Nitrosative Adenine Deamination: Facile Pyrimidine Ring-Opening in the Dediazoniation of Adeninediazonium Ion
Dediazoniation of adeninediazonium ion, 1, forms the heteroaromatic cation, 2. Ab initio studies at the CCSD(fc)/6-31G**/ /MP2(full)/6-31G** level now reveal that the cyclic cation 2 is kinetically and thermodynamically unstable with respect to the pyrimidine ring-opened cation, 3. The results suggest that 4-cyano-5-isocyano-imidazole, 4, and 4,5-dicyanoimidazole, 5, might be formed to some extent in nitrosative deaminations of adenine.
B. Hodgen et al., "Nitrosative Adenine Deamination: Facile Pyrimidine Ring-Opening in the Dediazoniation of Adeninediazonium Ion," Organic Letters, vol. 5, no. 22, pp. 4077-4080, American Chemical Society (ACS), Oct 2003.
The definitive version is available at https://doi.org/10.1021/ol035526d
Keywords and Phrases
4 cyano 5 isocyanoimidazole; 4 dicyanoimidazole; 4,5 dicyanoimidazole; 5 dicyanoimidazole; adenine derivative; imidazole derivative; pyrimidine derivative; unclassified drug; kinetics; nitrosation; ring opening; thermodynamics; Adenine; Deamination; Diazonium Compounds; Imidazoles; Models; Chemical; Models; Molecular; Molecular Structure; Thermodynamics
International Standard Serial Number (ISSN)
Article - Journal
© 2003 American Chemical Society (ACS), All rights reserved.
01 Oct 2003