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NMR and X‐ray structural studies on 3‐benzyl‐8‐bromoadenine
Author(s) -
Siah HueySan Melanie,
Görbitz Carl Henrik,
Gundersen LiseLotte
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.733
Subject(s) - chemistry , tautomer , structural isomer , amine gas treating , derivative (finance) , crystallography , x ray , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , financial economics , economics , physics , quantum mechanics
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).