N-15 AND C-13 NMR-STUDY OF ACYLATED HYDRAZINES - THE INSTABILITY OF TRIFLUOROACETHYDRAZIDE IN THE SOLID-STATE

被引:24
作者
FRITZ, H [1 ]
KRISTINSSON, H [1 ]
MOLLENKOPF, M [1 ]
WINKLER, T [1 ]
机构
[1] CIBA GEIGY AG,CH-4002 BASEL,SWITZERLAND
关键词
!sup]13[!/sup]C–[!sup]1[!/sup]H coupling constants; !sup]15[!/sup]N NMR; !sup]15[!/sup]N‐[!sup]1[!/sup]H coupling constants; Hydrazides; Rotamer distribution;
D O I
10.1002/mrc.1260280410
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Trifluoroacethydrazide is unstable even in the solid state with respect to hydrazonium N,N′‐ditrifluoroacetyl hydrazinate, as shown by 15N and 13C NMR spectroscopy. The 1H, 13C and 15N NMR data and rotamer distributions of formyl‐, acet‐ and trifluoroacet‐hydrazide and of N,N′‐diformyl‐, N,N′‐diacetyl‐ and N,N′‐ditrifluoroacetyl‐hydrazine are reported and compared with the results of earlier investigations. A conformational dependence is observed for 1J(NH) and 2J(NH) in the formylhydrazides and of 1J(NH), 2J(NH) 3J(NH) in the N,N′‐diformylhydrazines. The conformational dependence of 2J(CH) in formamide, reported in the literature, however, could not be confirmed. Copyright © 1990 John Wiley & Sons, Ltd.
引用
收藏
页码:331 / 336
页数:6
相关论文
共 36 条
[1]   NUCLEAR MAGNETIC TRIPLE RESONANCE STUDIES ON FORMAMIDE N-14 [J].
BARBOIU, V ;
PETRESCU, V .
ORGANIC MAGNETIC RESONANCE, 1973, 5 (01) :43-45
[2]  
BISHOP GJ, 1967, J CHEM SOC CHEM COMM, P672
[3]  
BOUCHET P, 1972, B SOC CHIM FR, P2264
[4]   ELECTRONIC DELOCALIZATION IN N-C AND N-N BONDS [J].
BREMOND, M ;
MARTIN, GJ ;
WEBB, GA ;
REYNOLDS, DJ .
ORGANIC MAGNETIC RESONANCE, 1984, 22 (10) :640-648
[5]   SYNTHESIS OF 2,5 BIS(PERFLUOROALKYL)-1,3,4-OXADIAZOLES [J].
BROWN, HC ;
PILIPOVICH, D ;
CHENG, MT ;
PARCELL, LJ .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4407-&
[6]   SIGNS OF HETERONUCLEAR SPIN-SPIN COUPLING-CONSTANTS IN ACETAMIDE-N-15 [J].
DEMARCO, A ;
LLINAS, M .
ORGANIC MAGNETIC RESONANCE, 1979, 12 (08) :454-460
[7]   CONFORMATIONAL INTERCHANGE IN ACYCLIC HYDRAZINES [J].
DEWAR, MJS ;
JENNINGS, WB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (05) :1562-1569
[8]   APPLICATIONS OF N-15 NMR-SPECTROSCOPY TO THE STUDY OF UNSYMMETRICALLY N-SUBSTITUTED AMIDES AND MODEL PEPTIDE COMPOUNDS [J].
DORIE, J ;
GOUESNARD, JP ;
MECHIN, B ;
NAULET, N ;
MARTIN, GJ .
ORGANIC MAGNETIC RESONANCE, 1980, 13 (02) :126-131
[9]   PROTON COUPLED C-13 MAGNETIC-RESONANCE SPECTRA - SIMPLE AMIDES [J].
DORMAN, DE ;
BOVEY, FA .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (09) :1719-1722
[10]   EFFECT OF THE ORIENTATION OF SUBSTITUENTS ON THE CHEMICAL-SHIFTS OF C-13 .4. C-13 NMR-SPECTRA OF N,N-DIISOPROPYLAMIDES AND N,N-DITHIOAMIDES [J].
FRITZ, H ;
HUG, P ;
SAUTER, H ;
WINKLER, T ;
LAWESSON, SO ;
PEDERSEN, BS ;
SCHEIBYE, S .
ORGANIC MAGNETIC RESONANCE, 1981, 16 (01) :36-43