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

Hello fellow Wikipedians,

I have just added archive links to one external link on Diazomethane. Please take a moment to review my edit. If necessary, add {{cbignore}} after the link to keep me from modifying it. Alternatively, you can add {{nobots|deny=InternetArchiveBot}} to keep me off the page altogether. I made the following changes:

• Added archive http://web.archive.org/web/20110606083207/http://www.sigmaaldrich.com/etc/medialib/docs/Aldrich/Bulletin/al_techbull_al180.pdf to http://www.sigmaaldrich.com/etc/medialib/docs/Aldrich/Bulletin/al_techbull_al180.pdf

When you have finished reviewing my changes, please set the checked parameter below to true or failed to let others know (documentation at {{Sourcecheck}}).

This message was posted before February 2018. After February 2018, "External links modified" talk page sections are no longer generated or monitored by InternetArchiveBot. No special action is required regarding these talk page notices, other than regular verification using the archive tool instructions below. Editors have permission to delete these "External links modified" talk page sections if they want to de-clutter talk pages, but see the RfC before doing mass systematic removals. This message is updated dynamically through the template {{source check}} (last update: 18 January 2022).

• If you have discovered URLs which were erroneously considered dead by the bot, you can report them with this tool.
• If you found an error with any archives or the URLs themselves, you can fix them with this tool.

Cheers.—^{cyberbot II}_{Talk to my owner:Online} 14:33, 28 February 2016 (UTC)

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)