Monday, April 10, 2017

physical chemistry - Which is the strongest base?


When I was in lower grades, I was taught $\ce{NaOH and KOH}$ are the strongest bases. But I realised later that there can be more stronger ones. After a bit of research on the internet, I found these three to be spoken more about.



  1. Lithium diisopropylamide (LDA)

  2. Methyllithium (MeLi)

  3. Butyllithium (BuLi)


Wikipedia on LDA says that the $\mathrm{p}K_\mathrm{a}$ of its conjugate acid is $36$, which means the $\mathrm{p}K_\mathrm{b}$ value at $\pu{298K}$ is $-22$. (Since $\mathrm{p}K_\mathrm{a} + \mathrm{p}K_\mathrm{b} = 14$).
Likewise, for BuLi and MeLi I found the $\mathrm{p}K_\mathrm{b}$ value to be $-36$ and $-34$ respectively from the $\mathrm{p}K_\mathrm{a}$ values of their conjugate acids. So, can we conclude that BuLi is the strongest base? Is this absolute basic strength defined?





Sources for $\mathrm{p}K_\mathrm{a}$ values:





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