2001
DOI: 10.1021/jp0019411
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Theoretical Study of Uracil Tautomers. 2. Interaction with Water

Abstract: The interaction of 2-hydroxy, 4-hydroxy, and 2,4-dihydroxy tautomers of uracil with a water molecule is studied at the B3LYP/6-31+G(d,p) computational level. Depending on the nature of the tautomers, cyclic or open structures are formed. In most of the cyclic structures, water accepts the OH or NH protons and donates its proton to the O or N atoms of the uracil tautomers. Two anticooperative structures where water acts as a biacceptor are also formed. The intermolecular distances, binding energies, and frequen… Show more

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Cited by 101 publications
(118 citation statements)
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“…The most stable structure of the uracil-water cluster is that in which the water molecule forms a bridge between O4 and N3(H) of U1. [41,44] This configuration is favorable for a potentially water-catalyzed double proton transfer between U1 and U2. The corresponding transition state is hexahedric, with the water molecule acting as a bridge.…”
Section: Discussionmentioning
confidence: 99%
“…The most stable structure of the uracil-water cluster is that in which the water molecule forms a bridge between O4 and N3(H) of U1. [41,44] This configuration is favorable for a potentially water-catalyzed double proton transfer between U1 and U2. The corresponding transition state is hexahedric, with the water molecule acting as a bridge.…”
Section: Discussionmentioning
confidence: 99%
“…[9] Since then, considerable theoretical studies have been performed to explore protontransfer reactions for isolated and solvated bases and base pairs in their neutral ground electronic states, [10][11][12][13][14][15][16] their excited electronic states [17] and their anionic/cationic states, [18][19][20][21] which may be in connection with spontaneous, photoinduced and radiation-induced DNA damages, respectively.…”
Section: Introductionmentioning
confidence: 99%
“…The effect of hydration of the DNA bases is very local and only a limited number of water molecules contribute to it significantly [1,2]. Many studies on the gas-phase interactions of neutral and anionic forms of nucleic acid bases [3][4][5][6][7][8][9][10][11][12][13] [19] of hydrated adenine and thymine cations. Much less attention has been paid to the hydration of protonated DNA components, although these forms are of considerable interest in view of their potential formation in radiation-induced damage of DNA and RNA, and interaction with a water environment.…”
mentioning
confidence: 99%
“…The effect of hydration of the DNA bases is very local and only a limited number of water molecules contribute to it significantly [1,2]. Many studies on the gas-phase interactions of neutral and anionic forms of nucleic acid bases [3][4][5][6][7][8][9][10][11][12][13] and nucleosides [14] with water molecules have been performed theoretically. A few experimental studies have been carried out on hydration enthalpies [15], IR spectra [13], UV spectra [16], hydration dynamics [17] of DNA bases, ionization potentials [18], and metastable decay [19] of hydrated adenine and thymine cations.…”
mentioning
confidence: 99%