acid/base; mechanism of phenytoin?

StudentinaByStudentina

Hello everyone, I don't understand why intramolecular proton transfer is taking place here?

Why doesn't the negative charge simply remain on the first nitrogen atom and then react with H2O? The same product would result.

Does the stability of the negative charge have anything to do with it?

Thank you in advance!! :)) I am grateful for any approach

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ZitrusLiebe
ZitrusLiebe
2 years ago

Imides are very strong acids (phthalimide pKs of 8), amide and urea N's are >20. The GGW becomes more important in other reactions or ring openings. It doesn't matter because only protons react.

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Spikeman197
Spikeman197
2 years ago

I don't see it as dogmatic/ultimate. The first figure shows 'only' that C is in the GGW with the other shape, C even having to be more stable.

A 2nd GGW is added in aqueous solution, this being determined primarily on the right side. The first GGW no longer plays a role.

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Studentina
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Studentina
2 years ago
Reply to  Spikeman197

And would the first (with the negative charge at the upper N atom) also lead to the same product with H2O or would it not be possible?

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Spikeman197
Spikeman197
2 years ago
Reply to  Studentina

Sure, it would come out exactly the same.

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