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According to me, acidity for these two compounds depends primarily upon two factors:

  • inductive effect due to the ring

  • electronegativity of the atom bearing the hydrogen atom

If the first factor predominates, second compound would be the most acidic otherwise the first compound would be the most acidic(as nitrogen bears a methyl group too). So, which one is the most acidic?

  • 3
    $\begingroup$ You can also consider this question from the other direction. Which of these conjugate bases is more basic? $\endgroup$ – Zhe Jun 13 '17 at 21:16
  • $\begingroup$ You can also look up the pKa values first, and then choose an explanation that fits the empirical data. $\endgroup$ – Karsten Theis Dec 30 '20 at 15:05

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