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NMR and X-ray structural studies on 3-benzyl-8-bromoadenine

✍ Scribed by Huey-San Melanie Siah; Carl Henrik Görbitz; Lise-Lotte Gundersen


Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
305 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

8‐Bromoadenine was benzylated in the presence of base to give a mixture of two regioisomers. One was easily recognized as 9‐benzyl‐8‐bromoadenine, but the other structure could not be determined with absolute certainty by NMR. Therefore, X‐ray crystallography was used to prove that the benzyl group was attached to N‐3. Furthermore, it is shown that the 3‐benzyl adenine derivative exists as the amine tautomer both in the crystalline state as well as in solution (DMSO‐d~6~), with restricted rotation around the N^6^C6 bond. J. Heterocyclic Chem., (2011).


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