Universal trends between acid dissociation constants in protic and aprotic solvents

peer-reviewed
Erstveröffentlichung
2022-08-25Autoren
Busch, Michael
Ahlberg, Elisabet
Laasonen, Kari
Wissenschaftlicher Artikel
Erschienen in
Chemistry – A European Journal ; 28 (2022), 59. - Art.-Nr. e202201667. - ISSN 0947-6539. - eISSN 1521-3765
Link zur Originalveröffentlichung
https://dx.doi.org/10.1002/chem.202201667Fakultäten
Fakultät für NaturwissenschaftenInstitutionen
Institut für Theoretische ChemieDokumentversion
Veröffentlichte Version (Verlags-PDF)Zusammenfassung
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.
Schlagwörter
[GND]: Nichtwässriges Lösungsmittel | Pharmakologie | Morphin[LCSH]: Pharmacology | Morphine | Diazepam | Ibuprofen
[Freie Schlagwörter]: pKa | non-aqueous solvents | DFT
[DDC Sachgruppe]: DDC 540 / Chemistry & allied sciences
Metadata
Zur LanganzeigeDOI & Zitiervorlage
Nutzen Sie bitte diesen Identifier für Zitate & Links: http://dx.doi.org/10.18725/OPARU-47933
Busch, Michael; Ahlberg, Elisabet; Laasonen, Kari (2023): Universal trends between acid dissociation constants in protic and aprotic solvents. Open Access Repositorium der Universität Ulm und Technischen Hochschule Ulm. http://dx.doi.org/10.18725/OPARU-47933
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