Universal Trends between Acid Dissociation Constants in Protic and Aprotic Solvents

Michael Busch*, Elisabet Ahlberg, Kari Laasonen

*Tämän työn vastaava kirjoittaja

Tutkimustuotos: LehtiartikkeliArticleScientificvertaisarvioitu

6 Sitaatiot (Scopus)
36 Lataukset (Pure)

Abstrakti

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.

AlkuperäiskieliEnglanti
Artikkelie202201667
Sivumäärä12
JulkaisuChemistry: A European Journal
Vuosikerta28
Numero59
Varhainen verkossa julkaisun päivämäärä25 elok. 2022
DOI - pysyväislinkit
TilaJulkaistu - 21 lokak. 2022
OKM-julkaisutyyppiA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

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