Sciencemadness Discussion Board

Sulphuric imide?

chornedsnorkack - 31-3-2024 at 03:08

Sulphur is capable of giving double bonds.
These include:
  1. sundry thiones, with bonding R2C=S
  2. sulphines, notoriously cis-CH2=CH-C=S=O - the onion smell
  3. sulphenes, with bonding R2C=SO2

But are there any compounds with N=S double bond?
What would be the name of a compound HN=SO2, and is it stable? If not, what is the decay mechanism? Do substituted compounds RN=SO2 exist, and what are they called?

bnull - 31-3-2024 at 04:29

There are sulfinamidines (R2=N-(S=N-R)-R) and sulfonimidamides (R2N-(S=O)=N-R(-R), with the R not necessarily equal. And also the sulfimides as explained below.

If I'm not tripping on the IUPAC rules, the wossname (HN=SO2) is called sulfonylideneamine or sulfimide, with the corresponding N-alkyl- or N-aryl-sulfonylideneamines (or sulfimides), or both, for the RN=SO2. N-Methyl-sulfimide, for example, is H3C-N=SO2.

I'd say that
  1. they're more of theoretical than practical interest;
  2. or the ones that are the focus now have the sulfimide units as "appendages", with the R as a large, heavily substituted molecule.

It seems that interest in them was relatively high in the first half of the 1970s, was pretty low until the late 2000s, when it made a sort of comeback that lasted until about 2015, 2016, and seems to have died since then. I say that because of the number of published papers with "(something-with-a-long-name)sulfimide" in the title. Sigma-Aldrich may be selling these compounds by milligrams, if you're lucky (or wealthy) enough.

Edit: I hate my typos.

[Edited on 31-3-2024 by bnull]