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My argument here is regarding the acidity of o-nitrobenzoic acid being greater than p,m-nitrobenzoic acid. In o-nitrobenzoic acid, there is an intramolecular hydrogen bond which makes the bond stronger and resists the release of H+ ion. Also going by that along with ortho effect in check shouldn't acidity of o-nitrobenzoic acid be relatively lesser? To what extent does hydrogen bonding affect the acidity?

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    $\begingroup$ The intramolecular Hydrogen bonding here is not possible to occur. If you don't see it obviously, I will suggest you to make a $3D$ model to visualise. The hydrogen is far away from the oxygen on the nitro group, as both the group doesn't remain in the same plane. Also, by ortho effect, the acidity doesn't at all become lesser, it is increased for sure. $\endgroup$ – Soumik Das Nov 8 '18 at 13:37
  • $\begingroup$ @Soumik Das. But H can form Hydrogen bond with nitrogen right $\endgroup$ – Equation_Charmer Mar 5 '20 at 12:38
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    $\begingroup$ @dhaneshvijay Not really.. Because for forming Hydrogen bonds, the other atom should be highly electronegative and most importantly rich in electron density. Here the Nitrogen in Nitro group is positively charged, which makes it electron deficienct and not suitable for hydrogen bonding in this case. $\endgroup$ – Soumik Das Mar 6 '20 at 13:09

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