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Universal Trends between Acid Dissociation Constants in Protic and Aprotic Solvents

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en
dc.contributor.author Busch, Michael
dc.contributor.author Ahlberg, Elisabet
dc.contributor.author Laasonen, Kari
dc.date.accessioned 2022-11-09T08:03:09Z
dc.date.available 2022-11-09T08:03:09Z
dc.date.issued 2022-10-21
dc.identifier.citation Busch , 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.202201667 en
dc.identifier.issn 0947-6539
dc.identifier.issn 1521-3765
dc.identifier.other PURE UUID: ac547683-da09-4760-8b6f-243fa339ca68
dc.identifier.other PURE ITEMURL: https://research.aalto.fi/en/publications/ac547683-da09-4760-8b6f-243fa339ca68
dc.identifier.other PURE LINK: http://www.scopus.com/inward/record.url?scp=85137037816&partnerID=8YFLogxK
dc.identifier.other PURE FILEURL: https://research.aalto.fi/files/91142710/Universal_Trends_between_Acid_Dissociation_Constants_in_Protic_and_Aprotic_Solvents.pdf
dc.identifier.uri https://aaltodoc.aalto.fi/handle/123456789/117688
dc.description Funding 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.abstract pKa 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.format.extent 12
dc.format.mimetype application/pdf
dc.language.iso en en
dc.publisher WILEY-VCH VERLAG
dc.relation.ispartofseries Chemistry - A European Journal en
dc.relation.ispartofseries Volume 28, issue 59 en
dc.rights openAccess en
dc.title Universal Trends between Acid Dissociation Constants in Protic and Aprotic Solvents en
dc.type A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä fi
dc.description.version Peer reviewed en
dc.contributor.department Department of Chemistry and Materials Science
dc.contributor.department University of Gothenburg
dc.subject.keyword DFT
dc.subject.keyword diazepam
dc.subject.keyword ibuprofen
dc.subject.keyword morphine
dc.subject.keyword non-aqueous solvents
dc.subject.keyword pharmacology
dc.subject.keyword pKa
dc.identifier.urn URN:NBN:fi:aalto-202211096459
dc.identifier.doi 10.1002/chem.202201667
dc.type.version publishedVersion

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