有機化合物の互変異性研究法の最近の進歩

概要

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Recent progress in spectroscopic and physicochemical methods to study the tautomerism of organic compounds has been reviewed. 15N-NMR has been recently applied to the study of tautomerism and proved to be a very useful technique to investigate the tautomeric behavior of nitrogen heterocycles including nucleic acid components owing to a wide chemical shift range (500 ppm). It is possible to analyze the tautomeric equilibrium quantitatively by using coupling constants of 15N-NMR. Photoelectron spectroscopy and ion cyclotron resonance technique are convenient for the investigation in gas phase. Measurement of the heat of solution in several organic solvents are useful tools for the study of highly biased equilibrium systems in non-aqueous solvents. Tautomeric equilibria are very sensitive to solvents and can be used as probes to estimate the solvent polarity and the polarity in the active site of enzymes. DNMR method, measurement of relaxation time, and temperaturejump method are available for. the study of kinetics of tautomeric interconversion. These methods are illustrated by some examples reported recently.
社団法人有機合成化学協会の論文