Help need titration curve for Arginine

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In the discussion about the titration curve for Arginine at low pH, the main question revolves around whether the two nitrogen atoms, aside from the one bonded to the carboxylate group, can gain additional protons, potentially increasing the charge beyond +2. It is noted that the terminal C(=NH)-NH2 group is unlikely to accept additional protons due to its amphoteric nature. However, a referenced source suggests that this group can indeed protonate, maintaining a +2 charge. This indicates a nuanced understanding of Arginine's behavior in acidic conditions, emphasizing the complexity of its protonation states. The shared resource is recommended for further clarification on the topic.
Daemos
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I have a question

When you do a titration curve for Arginine and you start it off in the acid exteme (low pH) does it gain anymore Hydrogens other than the one that always bonds to the COO- group? (so does it gain more than a +2 charge)

To rephrase, do any of the other two Nitrogens (other than the one double bonded to the Carbon in the R-Group) gain additional hydrogens when it acts as a base.
 
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Yes, the formula should be written in low pH like that:

HOOC-CH(NH_3)^+-(CH_2)_3-NH_2^+-C(=NH)-NH_2

I don't think that the terminal C(=NH)-NH2 group takes additional protons, since they seem to be amphoteric.

But I have found this http://www.cem.msu.edu/~reusch/VirtualText/proteins.htm, mentioning that the C=NH group protonates instead to give the same 2+ charge, which is logical as the nitrogen I mentioned is somewhat hindered to react with proton.

I feel confident that the website will help you very much; I've liked it too.

Take care.
 
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thanks a lot for the info :)
 
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