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Mixed Explicit-Implicit Solvation Approach for Modeling of Alkane Complexation in Water-Soluble Self-Assembled Capsules
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-7803-5033
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Number of Authors: 52018 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 39, p. 12527-12537Article in journal (Refereed) Published
Abstract [en]

The host-guest binding properties of a water-soluble resorcinarene-based cavitand are examined using density functional theory methodology. Experimentally, the cavitand has been observed to self-assemble in aqueous solution into both 1:1 and 2:1 host/guest complexes with hydrophobic guests such as n-alkanes. For n-decane, equilibrium was observed between the 1:1 and 2:1 complexes, while 1:1 complexes are formed with shorter n-alkanes and 2:1 complexes are formed with longer ones. These findings are used to assess the standard quantum chemical methodology. It is first shown that a rather advanced com- putational protocol (B3LYP-D3(BJ)/6-311+G(2d,2p) with COSMO-RS and quasi-rigid-rotor-harmonic-oscillator) gives very large errors. Systematic examination of the various elements of the methodology shows that the error stems from the implicit solvation model. A mixed explicit-implicit solvation protocol is developed that involves a parametrization of the hydration free energy of water such that water cluster formation in water is predicted to be thermoneutral. This new approach is demonstrated to lead to a major improvement in the calculated binding free energies of n-alkanes, reproducing very well the 1:1 versus 2:1 host/guest binding trends.

Place, publisher, year, edition, pages
2018. Vol. 140, no 39, p. 12527-12537
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Chemical Sciences
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URN: urn:nbn:se:su:diva-161988DOI: 10.1021/jacs.8b06984ISI: 000446920100035PubMedID: 30185035OAI: oai:DiVA.org:su-161988DiVA, id: diva2:1264495
Available from: 2018-11-20 Created: 2018-11-20 Last updated: 2019-05-07Bibliographically approved

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Daver, HenrikAlgarra, Andrés G.Harvey, Jeremy N.Himo, Fahmi
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