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alexandr1967 [171]
3 years ago
6

Explain why, when the guanidino group of arginine is protonated, the double-bonded nitrogen is the nitrogen that accepts the pro

ton. 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.

Chemistry
1 answer:
Jet001 [13]3 years ago
7 0

Answer:

Due to the resonance structures

Explanation:

In the question:

"<em>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</em>"

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

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 (<u>the carbocation</u>), we can have several resonance structures. In the <em>blue option</em>, we can produce a double bond with the nitrogen on the right. In the <em>purple option</em>, 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 <u>several resonance structures that can stabilize the molecule.</u> Due to this, the nitrogen in the top its the best option to accept hydrogens.

See figure 1

I hope it helps!

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