LONG-RANGE DEUTERIUM-ISOTOPE EFFECTS ON C-13 NMR SHIFTS OF INTRAMOLECULARLY HYDROGEN-BONDED 9-HYDROXYPHENALEN-1-ONES

被引:25
作者
ENGDAHL, C
GOGOLL, A
EDLUND, U
机构
[1] UNIV UPPSALA,DEPT ORGAN CHEM,BOX 531,S-75121 UPPSALA,SWEDEN
[2] UMEA UNIV,DEPT ORGAN CHEM,NMR RES GRP,S-90187 UMEA,SWEDEN
关键词
PRIMARY ISOTOPE EFFECT; SECONDARY ISOTOPE EFFECT; EQUILIBRIUM ISOTOPE EFFECT; SELECTIVE INEPT; 2D NMR; HETCOR; REYCOR; COLOC-S; HMQC;
D O I
10.1002/mrc.1260290112
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The H-1 and C-13 NMR spectra of 9-hydroxyphenalenone (1) and 9-hydroxy-2-methylphenalenone (2) have been completely assigned. Primary and secondary deuterium isotope effects were determined in three solvents (chloroform, acetone and dimethyl sulphoxide), including the effect of temperature on the secondary isotope effects. Both negative and large long-range secondary isotope effects were found for both 1 and 2. The average secondary isotope effects for corresponding carbons follow the same sign and magnitude pattern in both compounds.
引用
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页码:54 / 62
页数:9
相关论文
共 34 条
[1]   PROTON, DEUTERIUM, AND TRITIUM NUCLEAR MAGNETIC-RESONANCE OF INTRA-MOLECULAR HYDROGEN-BONDS - ISOTOPE EFFECTS AND SHAPE OF POTENTIAL-ENERGY FUNCTION [J].
ALTMAN, LJ ;
LAUNGANI, D ;
GUNNARSSON, G ;
WENNERSTROM, H ;
FORSEN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (26) :8264-8266
[3]   CORRELATION OF PROTON CHEMICAL-SHIFTS BY TWO-DIMENSIONAL FOURIER-TRANSFORM NMR [J].
BAX, A ;
FREEMAN, R ;
MORRIS, G .
JOURNAL OF MAGNETIC RESONANCE, 1981, 42 (01) :164-168
[5]   PRACTICALITIES AND APPLICATIONS OF REVERSE HETERONUCLEAR SHIFT CORRELATION - PORPHYRIN AND POLYSACCHARIDE EXAMPLES [J].
CAVANAGH, J ;
HUNTER, CA ;
JONES, DNM ;
KEELER, J ;
SANDERS, JKM .
MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (10) :867-875
[6]   ROLE OF SYMMETRY IN THE TUNNELLING OF THE PROTON IN DOUBLE MINIMUM POTENTIALS [J].
DELAVEGA, JR .
ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (06) :185-191
[7]   SYMMETRY AND TUNNELING IN THE INTRAMOLECULAR PROTON-EXCHANGE IN NAPHTHAZARIN, METHYLNAPHTHAZARIN, AND DIMETHYLNAPHTHAZARINS [J].
DELAVEGA, JR ;
BUSCH, JH ;
SCHAUBLE, JH ;
KUNZE, KL ;
HAGGERT, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) :3295-3299
[8]   NUCLEAR MAGNETIC-RESONANCE STUDY OF INTRAMOLECULAR HYDROGEN-BOND IN ACETYLACETONE [J].
EGAN, W ;
GUNNARSSON, G ;
BULL, TE ;
FORSEN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (14) :4568-4572
[9]   PROTON AND DEUTERON MAGNETIC RESONANCES OF THE STRONGLY HYDROGEN-BONDED COMPLEXES (HCO2)2H- AND (HCO2)2D- IN AQUEOUS-SOLUTION - THE PRIMARY ISOTOPE EFFECT ON CHEMICAL-SHIFT, AND ISOTOPIC FRACTIONATION OF LABILE HYDROGEN IN H-D MIXTURES [J].
FENN, MD ;
SPINNER, E .
JOURNAL OF PHYSICAL CHEMISTRY, 1984, 88 (18) :3993-3997
[10]   PROTON AND DEUTERIUM NMR OF HYDROGEN-BONDS - RELATIONSHIP BETWEEN ISOTOPE-EFFECTS AND HYDROGEN-BOND POTENTIAL [J].
GUNNARSSON, G ;
WENNERSTROM, H ;
EGAN, W ;
FORSEN, S .
CHEMICAL PHYSICS LETTERS, 1976, 38 (01) :96-99