Comparison of the acidic nature between substituted benzoic acids and acetic acid

[*p*-Methoxybenzoic acid](https://en.wikipedia.org/wiki/P-Anisic_acid) $(\mathrm{p}K\_\mathrm{a} = 4.47)$ is a stronger acid than [acetic acid](https://en.wikipedia.org/wiki/Acetic_acid) $(\mathrm{p}K\_\mathrm{a} = 4.76)$ despite the presence of an electron donating group. I understand this is due to the greater electronegativity of $\mathrm{sp^2}$ carbon to which the carboxyl carbon is attached.


But is there a substituent with strong enough donating nature to make [benzoic acid](https://en.wikipedia.org/wiki/Benzoic_acid) $(\mathrm{p}K\_\mathrm{a} = 4.20)$ less acidic than acetic acid? If there are, which one might be just strong enough?





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> But is there a substituent with strong enough donating nature to make benzoic acid less acidic than acetic acid?
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Yes, we can make benzoic acid less acidic than acetic acid by simply substituting strong electron donating groups like $\ce{-N(CH3)2}$ to the para position of benzoic acid. By substituting $\ce{-N(CH3)2}$ to the para position of benzoic acid we can reduce it's [$\mathrm{p}K\_\mathrm{a}$ to $6.03$](https://www.drugfuture.com/chemdata/4-Dimethylamino-benzoic-Acid.html#:%7E:text=pKa%206.027%3B%20pKb%2011.488.)! Which is much less acidic than acetic acid.


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