Talk:Diazomethane

Structure and bonding

I'll do this soon if no one else beats me to it: discussion of the structure of and bonding in diazomethane.

Compare the following:

• diazomethane (CRC), H₂CNN, r(C-N) = 132 pm, r(N-N) = 112 pm

• azomethane (CRC), H₃C-N=N-CH₃, r(C-N) = 148.2 pm, r(N-N) = 124.7 pm

• benzenediazonium chloride 1963, [PhN₂]Cl, r(C-N) = 138.5 pm, r(N-N) = 109.9 pm

r(CN): diazomethane (partial double) < benzenediazonium (single) < azomethane (single)

r(NN): benzenediazonium (triple) < diazomethane (partial triple) < azomethane (double)

In the conjugated pi system, there are 4 pi electrons in 3 pi orbitals:

Ben (talk) 16:04, 24 May 2009 (UTC)

I think that a lot of readers would be interested in some description of the bonding. It's a cumulene related to N₂O, but basic at C, hence its reactivity. I always found this molecule counterintuitive.--Smokefoot (talk) 19:51, 24 May 2009 (UTC)

cyclic redirect "Diazald"

The internal link to N-methyl-N-nitroso-p-toluenesulfonamide (Diazald) comes back to the Diazomethane page via redirect. Please solve this problem by opening a page for CAS 80-11-5 (N-methyl-N-nitroso-p-toluenesulfonamide or Diazald).131.220.65.210 (talk) 14:02, 13 May 2013 (UTC)

External links modified

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Detail-level of section "Safety"

The paragraph on microfluidics adds way too much detail. I suggest to remove the whole paragraph (or at least shorten it massively).

Proof-of-concept work has been done with microfluidics, in which continuous point-of-use synthesis from N-methyl-N-nitrosourea and 0.93M potassium hydroxide in water was followed by point-of-use conversion with benzoic acid, resulting in a 65% yield of the methyl benzoate ester within seconds at temperatures ranging from 0-50 C. The yield was better than under capillary conditions; the microfluidics were credited with "suppression of hot spots, low holdup, isothermal conditions, and intensive mixing." Trepanatio (talk) 17:00, 18 August 2019 (UTC)