0
$\begingroup$

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?

$\endgroup$
5
  • $\begingroup$ 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

0

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Browse other questions tagged or ask your own question.