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Molecular dynamics study of racemic mixtures. II. Temperature dependence of the separation of ibuprofen racemic mixture with ß-cyclodextrin in methanol solvent
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SYSNO ASEP 0521307 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Molecular dynamics study of racemic mixtures. II. Temperature dependence of the separation of ibuprofen racemic mixture with ß-cyclodextrin in methanol solvent Author(s) Škvára, J. (CZ)
Nezbeda, I. (CZ)
Izák, Pavel (UCHP-M) RID, ORCID, SAIArticle number 112575 Source Title Journal of Molecular Liquids. - : Elsevier - ISSN 0167-7322
Roč. 302, 15 March (2020)Number of pages 6 s. Language eng - English Country NL - Netherlands Keywords racemic mixtures ; ibuprofen and ß-cyclodextrin ; inclusion complex Subject RIV CI - Industrial Chemistry, Chemical Engineering OECD category Chemical process engineering R&D Projects GA17-00089S GA ČR - Czech Science Foundation (CSF) Method of publishing Limited access Institutional support UCHP-M - RVO:67985858 UT WOS 000518870300083 EID SCOPUS 85078854256 DOI 10.1016/j.molliq.2020.112575 Annotation Using a realistic united atom interaction model, molecular dynamics simulations were carried out to investigate properties of mixtures of ibuprofen and ß-cyclodextrin both in vacuo and in solution with methanol solvent. The property in focus here is the temperature dependence of the intermolecular interaction energy and the distribution of hydrogen bonds in inclusion complexes established by both the (R)- and (S)-forms of ibuprofen with ß-cyclodextrin. Temperatures were considered in the range from 260 K to 380 K with an increment of 10 K. It was found that (R)-ibuprofen is strongly bonded inside the cyclodextrin molecule, which is more pronounced in the case when the so-called DOWN complex is formed. However,this effect is diminished in the presence of methanol because methanol molecules tend to occupy the majority of possible hydrogen bonding sites. The temperature dependence is not monotonic, and for the DOWN complex in methanol it exhibits two maxima, at 260 K and 310 K. For the UP complex no significant difference was observed at any temperature within the considered range. These results may help both experimentalists and theorists to understand the process of chiral selection of ibuprofen enantiomers. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2021 Electronic address http://hdl.handle.net/11104/0306396
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