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The basicity order of aniline and 2,6-tertiary butyl aniline is the latter greater than the former. Why does the ortho effect not make it the other way around? Or am I missing something?enter image description here

Atharva
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    Is your first sentence a statement or a question? Providing pKb's would be helpful. – user55119 Jan 23 '20 at 16:51
  • First thing to correct is that ortho effect is applicable only when u have -COOH..ie..comparing acidity or stuff for substituted benzoic acid. – Muskaan Jan 23 '20 at 16:52
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    Here u have to consider SIP effect .... – Muskaan Jan 23 '20 at 16:54
  • I don't know where to find pKbs, sorry :( – Atharva Jan 23 '20 at 17:09
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    Ortho effect is present in anilines too – Atharva Jan 23 '20 at 17:09
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    https://chemistry.stackexchange.com/questions/15412/why-can-the-lone-pair-not-align-with-the-phenyl-moiety-in-2-6-xylidine https://chemistry.stackexchange.com/questions/7683/ortho-effect-in-substituted-aromatic-acids-and-bases – Mithoron Jan 23 '20 at 18:16
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    https://chemistry.stackexchange.com/questions/14767/steric-hindrance-and-br%c3%b8nsted-basicity https://chemistry.stackexchange.com/questions/87461/is-steric-inhibition-of-resonance-or-steric-inhibition-of-protonation-dominant-i – Mithoron Jan 23 '20 at 18:23
  • Thank you! I don't understand all of the answers very much, but I think I caught the gist of it. Does it mean that m-xylene with NH2 meta to both is less basic that with the NH2 between the CH3's? Even with the double ortho effect? – Atharva Jan 24 '20 at 13:57

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