Universal Trends between Acid Dissociation Constants in Protic and Aprotic Solvents

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dc.contributorAalto-yliopistofi
dc.contributorAalto Universityen
dc.contributor.authorBusch, Michaelen_US
dc.contributor.authorAhlberg, Elisabeten_US
dc.contributor.authorLaasonen, Karien_US
dc.contributor.departmentDepartment of Chemistry and Materials Scienceen
dc.contributor.groupauthorComputational Chemistryen
dc.contributor.organizationUniversity of Gothenburgen_US
dc.date.accessioned2022-11-09T08:03:09Z
dc.date.available2022-11-09T08:03:09Z
dc.date.issued2022-10-21en_US
dc.descriptionFunding Information: Calculations were performed at the Chalmers Centre for Computational Science and Engineering (C3SE) and the Finnish IT centre for science (CSC). M.B. and K.L. acknowledge financial support from the Jane and Aatos Erkko Foundation through the “Renewable energy storage to high value chemicals” project. M.B. also acknowledges support from the Dr. Barbara‐Mez‐Starck foundation. Open Access funding enabled and organized by Projekt DEAL. Publisher Copyright: © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
dc.description.abstractpKa values in non-aqueous solvents are of critical importance in many areas of chemistry. Our knowledge is, despite their relevance, still limited to the most fundamental properties and few pKa values in the most common solvents. Taking advantage of a recently introduced computationally efficient procedure we computed the pKa values of 182 compounds in 21 solvents. This data set is used to establish for the first time universal trends between all solvents. Our computations indicate, that the total charge of the molecule and the charge of the acidic group combined with the Kamlet-Taft solvatochromic parameters are sufficient to predict pKa values with at least semi- quantitative accuracy. We find, that neutral acids such as alcohols are strongly affected by the solvent properties. This is contrasted by cationic acids like ammonium ions whose pKa is often almost completely independent from the choice of solvent.en
dc.description.versionPeer revieweden
dc.format.extent12
dc.format.mimetypeapplication/pdfen_US
dc.identifier.citationBusch, M, Ahlberg, E & Laasonen, K 2022, ' Universal Trends between Acid Dissociation Constants in Protic and Aprotic Solvents ', Chemistry: A European Journal, vol. 28, no. 59, e202201667 . https://doi.org/10.1002/chem.202201667en
dc.identifier.doi10.1002/chem.202201667en_US
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.otherPURE UUID: ac547683-da09-4760-8b6f-243fa339ca68en_US
dc.identifier.otherPURE ITEMURL: https://research.aalto.fi/en/publications/ac547683-da09-4760-8b6f-243fa339ca68en_US
dc.identifier.otherPURE LINK: http://www.scopus.com/inward/record.url?scp=85137037816&partnerID=8YFLogxKen_US
dc.identifier.otherPURE FILEURL: https://research.aalto.fi/files/91142710/Universal_Trends_between_Acid_Dissociation_Constants_in_Protic_and_Aprotic_Solvents.pdfen_US
dc.identifier.urihttps://aaltodoc.aalto.fi/handle/123456789/117688
dc.identifier.urnURN:NBN:fi:aalto-202211096459
dc.language.isoenen
dc.publisherWILEY-VCH VERLAG
dc.relation.ispartofseriesChemistry - A European Journalen
dc.relation.ispartofseriesVolume 28, issue 59en
dc.rightsopenAccessen
dc.subject.keywordDFTen_US
dc.subject.keyworddiazepamen_US
dc.subject.keywordibuprofenen_US
dc.subject.keywordmorphineen_US
dc.subject.keywordnon-aqueous solventsen_US
dc.subject.keywordpharmacologyen_US
dc.subject.keywordpKaen_US
dc.titleUniversal Trends between Acid Dissociation Constants in Protic and Aprotic Solventsen
dc.typeA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessäfi
dc.type.versionpublishedVersion
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