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• W4224277105 endingPage "106788" @default.
• W4224277105 startingPage "106788" @default.
• W4224277105 abstract "• Ionization changes xanthine-tautomers stability and electron delocalization. • Two NH tautomers (one dioxo and one hydroxy-oxo form) are favored for X + . • Tautomeric mixture of X − consists mainly of two dioxo CH tautomers. • IP and EA values of NH isomers are lower than those of CH tautomers. • Electron delocalization (measured by HOMED) is parallel to Δ G s only for dioxo isomers. The complete prototropic tautomeric mixture for xanthine ( X ), one of intermediates of nucleic acids degradation, have been investigated for the first time. Fifteen NH and twenty-eight CH tautomers, including rotamers of OH groups, have been considered to select the most potential ones for one-electron oxidation ( X → X + + e) and one-electron reduction ( X + e → X − ). For selected isomers, thermochemistry of prototropy and redox processes have been studied at the DFT(B3LYP)/6–311+G(d,p) level. The DFT calculations provide a new important information on isomeric composition of redox forms ( X + and X − ) and also on ionization processes for X in vacuo . Positive ionization favors the dioxo NH tautomer – the main form for X , but also, it increases the stability of one hydroxy-oxo isomer – neglected for X . Although the CH tautomers can be neglected for both X and X + , some of them have very low energies for X − and dramatically change tautomeric preferences. They seem to dictate thermochemistry of negative ionization. Variations of bonds lengths for selected neutral and ionized xanthine-isomers have been examined at the DFT level by employing the geometry-based HOMED (Harmonic Oscillator Model of Electron Delocalization) descriptor, recently extended for heterocompounds. The HOMED indices seem to be parallel to the relative Gibbs energies only for the dioxo NH and CH isomers. For the mono- and di-hydroxy forms, scatter plots exist." @default.
• W4224277105 created "2022-04-26" @default.
• W4224277105 creator A5003180390 @default.
• W4224277105 creator A5077373114 @default.
• W4224277105 date "2022-08-01" @default.
• W4224277105 modified "2023-10-13" @default.
• W4224277105 title "Structural and thermochemical consequences of prototropy and ionization for the biomolecule xanthine in vacuo" @default.
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