Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Kinetic and NMR Spectroscopic Studies of the Fusion Reactions of Chloropurines with 1,2,3,5-Tetra-O-acetyl-D-ribofuranoses
Akira HosonoKiyohisa FujiiToshizo TadaHisayuki TanakaYohko OhgoYoshiharu IshidoTetsuo Sato
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1973 Volume 46 Issue 9 Pages 2814-2820

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Abstract

A kinetic study of the fusion reaction and the reaction in dimethyl sulfoxide of 2,6-dichloropurine with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose was undertaken, and both of them were proved to be of the second order. The activation energy and the activation entropy of the reaction in dimethyl sulfoxide were obtained: Ea=38.0 kcal/ mol and ΔS\ eweq=+15.3 cal · mol. The reaction was thus concluded to be bimolecular involving a considerable unimolecular character. Subsequently, the fusion reactions of 2,6-dichloro- and 2,6,8-trichloropurine with 1,2,3,5-tetra-O-acetyl-α- and -β -D-ribofuranose were examined by NMR spectroscopy with respect to the relative content ratios of all the materials and products in each reaction mixture; the results were found to be in good agreement with those obtained by the above kinetic study. On the basis of these results, the mechanism of the fusion reaction was discussed.

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