Studies on the hydrogen bond acidity, and other descriptors and properties for hydroxyflavones and hydroxyisoflavones

Abraham, Michael H.; Acree, William E.; Earp, Cody E.; Vladimirova, Anna; Whaley, William L.

doi:10.1016/j.molliq.2015.05.011

Cited by 23 publications

(11 citation statements)

References 35 publications

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“…Excepting two solvents (1,3-propanediol and 1,3-butanediol), the Abraham descriptors of the solvents studied in this work are available in recent literature [37,53,54]. Therefore, using a given set of solubility data in solvents with high chemical diversity, the solute's coefficients can be estimated by multiple linear regression analysis.…”

Section: The Abraham Solvation Modelmentioning

confidence: 99%

Solvent and temperature effects on the solubility of syringic, vanillic or veratric acids: Experimental, modeling and solid phase studies

Vilas-Boas

Vieira

Brandão

et al. 2019

Journal of Molecular Liquids

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The solubility of syringic acid, vanillic acid and veratric acid was measured in pure water and eleven organic solvents (methanol, ethanol, 1-propanol, 2-propanol, 2-butanone, ethyl acetate, acetonitrile, dimethylformamide, 1,2-propanediol, 1,3-propanediol and 1,3-butanediol), at 298.2 K and 313.2 K. Besides the solubility data, the melting temperatures and enthalpies of the solutes were determined by differential scanning calorimetry, while powder and single X-ray diffraction were used to resolve the solute solid structure, before and after the solubility studies. For modeling purposes, the NRTL-SAC model, also combined with the Reference Solvent Approach (RSA), and the Abraham solvation model were applied to describe the solid-liquid equilibria of the binary systems. A set of solvents was used to estimate the model parameters and afterwards, solubility predictions were carried out for binary systems not included in the correlation step. Better results were obtained using the Abraham solvation model with average relative deviations (ARD) of 15% for the correlation set and 26% for the predictions, which are more satisfactory than the results found with the NRTL-SAC model (33% for the correlation and 59% for the predictions) or the NRTL-SAC model combined with RSA (30% for the correlation and 59% for the predictions).

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Section: The Abraham Solvation Modelmentioning

confidence: 99%

Solvent and temperature effects on the solubility of syringic, vanillic or veratric acids: Experimental, modeling and solid phase studies

Vilas-Boas

Vieira

Brandão

et al. 2019

Journal of Molecular Liquids

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“…The central importance of HBs in materials design and fundamental chemistry has motivated development of classical electrostatic models 27,[49][50] and empirical correlations [50][51][52] , and first-principles computational modeling is crucial to the continued development of understanding hydrogen bonding [53][54][55] . In response to recent experimental and theoretical advances, the DFT-based computational screening has become an increasingly valuable tool for the design and discovery of new materials [66][67][68][69][70][71] thanks both to recent improvements in computational efficiency and accuracy (e.g., in descriptions of intermolecular forces through direct treatment of dispersion [72][73].…”

Section: Introductionmentioning

confidence: 99%

Computational Discovery of Hydrogen Bond Design Rules for Electrochemical Ion Separation

2016

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Selective ion separation is a major challenge with far-ranging impact from water desalination to product separation in catalysis. Recently introduced ferrocenium(Fc + )/ferrocene(Fc) polymer electrode materials have been demonstrated experimentally and theoretically to selectively bind carboxylates over perchlorate through weak C-H … O hydrogen bond (HB) interactions that favor carboxylates, despite the comparable size and charge of the two species. However, practical application of this technology in aqueous environments requires further selectivity enhancement. Using a first-principles discovery approach, we investigate the effect of Fc/Fc + functional groups (FGs) on the selectivity and reversibility of formate-Fc + adsorption with respect to perchlorate in aqueous solution. Our wide design space of 44 FGs enables identification of FGs with higher selectivity and rationalization of trends through electronic energy decomposition analysis or geometric hydrogen bonding analysis. Overall, we observe weaker, longer HBs for perchlorate as compared to formate with Fc + . We further identify Fc + functionalizations that simultaneously increase selectivity for formate in aqueous environments but permit rapid release from neutral Fc. We introduce the materiaphore, a 3D abstraction of these design rules, to help guide nextgeneration material optimization for selective ion sorption. This approach is expected to have broad relevance in computational discovery for molecular recognition, sensing, separations, and catalysis.2

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“…The values of log Kp of the 247 compounds or species in our data set covers both 'highly permeable' and 'poorly permeable' values, varying from -10.01 to -3.00, and meets a normal distribution very well, with a mean of -6.027 and a standard deviation of 1.165, as seen in Figure 1. Stephens et al (2012) and Zhang et al (2012) or obtained as described before (Abraham et al, 2015a;Abraham et al, 2015b;Clarke and Mallon, 2012); ionic descriptors obtained as described before (Abraham and Acree, 2016). b Cited studies where log Kp (obs) was obtained.…”

Section: Resultsmentioning

confidence: 99%

An equation for the prediction of human skin permeability of neutral molecules, ions and ionic species

Zhang

Abraham

Liu

2017

International Journal of Pharmaceutics

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Accepted ManuscriptThis is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

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Studies on the hydrogen bond acidity, and other descriptors and properties for hydroxyflavones and hydroxyisoflavones

Cited by 23 publications

References 35 publications

Solvent and temperature effects on the solubility of syringic, vanillic or veratric acids: Experimental, modeling and solid phase studies

Solvent and temperature effects on the solubility of syringic, vanillic or veratric acids: Experimental, modeling and solid phase studies

Computational Discovery of Hydrogen Bond Design Rules for Electrochemical Ion Separation

An equation for the prediction of human skin permeability of neutral molecules, ions and ionic species

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