CONFORMATIONAL STUDIES OF 2-METHYL-3-PHENYLPROPIONIC ACID, 2-PHENYLBUTYRIC ACID AND THEIR METHYL-ESTERS BY NMR-SPECTROSCOPY

被引:12
作者
SPASSOV, SL
STEFANOVA, R
机构
[1] Institute of Organic Chemistry, Bulgarian Academy of Sciences
关键词
D O I
10.1016/0022-2860(79)80344-0
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
The conformational distribution of PhCH2CH(CH3)COOR and CH3CH2CH(Ph)COOR (R = H, CH3) has been studied by NMR spectroscopy. In the former case the conformer with the phenyl and carboxyl (or methoxycarbonyl) groups in the anti position relative to each other is favoured. For 2-phenylbutyric acid and its ester the forms with the methyl group gauche to phenyl or COOR are almost equally represented. The validity of the additive gauche-interaction scheme for prediction of conformational distribution in substituted ethanes is also discussed. © 1979.
引用
收藏
页码:219 / 224
页数:6
相关论文
共 11 条
[1]   ROTATIONAL-ISOMERISM .21. CONFORMATION OF 2-AMINO-3-FLUOROPROPANOIC ACID (2-AFP) AND 2-FLUORO-3-AMINOPROPANOIC ACID (3-AFP) AS ZWITTERION, CATION AND ANION, AN NMR AND MO STUDY [J].
ABRAHAM, RJ ;
LOFTUS, P ;
THOMAS, WA .
TETRAHEDRON, 1977, 33 (10) :1227-1234
[2]   NUCLEAR MAGNETIC-RESONANCE SPECTRA OF TROPIC ACID AND SOME DERIVATIVES [J].
DIMITROV, VS ;
SPASSOV, SL ;
RADEVA, TZ .
JOURNAL OF MOLECULAR STRUCTURE, 1975, 27 (01) :167-176
[3]   A CONVENIENT METHOD FOR REDUCTION OF ALPHA,BETA UNSATURATED CARBOXYLIC ACIDS [J].
HJELTE, NS .
ACTA CHEMICA SCANDINAVICA, 1961, 15 (05) :1200-&
[4]  
MARCHESE G, 1975, J CHEM SOC P2, V2, P1100
[5]  
RUPE H, 1909, ANNALEN, V369, P332
[7]   COMPLETE CONFORMATIONAL ANALYSIS OF 3-PHENYLPROPANOL [J].
SNYDER, EI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (10) :2579-&
[8]   CONFORMATIONAL STUDIES OF SOME 2-PHENYLPROPYL DERIVATIVES BY NMR-SPECTROSCOPY AND USE OF LANTHANIDE SHIFT-REAGENTS [J].
SPASSOV, SL ;
STEFANOVA, R .
JOURNAL OF MOLECULAR STRUCTURE, 1977, 42 (DEC) :109-115
[9]   NMR-STUDIES OF 3-PHENYLBUTYRIC ACID AND ITS METHYL-ESTER - POSSIBLE APPROACH FOR CONFORMATIONAL-ANALYSIS USING LANTHANIDE SHIFT-REAGENTS [J].
SPASSOV, SL ;
STEFANOVA, R ;
LADD, JA .
JOURNAL OF MOLECULAR STRUCTURE, 1977, 36 (01) :93-100
[10]   NMR-SPECTRA AND CONFORMATION OF 1,2-DIPHENYLPROPANE AND 2,3-DIPHENYLPROPANOIC ACID [J].
SPASSOV, SL ;
ORAHOVAT.AS ;
MISHEV, SM ;
SCHRAML, J .
TETRAHEDRON, 1974, 30 (02) :365-368