The official structure of fulminate looks like this: from wikipedia: https://en.wikipedia.org/wiki/Fulminate

However, this structure does not minimize formal charge, since nitrogen has a formal charge of +1, while carbon has a formal charge of -1.

Instead, it would make more sense for fulminate to look like this: enter image description here

In this structure, the nitrogen and carbon now both have formal charges of zero, and the number of electrons is the same as the official structure.

Carbon seems like it can exist with six electrons, as shown in https://en.wikipedia.org/wiki/Dichlorocarbene. However, the article says that it is an intermediate.

My question is, why is the first structure of fulminate the official one and not the second one? Does the octet rule take precedence in this case?

  • 2
    $\begingroup$ The carbon has six electrons, that's a no-no. $\endgroup$ Dec 28, 2018 at 3:40
  • $\begingroup$ Oh... right... I forgot about the octet rule $\endgroup$
    – chemN00b
    Dec 28, 2018 at 3:44
  • $\begingroup$ For now, read "intermediate" as a fancy way to say "does not exist". $\endgroup$ Dec 28, 2018 at 5:53
  • $\begingroup$ chemistry.stackexchange.com/questions/34078/… $\endgroup$
    – Mithoron
    Dec 28, 2018 at 17:27
  • $\begingroup$ @orthocresol: Not necessarily; stable/persistent carbenes exist. $\endgroup$
    – Vikki
    Mar 31, 2019 at 3:28


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