2017
DOI: 10.1021/acs.jpca.7b09330
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Theoretical Models for Quantitative Description of the Acid–Base Equilibria of the 5,6-Substituted Uracils

Abstract: The acidities of 18 5,6-substituted uracils have been numerically estimated as pK values in terms of three theoretical models. The first scheme includes the calculation of the gas-phase acidity of uracil with the G3MP2B3 method and taking into account the solvent effect using the polarizable continuum approximation PCM(SMD)-TPSS/aug-cc-pVTZ. The second model is one step and implies calculation of the free Gibbs energies of the hydrate complex of uracil (and its anion) with 5 water molecules by the TPSS/aug-cc-… Show more

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Cited by 7 publications
(1 citation statement)
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“…However, a systematic acidity scale for these CILs is highly valuable to access the stability of ILs as well as catalytic ability of organocatalysts. There have been many works focused on estimating the acidities of small organic acids and bases by theoretical methods in the past few years. Therefore, alternatively, we employ a sophisticated theoretical calculation, which is calibrated by the experimental results, to establish a comprehensive acidity scale for a variety of CILs, including phosphonium, ammonium, imidazolium, pyridinium, pyrrolidinium, piperidinium, morpholinium, guanadinium, and amidinium cations in DMSO. The calculated acidities for different classes of CILs were compared with each other and also with the precursor acidities of several weak organic anions and some superbases.…”
Section: Introductionmentioning
confidence: 99%
“…However, a systematic acidity scale for these CILs is highly valuable to access the stability of ILs as well as catalytic ability of organocatalysts. There have been many works focused on estimating the acidities of small organic acids and bases by theoretical methods in the past few years. Therefore, alternatively, we employ a sophisticated theoretical calculation, which is calibrated by the experimental results, to establish a comprehensive acidity scale for a variety of CILs, including phosphonium, ammonium, imidazolium, pyridinium, pyrrolidinium, piperidinium, morpholinium, guanadinium, and amidinium cations in DMSO. The calculated acidities for different classes of CILs were compared with each other and also with the precursor acidities of several weak organic anions and some superbases.…”
Section: Introductionmentioning
confidence: 99%