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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: AhmedEzatAlzawalaty on March 15, 2007, 07:24:39 PM

Title: Ampicillin
Post by: AhmedEzatAlzawalaty on March 15, 2007, 07:24:39 PM

Why ampicillin is acid resistant

Title: Re: Ampicillin
Post by: RaZ on March 15, 2007, 08:25:18 PM

It's because the amine group (next to the phenyl) is an EWG.  This stops the oxygen from the carbonyl of the amide attacking the carbonyl on the B-lactam ring and opening it up.  Hope that helps.

Title: Re: Ampicillin
Post by: EtOH on March 20, 2007, 07:12:24 PM

Since when is amine an EWG? It's a strong activator which means it would stabilize by donating to the ring...