I have analyzed an IR spectrum and found out that my compound (o-nitrobenzoic acid) has a nitro group, carboxylic group, and benzene ring.

I was curious to know: if regioselectivity effects the solubility of the compound? If/If not regioselectivity effects the solubility of o-nitrobenzoic acid, what would be the best solubility test to run for o-nitrobenzoic acid since it has a carboxylic acid and a nitro group in the ortho-position? And, if I wanted to test o-nitrobenzoic acid functional groups, what would be some good classification tests to run?

  • $\begingroup$ Of course the structure of a molecule affects solubility, but solubility isn't a particularly specific test. Old fashion organic qualitative analysis has all sorts of tests for different functional groups. There is also melting point/boiling point for isomers. MPs - 2-Nitrobenzoic acid 147.5 °C; 3-Nitrobenzoic acid 139 to 141 °C; 4-Nitrobenzoic acid 237 °C $\endgroup$
    – MaxW
    Apr 1, 2020 at 5:46
  • $\begingroup$ All substituted benzoic acids are easily soluble in NaOH solutions. Your acid can be esterified and give perfumes. It also may be reduced by iron in acidic solution to produce o-aminobenzoic acid $\endgroup$
    – Maurice
    Apr 1, 2020 at 19:25


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