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Tautomeric preferences and electron delocalization in biurets, thiobiurets, and dithiobiurets: An ab initio study by Legesse Adane; Prasad V. Bharatam is a Physics and Astronomy article available to read on EtoBox.

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## Abstract In several literature reports biuret and its sulfur analogs are reported to exist in their diketo form with general formula H~2~NCXNHCYNH~2~ (X = O, Y = O, biuret; X = Y = S, dithiobiuret; and X = O, Y = S, thiobiuret). On the other hand, recently reported results on the electronic structure of biguanide analogs (X = Y = NH)demonstrated that a form equivalent to diketo is not the preferred structure. Thus, a systematic __ab initio__ study on the tautomeric preferences of biuret and its sulfur analogs (dithiobiuret and thiobiuret) has been carried out. The results indicate that an interplay of conjugative stabilization and intramolecular hydrogen bonding to play a role in tautomeric preferences. Energy and geometric parameters, natural bond orbital analyses have been employed to understand the chemistry of the title compounds. The results indicate that unlike biguanides, these compounds prefer diketo forms containing hydrogen on the bridging nitrogen (N4) and in a __trans‐__arrangement (1a–4a). However, tautomerization of these keto forms to the corresponding enol isomers was also found to be highly probable. © 2008 Wiley Periodicals, Inc. Int J Quantum Chem, 2008

Who reads Tautomeric preferences and electron delocalization in biurets, thiobiurets, and dithiobiurets: An ab initio study?

Author

Legesse Adane; Prasad V. Bharatam

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0020-7608)

Published

2008

Language

EN

Field

Physics and Astronomy (Physical Sciences)