NMR and UV Study of 1,1′-(α,ω-Alkanediyl)bis[thymine] and l,1′-(α,ω-Alkanediyl)bis[uracil]

Article abstract of DOI:10.1246/bcsj.70.2239

Treatment of thymine or uracil with Br(CH₂)_nBr (n = 3-10) in the presence of t-BuOK gave 1,1′-(α,ω-alkanediyl)bis[thymine] or 1,1′-(α,ω-alkanediyl)bis[uracil] together with l-(ω-bromoalkyl)thymine or l-(ω-bromoalkyl)uracil. The structures of these products were determined on the basis of the coupling constants between 5- and 3-positions of uracil ring on the ¹H NMR spectra. Molecular aggregation of the thymine and uracil rings of these compounds in aqueous solution was studied on the basis of their ¹H NMR and UV spectra. A stacking interaction of the two thymine rings linked by shorter polymethylene chains such as trimethylene and tetramenthylene groups was observed.