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Question

When the imidazole ring of Histidine is protonated, tendency of nitrogen to be protonated (proton migrates from COOH) is in the order?
938859_b253fa131ab14e3d92556db7323281cf.png

A
β > γ > α
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B
γ > β > α
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C
γ > α > β
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D
β > α > γ
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Solution

The correct option is C γ > α > β
γ(NH2) is close to -COOH, in β(NH), the lone pair of electrons is involved in resonance, and the lone pair on α(N=) is intact on Natom.
The order is :
γ > α > β

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