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Organic & Biomolecular Chemistry Vol - 5 Issue - 9

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A theoretical study of hydration effects on the prototropic tautomerism of selenouracils

Content Provider	Royal Society of Chemistry (RSC)
Author	Mó, Otilia Trujillo, Cristina Yáñez, Manuel
Copyright Year	2007
Abstract	The prototropic tautomerism of 2-, 4-selenouracil and 2,4-diselenouracil has been studied using density functional theory (DFT) methods, at the B3LYP/6–311 + G(3df,2p)//B3LYP/6–31G(d,p) level. The relative stability order of selenouracil tautomers does not resemble that of uracil tautomers, but it is similar to that of thiouracils, even though the energy gaps between the different tautomers of selenouracils are smaller than for thiouracils. The tautomerism activation barriers are high enough as to conclude that only the oxo-selenone or the diselenone structures should be found in the gas phase. The specific interaction with one water molecule reduces these barriers by a half, but still the oxo-selenone form is always the most stable tautomer. The addition of a second water molecule has a relatively small effect, as well as bulk effects, evaluated by means of a continuum-polarized model. For isolated 2- and 4-selenouracils, the more favorable tautomerization process corresponds to a hydrogen transfer towards the selenium atom, the activation barriers for transfer towards the oxygen atom being much higher. This situation changes when specific and bulk effects are included, and the latter process becomes the more favorable one. For 2,4-diselenouracil the more favorable tautomerization, in the gas phase, corresponds to the H shift from N1 to the Se atom at C2, while solvation effects favor the transfer from N3 to the Se atom at C4.
Starting Page	3092
Ending Page	3099
Page Count	8
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	5
Issue Number	19
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b708045j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Oxygen Solvation Density functional theory SoltyRei Tautomer Selenium Uracil Hydrogen bond
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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