Nitrene Definition – Hybridization & Examples

Table of Contents

Nitrene Definition: Nitrenes are electron deficient and reactive intermediates, in which the structure of nitrene reveals that there are six electrons around nitrogen. These are nitrogen analogs of carbene and hence something referred to as azo carbene.

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Nitrene Hybridization

Nitrenes are nitrogen analogues of carbenes. The nitrogen atom possesses only six electrons; in nitrenes, the triplet state is lower in energy than the singlet state.

Nitrene Hybridization

Nitrene Examples

Nitrene Examples

Singlet and triplet nitrenes

Singlet nitrene is a kind of nitrene in which unshared electrons are paired. It is represented as:

Siglet Nitrene
Singlet nitrene is less stable form.

Triplet nitrene is a nitrene in which unshared electrons are not paired. It is represented as:

Triplet nitrene
Triplet nitrene is thus free radical.

Generation/ Formation of Nitrene

  • By the reduction of nitro compound with trialkoxy phosphite
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  • By α-elimination reaction
Formation of nitrene

Reactions of Nitrene

  • Addition to C=C double bond
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The addition of singlet nitrene is stereospecific.
  • Rearrangement reaction
reaction of nitrene
  • Dimerization
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Azobenzene is often obtained by the dimerization of aryl nitrenes.

Carbene and Nitrene

Carbenes are very short-lived species or reactive species in which the carbon atom has two bond pairs and two unshared electrons.

FAQs/Mcqs

What is nitrene?

Nitrenes are electron deficient and reactive intermediates, in which the structure of nitrene reveals that there are six electrons around nitrogen.

Nitrene

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