Comments on: How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge) https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/ Fri, 23 Aug 2024 01:15:06 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: xiao liu https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-703896 Fri, 23 Aug 2024 01:15:06 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-703896 I am confused about the partial charge according to the electronegativity of the element.

You say ” In a bond, the more electronegative element will have a greater share of the electrons, and a partial negative charge to reflect this greater electron density. The less electronegative element will have a partial positive charge to reflect the lack of electron density. ”

However, According to https://www.reed.edu/chemistry/ROCO/Potential/charge_distribution.html, it seems like for HO3+, either hydrogen and oxygen are positive. The only difference is that oxygen bears less positive charge compared with hydrogel because of the difference of electronegativity.

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By: How Do We Know Methane (CH4) Is Tetrahedral? | Straight A Mindset https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-674731 Tue, 17 Oct 2023 22:36:29 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-674731 […] that each C–H bond has a small dipole due to the difference in electronegativity between C (2.5) and H (2.2). We expect C to be […]

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By: | Straight A Mindset https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-674721 Tue, 17 Oct 2023 21:17:01 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-674721 […] that each C–H bond has a small dipole due to the difference in electronegativity between C (2.5) and H (2.2). We expect C to be […]

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-648614 Tue, 21 Feb 2023 16:58:07 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-648614 In reply to Ayush sharma.

It does form hydrogen bonds, they are just fairly weak. Probably due to poorer orbital overlap between H and Cl than is found between H and F (3p vs 2p)

For example Eric Jacobsen’s research program involves using very weak interactions between hydrogen bonded catalysts (such as ureas) and chlorines. It has to use very non-coordinating solvents so that they don’t interfere with these weak interactions.

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By: Ayush sharma https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-648455 Sun, 19 Feb 2023 03:32:01 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-648455 F-4.0
0-3.4
cl-3.2
N-3.0
Then logically cl as also being more electronegative than N (form H bonding)
should also forms H bonding .
But it doesn’t . Why ???????

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-644312 Wed, 14 Dec 2022 09:50:28 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-644312 In reply to Kevin Truong.

Late to this, but this is a typo. Will fix. Thank you!

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By: Kevin Truong https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-579647 Mon, 27 Apr 2020 05:19:58 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-579647 Hi James

In the last diagram I see you depict an interaction between NH4- and H20. I could not find any info about NH4 anion, was it a typo or it has other meaning? Please help me clarify this compound, thanks !

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-574629 Fri, 10 Jan 2020 05:17:21 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-574629 In reply to Chris Orazulike.

Not necessarily, because in the process of one species donating an electron pair to another, the acceptor molecule may expel a species bearing a lone pair of electrons. Acid base reactions are a simple example. In the reaction of NaOH with HCl, the hydroxyl group donates a pair of electrons to H, but Cl accepts a pair of electrons (from the H-Cl bond). Neither oxidation nor reduction has taken place. This is also true of substitution reactions.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-547550 Mon, 11 Feb 2019 16:51:45 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-547550 In reply to Jordan.

I dunno Jordan. Look at the charge distribution map of H3O+ and look for the blue areas (positive charge). They’re all on hydrogen. http://www1.lsbu.ac.uk/water/hydrogen_ions.html

Nucleophiles *can* attack oxygen, if it’s attached to a decent leaving group. For instance, look at the migration step in hydroboration-oxidation. The key is that oxygen must have a low-lying sigma* orbital that can be attacked by a nucleophile. That’s not present here in H3O+ because a nucleophile would have to liberate H– , although that specific point is a bit beyond the topic at hand.

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By: Jordan https://www.masterorganicchemistry.com/2011/11/15/how_to_use_electronegativity/#comment-546807 Sat, 26 Jan 2019 21:21:34 +0000 https://www.masterorganicchemistry.com/?p=2941#comment-546807 Interesting, useful. But, to say thet the oxygen in hydronium is partiall negative is incorrect. It is less partially positive than H, but it is not negative. The important reason why nucleophiles do not attack oxygen is that this leads to thermodynamically disfavored intermediates for reasons of formal charge/octet rule.

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