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Chapter 16: Q17P (page 822)

Show which of the nitrogen atoms in purine are basic, and which one is not basic. For the nonbasic nitrogen, explain why its nonbonding electrons are not easily available to become protonated

Short Answer

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Purine with basic and non-basic nitrogen

Step by step solution

01

Purine

Purines are heterocyclic aromatic organic compounds is comprised of two rings that are fused together. These rings contain nitrogen atoms which can be acidic or basic.

02

Acidic or basic nitrogen in purine

In general basic nitrogen is those which can donate its lone pair of electrons to acid. In purine base the two nitrogen of six-member ring are basic and one nitrogen of five-membered ring non-basic. The nonbonding electrons of nonbasic nitrogen are used in the ring for delocalization. Hence they are not available for protonation, thus, they are non-basic.

Purine with basic and non-basic nitrogen

The delocalization of nitrogen electrons in purine is represented as follows:

Delocalization of electrons

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