Penicillin Structure: Acidic, Neutral or Basic?

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SUMMARY

The discussion centers on the acidity of penicillin, concluding that penicillin is acidic due to the presence of the carboxylic acid group (-COOH). The analysis highlights that the nitrogen atoms in penicillin are bonded to carbonyl groups (=C=O), which reduce their basicity by decreasing electron density. This reasoning is validated by participants in the forum, confirming the acidic nature of penicillin based on its structural components.

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  • Basic principles of acid-base chemistry.
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Homework Statement



"Penicillin"[/URL]

From the structure of penicillin above, would you expect it to be acidic, neutral or basic? Explain your answer as fully as you can.

[h2]Homework Equations[/h2]
[h2]The Attempt at a Solution[/h2]

I think it would be acidic because of the -COOH. The -NH- can be basic, but it is attached to =C=O which is deactivating. the electron density on the N atom is reduced and the tendency to accept a proton decreases.

The other Nitrogen atom is also bonded to a deactivating =C=O.

Is this reasoning ok?

thnks
 
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You got it.
 
nice... thnks
 

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