In this question, it is explained how basicity and nucleophilicity are different and how the solvent used affects nuclephilicity.

What I wondered was whether there would be a difference in the basic strength of say $\ce{Cl-}$ in $\ce{H2O}$ (a protic solvent) and $\ce{DMSO}$ (an aprotic solvent).

My answer would be that due to solvation in $\ce{H2O}$, the $\ce{Cl-}$ ions would get stabilised and hence their basic strength would reduce as compared to those ions which are dissolved in $\ce{DMSO}$.

Am I right in saying this or did I overlook something?

  • $\begingroup$ I think you could more explicit by considering the differential stabilization of the species (i.e., $\ce{H2O}$ and $\ce{Cl-}$ versus $\ce{OH-}$ and $\ce{HCl}$ for a better answer. $\endgroup$
    – Zhe
    Apr 29, 2022 at 17:02
  • $\begingroup$ Hey I'm sorry but I don't really understand what you're trying to say, could you rephrase that somehow? $\endgroup$
    – Anili
    Apr 29, 2022 at 17:05
  • 1
    $\begingroup$ The basicity you're talking about is thermodynamic, so you should look at the products versus reactants for the acid-base reaction. You can't just say, oh the of the reactants (the base) is stabilized more than the other, because the product (conjugate acid) could be equally stablized. $\endgroup$
    – Zhe
    Apr 29, 2022 at 17:40
  • $\begingroup$ Ok thanks a lot for explaining @Zhe $\endgroup$
    – Anili
    Apr 30, 2022 at 4:48
  • $\begingroup$ Solvents like DMSO or DMF because of the exposed oxygen supposedly solvate cations more efficiently than anions. Bases such as tertiary butoxide are more reactive in DMSO solutions. Solubility is a concern for a simple ionic such as NaCl. You might research the effect of DMSO on reactions with LiCl or anhydrous HCl or salts that might be more soluble such as tetramethylammonium chloride. $\endgroup$
    – jimchmst
    May 1, 2022 at 3:13


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