HypervalencyChemical BondingChemistryDiazoDiazo CompoundsChemical Sciences

Are diazomethanes hypervalent molecules? An attempt into more insight by more “tuning” with substituents.

https://doi.org/10.59350/1jy8d-p6961
Published in Henry Rzepa's Blog

Recollect the suggestion that diazomethane has hypervalent character[cite]10.1039/C5SC02076J[/cite]. When I looked into this, I came to the conclusion that it probably was mildly hypervalent, but on carbon and not nitrogen. Here I try some variations with substituents to see what light if any this casts.

References

General Chemistry

A quantitative definition of hypervalency

https://doi.org/10.1039/c5sc02076j
Published in Chemical Science

The concept of hypervalency has had a long but troubled history. Although several attempts have been made to dispense with the concept altogether, it remains in widespread use. By developing a simple but quantitative measure of hypervalency, the concept can be rehabilitated to provide valuable chemical insights in the context of Lewis models.