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Question
Why does R3P=O exist but R3N=O does not (R = alkyl group)?
Solution 1
N (unlike P) lacks the d-orbital. This restricts nitrogen to expand its coordination number beyond four. Hence, R3N=O does not exist.
Solution 2
Nitrogen does not contains d-orbitals. As a result, it cannot expand its covalency beyond four and cannot form pπ – dπ multiple bonds. In constrast, P contains the d-orbitals, and can expand its covalency beyond 4 and can form pπ-dπ multiple bonds. Hence R3P = O exist but R3N = O does not.
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