Question

Explain why, when the guanidino group of arginine is protonated, the double-bonded nitrogen is the nitrogen that accepts the proton. There is a scheme of a reversible reaction, where one equivalent of the reactant reacts with two equivalents of H plus. The reactant is H2NCNHCH2CH2CH2CHCO minus, with an NH group, with a lone pair at the N atom, double-bonded to the first (from left to right) carbon, an NH2 group attached to the fifth carbon, an O atom double-bonded to the sixth carbon and a lone pair of electrons at the first and the second N atoms of the chain. The product has the same structure as the reactant, except that not an NH group with a lone pair, but an NH2 plus group is double-bonded to the first carbon. In addition, an NH3 plus group is attached to the fifth carbon instead of the NH2 group.

Answer 1

Due to the resonance structures

Step-by-step explanation:

In the question:

"Explain why, when the guanidino group of arginine is protonated, the double-bonded nitrogen is the nitrogen that accepts the proton. There is a scheme of a reversible reaction, where one equivalent of the reactant reacts with two equivalents of H plus"

We have to take into account the structure of the amino acid arginine. In which, we have the amino and the carboxylic groups in the right and the guanidine group in the left.

In this group, we have a central carbon with three nitrogen atoms around and a double bond with the nitrogen on the top. This nitrogen on the top will accept the proton because the structure produced will have a positive charge on this nitrogen. Then, the double bond with the carbon can be delocalized into the nitrogen producing a positive charge in the carbon.

In this structure (the carbocation), we can have several resonance structures. In the blue option, we can produce a double bond with the nitrogen on the right. In the purple option, we can produce a double bond with the nitrogen on the left.

In conclusion, if the nitrogen in the top on the guanidine group accepts an hydrogen atom and we will have several resonance structures that can stabilize the molecule. Due to this, the nitrogen in the top its the best option to accept hydrogens.

See figure 1

I hope it helps!