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Universal Trends between Acid Dissociation Constants in Protic and Aprotic Solvents

Authors: Ahlberg, Elisabet; Laasonen; Kari; Busch, Michael;

Universal Trends between Acid Dissociation Constants in Protic and Aprotic Solvents

Abstract

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.

Countries
Germany, Finland
Keywords

Pharmacology, Ions, Pharmakologie, Diazepam, Morphine, info:eu-repo/classification/ddc/540, non-aqueous solvents, Ibuprofen, morphine, DFT, Nichtwässriges Lösungsmittel, Morphin, Ammonium Compounds, Solvents, pKa, pharmacology, ta116, Research Articles, diazepam, ibuprofen

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    influence
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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
8
Top 10%
Average
Top 10%
Green
hybrid