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@article{a075e6957bb943f19cc01c918e6189c9,
title = "Predictions of flavonoid solubility in ionic liquids by COSMO-RS: experimental verification, structural elucidation, and solvation characterization",
publisher = "Royal Society of Chemistry",
author = "Zheng Guo and Bena-Marie Lue and Kaj Thomsen and Meyer, {Anne S.} and Xuebing Xu",
year = "2007",
doi = "10.1039/b709786g",
volume = "9",
number = "12",
pages = "1362--1373",
journal = "Green Chemistry",
issn = "1463-9262",

}

RIS

TY - JOUR

T1 - Predictions of flavonoid solubility in ionic liquids by COSMO-RS: experimental verification, structural elucidation, and solvation characterization

A1 - Guo,Zheng

A1 - Lue,Bena-Marie

A1 - Thomsen,Kaj

A1 - Meyer,Anne S.

A1 - Xu,Xuebing

AU - Guo,Zheng

AU - Lue,Bena-Marie

AU - Thomsen,Kaj

AU - Meyer,Anne S.

AU - Xu,Xuebing

PB - Royal Society of Chemistry

PY - 2007

Y1 - 2007

N2 - Predictions of the solubility of flavonoids in a large variety of ionic liquids (ILs) with over 1800 available structures were examined based on COSMO-RS computation. The results show that the solubilities of flavonoids are strongly anion-dependent. Experimental measurement of the solubilities of esculin and rutin in 12 ILs with varying anions and cations show that predicted and experimental results generally have a good agreement. Based on the sound physical basis of COSMO-RS, the solubility changes of flavonoids were quantitatively associated with solvation interactions and structural characteristics of ILs. COSMO-RS derived parameters, i.e. misfit, H-bonding and van der Waals interaction energy, are shown to be capable of characterizing the complicated multiple interactions in the IL system effectively. H-bonding interaction is the most dominant interaction for ILs (followed by misfit and van der Waals interactions) to determine the solubility of flavonoids, and the anionic part has greater effect on the overall H-bonding capability of the IL. Based on basicity of anions, ILs were categorized into 3 groups, corresponding to the classification of the solubility of flavonoid. COSMO sigma-moment descriptors, which roughly denote the characteristic properties of the ILs, might be of general value to have a fast estimation for the solubilities of flavonoids as well as those compounds with massive moieties as H-bonding donors. The results obtained in this work may be important for achieving an improved understanding of IL solvations and the tailoring of the desired structures of ILs used as the media for efficient enzymatic esterification of flavonoids.

AB - Predictions of the solubility of flavonoids in a large variety of ionic liquids (ILs) with over 1800 available structures were examined based on COSMO-RS computation. The results show that the solubilities of flavonoids are strongly anion-dependent. Experimental measurement of the solubilities of esculin and rutin in 12 ILs with varying anions and cations show that predicted and experimental results generally have a good agreement. Based on the sound physical basis of COSMO-RS, the solubility changes of flavonoids were quantitatively associated with solvation interactions and structural characteristics of ILs. COSMO-RS derived parameters, i.e. misfit, H-bonding and van der Waals interaction energy, are shown to be capable of characterizing the complicated multiple interactions in the IL system effectively. H-bonding interaction is the most dominant interaction for ILs (followed by misfit and van der Waals interactions) to determine the solubility of flavonoids, and the anionic part has greater effect on the overall H-bonding capability of the IL. Based on basicity of anions, ILs were categorized into 3 groups, corresponding to the classification of the solubility of flavonoid. COSMO sigma-moment descriptors, which roughly denote the characteristic properties of the ILs, might be of general value to have a fast estimation for the solubilities of flavonoids as well as those compounds with massive moieties as H-bonding donors. The results obtained in this work may be important for achieving an improved understanding of IL solvations and the tailoring of the desired structures of ILs used as the media for efficient enzymatic esterification of flavonoids.

UR - http://www.rsc.org/Publishing/Journals/gc/Index.asp

U2 - 10.1039/b709786g

DO - 10.1039/b709786g

JO - Green Chemistry

JF - Green Chemistry

SN - 1463-9262

IS - 12

VL - 9

SP - 1362

EP - 1373

ER -