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Solubility

Unsure why sodium benzoate is more soluble in water than phenylamine?
The benzene ring in phenylamine is electron withdrawing and so the lone pair on the nitrogen atom is much less 'partially' negative than it would normally be and so the bond strength and hence the solubility is much lower than it would be if say you removed the benzene ring. On the other hand sodium benzoate is ionic and so can be split into separate ions in solution with a more exothermic result and so a greater solubility. Hope that helps

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