Single- and Double-Proton-Transfer in the Aggregate between Cytosine and Guaninediazonium Ion
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.
Recommended Citation
R. Glaser and M. A. Lewis, "Single- and Double-Proton-Transfer in the Aggregate between Cytosine and Guaninediazonium Ion," Organic Letters, vol. 1, no. 2, pp. 273 - 276, American Chemical Society (ACS), Jun 1999.
The definitive version is available at https://doi.org/10.1021/ol990589a
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
International Standard Serial Number (ISSN)
1523-7060
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 1999 American Chemical Society (ACS), All rights reserved.
Publication Date
01 Jun 1999
