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Topic: Resonance structure of molecule  (Read 2417 times)

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Offline owlpower

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Resonance structure of molecule
« on: October 01, 2018, 12:40:53 AM »
I am having trouble drawing the resonance structure here.

I can't see where to draw my curved arrows. I know that N is most electronegative here, so I am aiming for my negative charge to be on N.
Any hints is much appreciated.

Offline mjc123

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Re: Resonance structure of molecule
« Reply #1 on: October 01, 2018, 04:57:12 AM »
You are aiming wrongly. What happens when the lone pair of N becomes involved in the delocalisation?

Offline owlpower

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Re: Resonance structure of molecule
« Reply #2 on: October 01, 2018, 10:14:39 AM »
If the lone pair takes part in delocalisation, then N will have a positive charge.

Offline Babcock_Hall

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Re: Resonance structure of molecule
« Reply #3 on: October 01, 2018, 11:57:43 AM »
In the structure for the ammonium ion, there is a formal positive charge on nitrogen.  There are many compounds which have a formal positive charge on oxygen as well.  Therefore, I would not rule out a structure solely on the basis that an electronegative atom has a positive charge.  I acknowledge that when deciding on which resonance forms make a large or a small contribution to overall resonance hybrid, that several factors come into play.

Offline owlpower

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Re: Resonance structure of molecule
« Reply #4 on: October 03, 2018, 10:23:26 AM »
https://imgur.com/a/gZFm5Zv

Thank you for the input, I came up with these resonance structures!

Offline mjc123

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Re: Resonance structure of molecule
« Reply #5 on: October 03, 2018, 11:57:14 AM »
The one with 4 charges is highly improbable!

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