Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling

L.H. Koole, Hans Boer, de, J.W. Haan, de, C.A.G. Haasnoot, P. Dael, van, H.M. Buck

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Abstract

A completely rigid conformation is found for the syn-nucleoside 8-bromo-2,3-O-isopropylidene-adenosine in apolar solvents, which is due to an effective O(5)–H N(3) hydrogen bond, as is demonstrated by a substantial N(3) quadrupolar broadening of the H(5) resonances in the 1H n.m.r. spectra.
Original languageEnglish
Pages (from-to)362-364
JournalJournal of the Chemical Society, Chemical Communications
Issue number4
DOIs
Publication statusPublished - 1986

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