Why does direct nitration of aniline yield a significant amount (47%) of the meta-nitro derivative, despite $$-NH_2$$ being an ortho-para director?

Question

Why does direct nitration of aniline yield a significant amount (47%) of the meta-nitro derivative, despite  $$-NH_2$$   being an ortho-para director?

Canvas Classes · Accepted Answer

In the strongly acidic medium used for nitration, aniline is protonated to form the anilinium ion ( $$Ph-NH_3^+$$  ). This ion is electron-withdrawing and meta-directing

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