, JP ;

Petterson, KA ;

Roberts, JD .

MAGNETIC RESONANCE IN CHEMISTRY, 2002, 40 (10) :666-671

[6] Conformational equilibria of β-alanine and related compounds as studied by NMR spectroscopy [J].

Gregoire, F ;

Wei, SH ;

Streed, EW ;

Brameld, KA ;

Fort, D ;

Hanely, LJ ;

Walls, JD ;

Goddard, WA ;

Roberts, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7537-7543

[7] 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

[8] An NMR and quantum mechanical investigation of solvent effects on conformational equilibria of butanedinitrile [J].

Kent, DR ;

Dey, N ;

Davidson, F ;

Gregoire, F ;

Petterson, KA ;

Goddard, WA ;

Roberts, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (31) :9318-9322

[9] An NMR and quantum-mechanical investigation of tetrahydrofuran solvent effects on the conformational equilibria of 1,4-butanedioic acid and its salts [J].

Kent, DR ;

Petterson, KA ;

Gregoire, F ;

Snyder-Frey, E ;

Hanely, LJ ;

Muller, RP ;

Goddard, WA ;

Roberts, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4481-4486

[10] Nitromethane: The heat capacity of the gas, the vapor density, and the barrier to internal rotation [J].

Pitzer, KS ;

Gwinn, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :3313-3316

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