Morin, FG
1989
Use of Carbon-13 Nuclear Magnetic Resonance in Conformational Analysis of Hydroaromatic Compounds, in Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds
Morin, F.G. and Grant, D.M.
VCH Publishers, New York, Peter W. Rabideau (Editor), 1989 (In press). Funded by National Institutes of Health.
Since the original observation or nuclear magnetic resonance (NMR), the technique of solution-state NMR has become a premier method of structural and conformational analysis of organic molecules. With the introduction of Fourier transform methods, C-13-NMR has exceeded H-1-NMR as a tool for conformational analysis and a number of books have become standard reference texts in this field.
The chemical shift experienced by a C-13 nucleus is determined by several electronic factors such as hybridization and inductive effects of substituents. Relatively smaller but highly informative changes in chemical shift result from even subtle changes in conformation, for example, the difference in shift of an equatorial and an axial methyl group in methylcyclohexane. The utility of conformationally dependent C-13 shifts in hydroaromatic compounds is the focus of this chapter.
Hydroaromatic compounds such as terralin (1,2,3,4-tetrahydronaphthalene), while of significant importance in the field of fuel science as reactive components in the liquefaction and gasification of coals, have not received their share of NMR attention over the years compared with the well-studied and understood saturated ring systems such as cyclohexane. These mixed cyclic systems (both aromatic and aliphatic) possess interesting differences compared with either the pure aliphatic or aromatic ring systems. Therefore, a good understanding of the conformational properties and the energetics involved in these compounds would be valuable. An organized and systematic study of the conformationally dependent C-13 chemical shifts of these molecules is aided by the use of a multiparameter regression analysis. To introduce this technique and to provide a comparison of the conformational properties of the cyclohexanes with hydroaromatics, we begin with a brief historical review of the use of C-13 chemical shifts in the conformational analysis of alkanes and cyclohexanes.
Morin, FG
1989
Use of Carbon-13 Nuclear Magnetic Resonance in Conformational Analysis of Hydroaromatic Compounds, in Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds
Morin, F.G. and Grant, D.M.
VCH Publishers, New York, Peter W. Rabideau (Editor), 1989 (In press). Funded by National Institutes of Health.
Since the original observation or nuclear magnetic resonance (NMR), the technique of solution-state NMR has become a premier method of structural and conformational analysis of organic molecules. With the introduction of Fourier transform methods, C-13-NMR has exceeded H-1-NMR as a tool for conformational analysis and a number of books have become standard reference texts in this field.
The chemical shift experienced by a C-13 nucleus is determined by several electronic factors such as hybridization and inductive effects of substituents. Relatively smaller but highly informative changes in chemical shift result from even subtle changes in conformation, for example, the difference in shift of an equatorial and an axial methyl group in methylcyclohexane. The utility of conformationally dependent C-13 shifts in hydroaromatic compounds is the focus of this chapter.
Hydroaromatic compounds such as terralin (1,2,3,4-tetrahydronaphthalene), while of significant importance in the field of fuel science as reactive components in the liquefaction and gasification of coals, have not received their share of NMR attention over the years compared with the well-studied and understood saturated ring systems such as cyclohexane. These mixed cyclic systems (both aromatic and aliphatic) possess interesting differences compared with either the pure aliphatic or aromatic ring systems. Therefore, a good understanding of the conformational properties and the energetics involved in these compounds would be valuable. An organized and systematic study of the conformationally dependent C-13 chemical shifts of these molecules is aided by the use of a multiparameter regression analysis. To introduce this technique and to provide a comparison of the conformational properties of the cyclohexanes with hydroaromatics, we begin with a brief historical review of the use of C-13 chemical shifts in the conformational analysis of alkanes and cyclohexanes.