Can nitric acid be protonated?

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Can nitric acid be protonated?

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Answer 1 · 2016-09-08T16:05:58

In highly acidic media, nitric acid can be protonated.

Explanation:

This is the basis for the nitrating mixture used to prepare nitro-arenes:

$H_{2} S O_{4} (a q) + H N O_{3} (a q) \to H S O_{4}^{-} + H_{2} N O_{3}^{+}$ $H_2SO_4(aq) + HNO_3(aq) rarr HSO_4^(-) +H_2NO_3^+$

$H_{2} N O_{3}^{+} \to N O_{2}^{+} + H_{2} O$ $H_2NO_3^+ rarr NO_2^+ + H_2O$

The nitronium ion is a very potent electrophile because of the quaternized nitrogen centre in $O = N^{+} = O$ $O=N^+=O$ . As to how to quantify this basicity, you have got me. We use a highly electrophilc (i.e. acidic) medium to produce the nitronium ion.

The nitronium ion is produced by these means in explosives manufacture when toluene is nitrated, to produce $trinitrotoluene$ $"trinitrotoluene"$ . I have no doubt it is safe but it is something I would not like to do.

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Can nitric acid be protonated?

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