Title

Nitrosative Adenine Deamination: Facile Pyrimidine Ring-Opening in the Dediazoniation of Adeninediazonium Ion

Abstract

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.

Department(s)

Chemistry

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)

1523-7060

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2003 American Chemical Society (ACS), All rights reserved.

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