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Question

Which one of the following compound is analogue of benzene ?

The correct answer is
Trimeric cyclophosphazene

Benzene Analogue Identification: Trimeric Cyclophosphazene

The question asks us to identify which compound among the given options acts as an analogue of benzene.

Understanding Benzene and Analogues

Benzene is a fundamental organic compound with the chemical formula $ C_6H_6 $. Its structure consists of a hexagonal ring of six carbon atoms, with each carbon atom bonded to one hydrogen atom. The ring is characterized by delocalized pi electrons, giving it unique stability known as aromaticity.

An analogue in chemistry refers to a compound that has a similar structure or similar chemical properties to another compound. In this case, we are looking for a compound that shares key structural features with benzene, particularly a stable ring structure.

Analysis of Options

  • Diborane ($ B_2H_6 $): Diborane is an inorganic compound consisting of two boron atoms and six hydrogen atoms. It exists as a dimer and does not possess a stable ring structure comparable to benzene. Therefore, it is not an analogue of benzene.
  • Tetrameric cyclophosphazone: This term is less common. However, compounds related to phosphazenes exist. Tetrameric cyclophosphazenes have the general formula $ (NPX_2)_4 $, featuring a ring structure. While related, the trimeric form is more frequently cited as a direct analogue.
  • Carborane: Carboranes are fascinating clusters containing carbon atoms along with boron atoms, often forming cage-like structures (e.g., closo-dicarbadodecaborane, $ C_2B_{10}H_{12} $). While some carboranes exhibit aromatic-like properties due to delocalized bonding, their structure is fundamentally different from the planar, six-membered ring of benzene.
  • Trimeric cyclophosphazene: These compounds have the general formula $ (NPX_2)_3 $. They feature a six-membered ring composed of alternating phosphorus (P) and nitrogen (N) atoms. This ring structure is isoelectronic with the six-membered carbon ring ($ C_6 $) in benzene. Both have six atoms in the ring and possess delocalized pi electrons, leading to considerable stability. The structure and electronic properties make trimeric cyclophosphazene a well-recognized inorganic analogue of benzene.

Conclusion

Based on the structural similarity, particularly the presence of a six-membered ring with delocalized electrons, Trimeric cyclophosphazene ($ (NPX_2)_3 $) is considered the closest analogue to benzene ($ C_6H_6 $) among the given options.

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Important Questions from Heterocyclic Compounds

  1. Furan has ____________ Π e- plus an unshared pair of oxygen sp2 orbital.

  2. For the two statements given below, analyse for the following:

    (a) Pyridine and Pyrrole both are weak bases, but pyridine is much more basic than pyrrole.

    (b) Lone pair associated with nitrogen in Pyridine is entirely with nitrogen and not delocalised into the aromatic Π system, whereas in Pyrrole unshared pair belonging to nitrogen must be added to the 4Π e- of 2 double bonds and thus is delocalised into the aromatic Π system.

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