Article
Single- and Double-Proton-Transfer in the Aggregate between Cytosine and Guaninediazonium Ion
Organic Letters
Abstract
The structure of "guaninediazonium ion" in its aggregate with cytosine has been explored with ab initio and density functional methods. The hydroqen-bonded aggregate between cytosine and guaninediazonium ion, 1, is a stable minimum, 3. While the isolated enol tautomer of guaninediazonium ion, 2, is significantly more stable than 1, the tautomeric aggregate 4 that results from double-proton-transfer in 3 is almost isoenergetic with 3. Most interesting and entirely unexpected is the finding that neither 3 nor 4 is predicted to be the thermodynamically predominant structure. Instead, single-proton-transfer to cytosine results in the most stable cytosinium-guaninediazo complex, 5.
Department(s)
Chemistry
Keywords and Phrases
- cytosine,
- diazonium compound,
- DNA,
- drug derivative,
- guanine,
- guaninediazonium,
- proton,
- chemistry,
- conformation,
- hydrogen bond,
- thermodynamics,
- Cytosine,
- Diazonium Compounds,
- DNA,
- Guanine,
- Hydrogen Bonding,
- Molecular Conformation,
- Protons,
- Thermodynamics
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 1999 American Chemical Society (ACS), All rights reserved.
Publication Date
6-1-1999
Publication Date
01 Jun 1999
Disciplines
Citation Information
Rainer Glaser and Michael A. Lewis. "Single- and Double-Proton-Transfer in the Aggregate between Cytosine and Guaninediazonium Ion" Organic Letters Vol. 1 Iss. 2 (1999) p. 273 - 276 ISSN: 1523-7060 Available at: http://works.bepress.com/rainer-glaser/114/