Title

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.

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.

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