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According to me, N,N,2,6-tetramethylaniline should be more basic than N,N,2-trimethylaniline due to more steric inhibition to resonance, but the answer is given opposite. What is the reason for that?

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  • $\begingroup$ It increases basicity as well as acidity.That's the reason why 2-methyl-n,n-dimethylaniline is more basic than aniline $\endgroup$ Aug 18 '20 at 10:27
  • $\begingroup$ @Safdar SIR = Steric inhibition of resonance decreases lone-pair delocalization and should thereby increase basicity, but the opposite is happening here. $\endgroup$ Aug 18 '20 at 12:41
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    $\begingroup$ The lack of solvation might be a valid reason since both show SIR. the more number of steric groups, the harder it is to solvate.[chemistry.stackexchange.com/a/8636/95133 ] $\endgroup$ Aug 18 '20 at 14:38
  • $\begingroup$ @Dylan Rodrigues: "It [SIR?[ increases basicity as well as the acidity...of the conjugate acid." $\endgroup$
    – user55119
    Aug 18 '20 at 17:11
  • $\begingroup$ Steric inhibition of protonation is crucial here. $\endgroup$
    – Mithoron
    Aug 18 '20 at 19:37

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