Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. I. The Ionization Constants in Aqueous Solution
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概要
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The ionization constants of 5-substituted 4-hydroxy-2-methylpyrimidines (1-11) and some of their methyl derivatives, 4-methoxy-2-methylpyrimidines, 1,2-dimethyl-4 (1H)-pyrimidones and 2,3-dimethyl-4 (3H)-pyrimidones were determined. From the ionization constants, the degree of lactim-lactam tautomerism in the 4-hydroxypyrimidines was estimated. It was found that each of the pyrimidines exist mainly as a mixture of lactam forms (4 (1H)-pyrimidone and 4 (3H)-pyrimidone) in approximately equal amounts, in aqueous solution (ca. 1×10^<-4>M). The results were also supported by ultraviolet absorption spectroscopy. The substituent effect on the tautomerism was discussed in connection with the Hammett equation for the basicity of the pyrimidines.
- 公益社団法人日本薬学会の論文
- 1974-06-25
著者
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北川 隆康
Shionogi Research Laboratories Shionogi & Co. Ltd.
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水上 聰
Shionogi Research Laboratory Shionogi And Co. Ltd.
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北川 隆康
塩野義製薬(株)研究所
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平井 瑛三
Shionogi Research Laboratories Shionogi & Co. Ltd.
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