Synthesis, IR and NMR studies of zwitterionic ω-(1-pyrrolidine)alkanocarboxylic acids and their N-methyl derivatives

被引:18
作者
Dega-Szafran, Z [1 ]
Przybylak, R [1 ]
机构
[1] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
关键词
infrared spectroscopy; NMR spectroscopy; omega-(1-pyrrolidine)alkanocarboxylic acid salts; Zwitterionic compounds;
D O I
10.1016/S0022-2860(97)00119-1
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
Six omega-(1-pyrrolidine)alkanocarboxylic acid hydrohalides [C4H8N+H(CH2)(n)COOH . X-] and 1-(omega-carboxyalkyl)-1-methylpyrrolidinium hydrohalides [C4H8N+CH3(CH2)(n)COOH . X- (n = 1,2,3,4,5,10)] and their sodium and inner salts were synthesized, respectively. IR, H-1 and C-13 NMR spectra were analyzed with regard to the increasing distance effect on the interaction between the positive nitrogen atom with the negative carboxylic group. The configuration of the pyrrolidine ring was also discussed. (C) 1997 Elsevier Science B.V.
引用
收藏
页码:107 / 121
页数:15
相关论文
共 39 条
[31]  
STELLA VJ, 1987, Patent No. 4650803
[32]  
SZAFRAN M, UNPUB
[33]  
van Thoai N, 1965, COMPR BIOCHEM, V6, P208
[34]   THE SYNTHESES OF BETA-LACTAMS FROM ZINC ENOLATES OF N,N-DISUBSTITUTED ALPHA-AMINOACID ESTERS AND IMINES - SUBSTITUENT AND SOLVENT EFFECTS [J].
VANDERSTEEN, FH ;
KLEIJN, H ;
JASTRZEBSKI, JTBH ;
VANKOTEN, G .
TETRAHEDRON LETTERS, 1989, 30 (06) :765-768
[35]   EFFECT OF THE INTRAMOLECULAR CHARGE SEPARATION DISTANCE ON THE SOLUTION PROPERTIES OF BETAINES AND SULFOBETAINES [J].
WEERS, JG ;
RATHMAN, JF ;
AXE, FU ;
CRICHLOW, CA ;
FOLAND, LD ;
SCHEUING, DR ;
WIERSEMA, RJ ;
ZIELSKE, AG .
LANGMUIR, 1991, 7 (05) :854-867
[36]   CONFIGURATION OF NICOTINE - NUCLEAR MAGNETIC-RESONANCE STUDY [J].
WHIDBY, JF ;
SEEMAN, JI .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (09) :1585-1590
[37]   METHYL TRANSFER IN FIELD DESORPTION MASS-SPECTROMETRY OF AMMONIOALKANECARBOXYLATE HYDROCHLORIDE SALTS [J].
WOOD, GW ;
COLLACOTT, RJ .
ORGANIC MASS SPECTROMETRY, 1983, 18 (01) :42-45
[38]  
1977, BEILSTEINS HDB ORG C, V20, P205
[39]  
1977, BEILSTEINS HDB ORG C, V20, P211