Comments on: What Factors Destabilize Free Radicals? https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/ Tue, 30 Aug 2022 08:13:59 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-556580 Thu, 20 Jun 2019 16:48:09 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-556580 In reply to saumya.

Alkyl radicals are usually sp2 hybridized. Eg the methyl radical is sp2 hybridized. Sp3 hybridized free radicals would form from bridgeheads incapable of flattening, such as adamantyl. They can be formed, but are less stable.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-556579 Thu, 20 Jun 2019 16:47:09 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-556579 In reply to Vaibhav jain.

Simple alkyl radicals prefer a planar shape. For example the methyl radical adopts a planar geometry as shown by ESR spectra and other studies. See. https://www.nature.com/articles/2221123a0 . These are sp2 hybridized. However radicals can also be formed on bridgeheads, which are incapable of planarity. These radicals are harder to form and cam be thought of as sp3 hybridized. See. https://pubs.acs.org/doi/abs/10.1021/ja00048a005 .

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By: Shaikh Rahil https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-556271 Wed, 12 Jun 2019 06:11:50 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-556271 But what about captodative effect its say that free radical is stabilies by E.R.G & E.W.G ALSO so please explain me ?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-552483 Fri, 12 Apr 2019 18:54:52 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-552483 In reply to Anon.

Thank you very much for this comment. Aren’t most alkyl radicals shallow pyramidal though?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-552481 Fri, 12 Apr 2019 18:53:11 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-552481 In reply to Kat.

Glad to hear it Kat!

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By: Anon https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-550000 Thu, 14 Mar 2019 10:23:59 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-550000 When you combine the LUMO of an EWG with the SOMO of a radical, you get a lowering of the SOMO energy and therefore stabilisation. The fluoromethyl radical you cite is indeed less stable than the corresponding methyl radical, but this is because the shape of the radical goes from planar(ish) to more pyramidal, meaning that the radical is more sigma in character than pi. See Organic Chemistry Clayden et al Oxford University Press (2nd Ed) P. 1025-1027

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By: Vaibhav jain https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-505458 Sun, 19 Feb 2017 17:50:39 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-505458 In reply to Q.

I think one reasoning could be that of C were sp3 the orbital in which the unpaired electron was resting had some s character and if it were sp2 the electron has pure p orbital which relative further from pure s orbital

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By: Kat https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-504969 Tue, 14 Feb 2017 21:17:28 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-504969 Just wanted to say a big thanks!

This page (and the few before it) have been an unbelievable help :)

Everything is well laid out and sufficiently explained!

Kat

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By: saumya https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-427938 Wed, 30 Sep 2015 17:08:50 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-427938 Sir i have question..in which case there will be the formation of sp2 free radical n sp3 free radical.??

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By: James https://www.masterorganicchemistry.com/2013/08/05/what-factors-destabilize-free-radicals/#comment-421878 Fri, 04 Sep 2015 20:43:01 +0000 https://www.masterorganicchemistry.com/?p=7464#comment-421878 In reply to R.

Readily available information. I’d refer you to Carey & Sundberg A, or March’s Advanced Organic Chemistry for further discussion.

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