JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
The “N” which does not contribute to the basicity for the compound is : 

- AN 7
- BN 9
- CN 1
- DN 3
View written solutionFree
Correct answer: B
-
Identify the structure and the labeled nitrogens
The question refers to a fused heterocyclic system with nitrogens labeled and (as in purine-type numbering).
We must find which nitrogen does not contribute to basicity.
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Principle of basicity in heterocycles
A nitrogen contributes to basicity if its lone pair is available for protonation.
- Pyridine-like nitrogen: lone pair is outside the aromatic sextet, so it is available for protonation basic.
- Pyrrole-like nitrogen: lone pair is part of the aromatic sextet, so it is not available for protonation does not contribute to basicity.
-
Examine the labeled nitrogens
In the purine framework:
- and are pyridine-like nitrogens. Their lone pairs are not part of the aromatic sextet, so they can accept a proton.
- is also pyridine-like, so its lone pair is available for protonation.
- is pyrrole-like. Its lone pair participates in maintaining aromaticity of the imidazole-like ring.
Therefore, protonating would disrupt the aromatic electron delocalization, so this lone pair is not available for basic behavior.
-
Conclusion
The nitrogen that does not contribute to basicity is:
-
Option check
- A: contributes to basicity
- B: does not contribute to basicity
- C: contributes to basicity
- D: contributes to basicity
Hence, the correct option is B.
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