Thursday, 28 January 2016

organic chemistry - Hybridisation of terminal nitrogen in diazomethane


I have a few questions about the terminal nitrogen (highlighted in red) in diazomethane, $\ce{CH2N2}$.


Diazomethane




  1. Is that nitrogen $\mathrm{sp}$ or $\mathrm{sp^2}$ hybridised?





  2. What type of orbitals do the lone pairs on that nitrogen reside in?




  3. Does the negative charge on nitrogen undergo resonance?





Answer



In da wikipedia you can see that the C=N=N fragment is linear AND another resonance structure involves triple N-N bond. So, the answers



  1. it is sp in one resonance structure and probably sp2 in another resonance structure.


  2. depends on the resonance structure considered

  3. yep.


Diazomethane typically reacts with its negatively charged carbon, so this is of little consequence though.


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