Thursday, January 2, 2020

The Lewis structure for NCO-


I was having trouble drawing the Lewis structure for $\ce{NCO^-}$. I found this image online:


enter image description here


But why is structure number one preferred over structure number two? Why does carbon prefer to have a triple bond with nitrogen, rather than have a double bond with nitrogen and a double bond with oxygen?



Answer



If you count electrons and determine the formal charge on each atom, you find that in structure #1, the negative charge is on the oxygen. Do the same exercise for structure #2 and you find that the negative charge is on nitrogen. Since oxygen is more electronegative then nitrogen, the negative charge is more stable when its on the oxygen atom. Therefore, structure #1 is more stable (preferred) than structure #2.


Structures #3-#5 are even less stable. They either violate the octet rule (#4, #5) and / or have charges (sometimes multiple) on more than one atom (#3-#5).


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