ROTATIONAL-ISOMERISM IN 5-AMINO-6-(N-METHYLFORMAMIDO)-AS-TRIAZIN-3(2H)-ONE

被引:5
作者
RIAND, J
TANGUY, M
CHENON, MT
TZENG, CC
PANZICA, RP
机构
[1] CNRS,LASIR,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE
[2] UNIV RHODE ISL,DEPT MED CHEM,KINGSTON,RI 02881
[3] UNIV RHODE ISL,DEPT CHEM,KINGSTON,RI 02881
关键词
!sup]1[!/sup]H DNMR; 6‐Azapurin‐2‐ones; 6‐Azapyrimidin‐2‐ones; Rotational isomerism;
D O I
10.1002/mrc.1260280607
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A 1H dynamic NMR study of the hindered rotation in 5‐amino‐6‐(N‐methylformamido)‐as‐triazin‐3(2H)‐one was conducted. Signals for two rotamers were observed and their proton chemical shifts were assigned. It was found that the rotamer in which the as‐triazine ring is cis to the formyl hydrogen predominates. The free energies of activation for hindered rotations about the N CHO and C NH2 bonds were determined by 1H NMR line‐shape analysis. Copyright © 1990 John Wiley & Sons, Ltd.
引用
收藏
页码:505 / 509
页数:5
相关论文
共 26 条
[1]   TORSIONAL BARRIERS IN 6-AMINO-5-FORMAMIDOPYRIMIDIN-4(3H)-ONES [J].
BERGMANN, F ;
RAHAT, M ;
RABINOVITZ, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (10) :1141-1144
[2]  
BINSCH G, 1969, 140 IND U QUANT CHEM
[3]   DESICCANT EFFICIENCY IN SOLVENT DRYING .3. DIPOLAR APROTIC-SOLVENTS [J].
BURFIELD, DR ;
SMITHERS, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3966-3968
[4]   6-AZAPURINES .2. CRYSTAL AND MOLECULAR-STRUCTURE OF 8,9-DIMETHYL-6-AZAPURIN-2-ONE [J].
CHEER, CJ ;
KOKKOU, S ;
TZENG, CC ;
PANZICA, RP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (10) :1455-1457
[5]   DESCRIPTION OF OVERHAUSER EFFECT IN EXCHANGE SYSTEMS - APPLICATION TO CONFORMATIONAL ANALYSIS OF HETEROCYCLIC ALDEHYDES [J].
COMBRISSON, S ;
ROQUES, B ;
RIGNY, P ;
BASSELIER, JJ .
CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1971, 49 (06) :904-+
[6]   PROTON COUPLED C-13 MAGNETIC-RESONANCE SPECTRA - SIMPLE AMIDES [J].
DORMAN, DE ;
BOVEY, FA .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (09) :1719-1722
[7]  
EISTETTER K, 1973, CHEM BER-RECL, V106, P1389, DOI 10.1002/cber.19731060505
[8]   COMPARISON OF CHEMICAL EXCHANGE RATES DETERMINED BY NUCLEAR MAGNETIC RESONANCE LINE-SHAPE AND EQUILIBRATION METHODS . INTERNAL ROTATION OF N-METHYL-N-BENZYLFORMAMIDE [J].
GUTOWSKY, HS ;
JONAS, J ;
SIDDALL, TH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4300-&
[9]  
KATRITZKY AR, 1969, ORG MAGN RESONANCE, V1, P57