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Gas‐Phase Reactivity of Uracil, 2‐Thiouracil, 4‐Thiouracil, and 2,4‐Dithiouracil towards the Cu + Cation: A DFT Study
Author(s) -
Lamsabhi Al Mokhtar,
Alcamí Manuel,
Mó Otilia,
Yáñez Manuel
Publication year - 2003
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.200300704
Subject(s) - heteroatom , chemistry , tautomer , uracil , isomerization , thiouracil , reactivity (psychology) , adduct , thio , density functional theory , chalcogen , medicinal chemistry , crystallography , computational chemistry , organic chemistry , catalysis , medicine , ring (chemistry) , dna , biochemistry , alternative medicine , thyroid , pathology
80 Cu + –(thio)uracil structures were investigated by DFT calculations, which, with the exception of 2‐thiouracil, showed that attachment of the Cu + cation occurs initially at the heteroatom at position 4. For uracil–Cu + , 2‐thiouracil–Cu + , and 2,4‐dithiouracil–Cu + in the global minimum the Cu + cation bridges the heteroatom at position 2 and an adjacent amino group of the corresponding enolic tautomer. Isomerization processes leading from the most stable adduct to the global minimum (shown for 2‐thiouracil in the picture, with energies in kJ mol −1 ) and to other stable conformers were also investigated.