N-alkenyl amide rotational barriers by 2D EXSY NMR

被引:17
作者
Aguirre, G
Somanathan, R [1 ]
Hellberg, LH
Dwyer, TJ
North, R
机构
[1] San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
[2] Inst Tecnol Tijuana, Ctr Grad Invest, Mexico City 22000, DF, Mexico
关键词
NMR; 2D EXSY NMR; conformation; N-alkenylamides; E/Z rotation barriers;
D O I
10.1002/mrc.1142
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The rotational barriers of some N-alkenylamides were measured by 2D exchange spectroscopy (2D EXSY) NMR techniques. It was found that the conjugated double bond lowers E,Z barriers by 2.6 kJ mol(-1). Copyright (C) 2003 John Wiley Sons, Ltd.
引用
收藏
页码:131 / 134
页数:4
相关论文
共 23 条
[1]   Synthesis of some fluorinated N-alkenyl amides [J].
Aguirre, G ;
Somanathan, R ;
Hellberg, LH .
JOURNAL OF FLUORINE CHEMISTRY, 1998, 90 (01) :5-8
[2]   SYNTHESIS OF ENAMIDES [J].
BRETTLE, R ;
MOSEDALE, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2185-2195
[3]   ISOLATION AND STRUCTURE OF TUNICHROME B-1, A REDUCING BLOOD PIGMENT FROM THE TUNICATE ASCIDIA-NIGRA L [J].
BRUENING, RC ;
OLTZ, EM ;
FURUKAWA, J ;
NAKANISHI, K ;
KUSTIN, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) :5298-5300
[4]  
COSSIO FP, 2000, EUR J ORG CHEM, P2497
[5]   Rotational barriers in push-pull ethylenes: An advanced physical-organic project including 2D EXSY and computational chemistry [J].
Dwyer, TJ ;
Norman, JE ;
Jasien, PG .
JOURNAL OF CHEMICAL EDUCATION, 1998, 75 (12) :1635-1640
[6]  
Eliel E. L., 1994, STEREOCHEMISTRY ORGA, P540
[7]   A STUDY OF HINDERED INTERNAL ROTATION IN SOME N-VINYL-SUBSTITUTED AMIDES BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY [J].
GEHRING, DG ;
MOSHER, WA .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (10) :3436-&
[8]  
Gromova M, 2000, EUR J INORG CHEM, P545
[9]   Terpeptin, a novel mammalian cell cycle inhibitor, produced by Aspergillus terreus 95F-1 [J].
Kagamizono, T ;
Sakai, N ;
Arai, K ;
Kobinata, K ;
Osada, H .
TETRAHEDRON LETTERS, 1997, 38 (07) :1223-1226
[10]   INDOLE ALKALOIDS FROM THE MARINE RED ALGA MARTENSIA-FRAGILIS [J].
KIRKUP, MP ;
MOORE, RE .
TETRAHEDRON LETTERS, 1983, 24 (20) :2087-2090