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Why does attaching an $\ce{-NO2}$ group at the ortho position of benzoic acid cause $\ce{-COOH}$ to become perpendicular to the plane of the benzene ring? Why doesn't the nitro group get pushed out while $\ce{-COOH}$ stays on the plane?

Also, in the case of two $\ce{-NO2}$ groups attached on the ortho and meta positions of benzoic acid, both the nitro groups become perpendicular to the benzene ring while $\ce{-COOH}$ remains at an angle to the plane. Why doesn't it become perpendicular this time?

Here is what I referred to for the structure of 2-nitrobenzoic acid :https://pubchem.ncbi.nlm.nih.gov/compound/2-Nitrobenzoic-acid#section=3D-Conformer&fullscreen=true

Here is what I referred to for the structure of 2,3-dinitrobenzoic acid :https://pubchem.ncbi.nlm.nih.gov/compound/2,3-diNitrobenzoic-acid#section=3D-Conformer&fullscreen=true

If you feel these structures arent correct please do give a reference to where I can find the right structure. :)

Grace Matson
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    It's quite not how you say. – Mithoron Mar 03 '20 at 16:38
  • Then what is it like? Could you explain...? Im pretty confused – Grace Matson Mar 04 '20 at 11:46
  • https://chemistry.stackexchange.com/questions/7683/ortho-effect-in-substituted-aromatic-acids-and-bases – Mithoron Mar 04 '20 at 17:30
  • That thread is specifically about the consequences of SIR and SIP... I already know about that. It was after learning that when I looked up the 3D structure of o-nitrobenzoic acid and got the doubt... I just want to know why -COOH rotates instead of -NO2 which stays perfectly planar... I want the reason behind the phenomenon not the consequence. – Grace Matson Mar 05 '20 at 02:10
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    Structure of o-nitrobenzoic acid. Check out the 3D conformer given in this link :https://www.google.com/url?sa=t&source=web&rct=j&url=https://pubchem.ncbi.nlm.nih.gov/compound/2-Nitrobenzoic-acid&ved=2ahUKEwi454XKoILoAhUIfH0KHV3vAEEQFjACegQIBhAB&usg=AOvVaw3JvBtRwipcskI1y9JGj49F – Grace Matson Mar 05 '20 at 02:11
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    Better question is if you can really trust Puchem. – Mithoron Mar 05 '20 at 02:17

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