Comments on: Resonance Structures: Negative Charges Are Best Placed On The Least Basic Atom https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/ Fri, 16 Jan 2026 20:35:36 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: BJ https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-581592 Fri, 26 Jun 2020 14:58:11 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-581592 One last question: Based on the last point on hybridization, is it safe to say we cannot use hybridization to determine stability between resonance forms?

]]> By: BJ https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-581590 Fri, 26 Jun 2020 14:36:38 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-581590 Ah! I may have figured this out. Correct me if I am wrong, but isn’t the fact that the those negative charges are able to participate in resonance mean that we can ignore the alpha effect? When looking back at Klein’s explanation the lone pairs that were adjacent to each other could not move via resonance, hence, it is my suspicion that when dealing with inductive effects we need only worry about the alpha effect if the electrons in the negative charge are unable to move via resonance.

]]> By: BJ https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-581588 Fri, 26 Jun 2020 14:23:18 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-581588 When discussing the inductive effect, why would those EWG directly adjacent to the negative charge stabilize it?As you stated in your note 1 there would be some repulsion,however, I read in Klein’s Organic Chemistry I:Translating the Basic Concepts that a lone pair adjacent to a lone pair is called the “alpha effect” which is a destabilizing effect.

]]> By: ashish https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-581457 Mon, 22 Jun 2020 20:03:25 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-581457 Both nitrogen atoms are, in fact, sp2 hybridized, and their stabilities cannot be distinguished based on this characteristic

shoudnt the right nitrogen be sp hybridised as it is in the right resonance form
also please explain note 1

]]> By: ashish https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-581454 Mon, 22 Jun 2020 19:55:52 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-581454 a very wonderful explanation indeed
could you explain your note 1 please
it should also be pointed out that theres going to be some repulsion in charge between the oxygen & negative charge or the fluorines & negative charge. Furthermore once the electron withdrawing group can participate in resonance we have to think about π donation and π accepting.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-570747 Fri, 15 Nov 2019 15:44:28 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-570747 In reply to Mili Litvajova.

Yes there should be! This is in line to be fixed.

]]> By: Mili Litvajova https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-530296 Sat, 31 Mar 2018 09:28:03 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-530296 Hi James,
I love your blogs! What a great way to refresh my org chem!
I was just thinking, regarding Note 2 where you discuss hybridization, shouldn’t there be a H in alkene? e.g. -CH3 < -CH=CH2 < -C triple bond CH

]]> By: Ryan Peterson https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-467999 Sat, 16 Jul 2016 20:07:00 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-467999 In the bottom example why is the nitrogen on the right considered to be sp2 when the Hybridization rule is Number of attached atoms (2 in this case, hydrogen and nitrogen) and 2 lone pairs. 2 plus 2 is 4 orbitals or sp3?

]]> By: Sarmistha https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-49286 Sat, 23 Nov 2013 04:13:38 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-49286 In reply to James Ashenhurst.

Point taken. :-)

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/12/13/resonance-structure-negative-charge-least-basic-atom/#comment-49282 Sat, 23 Nov 2013 03:42:01 +0000 https://www.masterorganicchemistry.com/?p=3577#comment-49282 In reply to Sarmistha.

Look at the figure drawn. Is there an aromatic ring drawn anywhere? No. It is an isopropyl group. If an aromatic group was there, then, yes, the diazonium form would be more stable, because the diazo form disrupts aromaticity. But an aromatic group is NOT drawn. It is an alkyl diazo compound. Very different. I don’t understand why aromatic rings are being brought up in this discussion.

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