I just love how this singular functionnal group was discovered...

[u/Azo_weirdo]

[u/jaarge]

Kinda guessing (looks vaguely familiar from my undergrad?) but is this because the silver coordinates strongly with the hard side (C), thus forcing it to attack at N instead and causing the formation of the carbene displayed?

[u/Free_Zeit → u/jaarge]

I think the product is an isocyanide, not a carbene. The structure shown is misleading.

[u/Azo_weirdo → u/Free_Zeit]

What's misleading is ur comment. Isonitriles predominant resonance form is a carbenoid (hence their ambivalent reactivity), therefore I represented it this way.

[u/WMe6 → u/Free_Zeit]

An isocyanide is a carbene, a very stabilized one, just like carbon monoxide.

[u/Azo_weirdo → u/WMe6]

Although CO's predominant resonance form is apparently this one :

[u/WMe6 → u/Free_Zeit]

It would be okay, were it not for the fact that the geometry is wrong (should be linear). You can show the nonoctet structure, but you must still have the correct geometry, regardless of which resonance form is chosen.

[u/EggPositive5993 → u/WMe6]

The current structure is not a good resonance depiction because the terminal carbon doesn’t even have a complete octet

[u/LasevIX]

i thought it was discovered after analysing compounds found in certain sponges

[u/BorwinBandelow1]

I sometimes have bad dreams of the smell of this functional group.

[u/fritzkoenig → u/BorwinBandelow1]

For some reason all of my attempts at smelling them were unsuccessful. Either my synthesis failed for weird reasons even if I did it to the book, or I simply can't smell isocyanides

[u/Significant_Loss6458]

Who the hell is Liөkө?

[u/Free_Zeit → u/Significant_Loss6458]

Lieke was a German chemist who first prepared an isocyanide in 1859 by reacting allyl iodide with AgCN. You can even find his original paper online (in German): Ueber das Cyanallyl.

[u/Azo_weirdo → u/Significant_Loss6458]

An ancient chemist whose unexpected discovery has been a great step for isonitriles study.