How is NH in thymine amphiprotic?

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Sara Sadrolsadat 1G
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How is NH in thymine amphiprotic?

Postby Sara Sadrolsadat 1G » Sat Dec 08, 2018 2:52 pm

In question 12.127 in the 6th edition, it is determined that the 2 NHs in thymine are amphiprotic because they can gain or give a proton. But why would NH lose an H if it would give N a negative charge?

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Re: How is NH in thymine amphiprotic?

Postby Chem_Mod » Sun Dec 09, 2018 12:59 pm

Sometimes nitrogens are still willing to give up protons if they have a way of stabilizing the resulting negative charge. Thymine's structure lends it the ability to balance the charge by resonance, whether the charge is positive or negative, so it is find either accepting or giving a proton.

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