Article
Nitrosative Adenine Deamination: Facile Pyrimidine Ring-Opening in the Dediazoniation of Adeninediazonium Ion
Organic Letters
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
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2003 American Chemical Society (ACS), All rights reserved.
Publication Date
10-1-2003
Publication Date
01 Oct 2003
Disciplines
Citation Information
Brian Hodgen, Sundeep Rayat and Rainer Glaser. "Nitrosative Adenine Deamination: Facile Pyrimidine Ring-Opening in the Dediazoniation of Adeninediazonium Ion" Organic Letters Vol. 5 Iss. 22 (2003) p. 4077 - 4080 ISSN: 1523-7060 Available at: http://works.bepress.com/rainer-glaser/87/