Why does fulminate not minimize formal charge in its structure?

Ask Question

Asked 2 years, 2 months ago

Active 2 years, 2 months ago

Viewed 125 times

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:

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?

asked Dec 28 '18 at 3:25

chemN00b

1761 silver badge10 bronze badges

1

$\begingroup$ The carbon has six electrons, that's a no-no. $\endgroup$ – orthocresol♦ Dec 28 '18 at 3:40
$\begingroup$ Oh... right... I forgot about the octet rule $\endgroup$ – chemN00b Dec 28 '18 at 3:44
$\begingroup$ For now, read "intermediate" as a fancy way to say "does not exist". $\endgroup$ – Ivan Neretin Dec 28 '18 at 5:53
$\begingroup$ chemistry.stackexchange.com/questions/34078/… $\endgroup$ – Mithoron Dec 28 '18 at 17:27
$\begingroup$ @orthocresol: Not necessarily; stable/persistent carbenes exist. $\endgroup$ – Vikki - formerly Sean Mar 31 '19 at 3:28

Add a comment |

0 Your Answer

Name

Required, but never shown

Post as a guest

Name

Required, but never shown

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy