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Isotopic Exchange of Hydrogen at C‐5 in Pyrimidine Derivatives: Tautomers with an sp 3 ‐Hybridised C‐5 Carbon Atom
Author(s) -
Dračínský Martin,
Holý Antonín,
Jansa Petr,
Kovačková Soňa,
Buděšínský Miloš
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900529
Subject(s) - chemistry , tautomer , protonation , carbon atom , deuterium , hydrogen atom , pyrimidine , hydrogen , hydrogen–deuterium exchange , medicinal chemistry , carbon fibers , proton , atom (system on chip) , stereochemistry , organic chemistry , ring (chemistry) , ion , physics , alkyl , materials science , quantum mechanics , composite number , computer science , composite material , embedded system
The proton‐to‐deuterium exchange reaction of the hydrogen atom at the 5‐position of 15 pyrimidine derivatives has been studied. The exchange proceeds under both acidic and alkaline conditions. Under acidic conditions, the mechanism involves protonation at the 5‐position (forming an σ complex), whereas under alkaline conditions the exchange is mainly a result of the formation of a tautomeric equilibrium, with one tautomer bearing an sp 3 ‐hybridised carbon atom at the 5‐position.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)