Comments on: 5 Key Basicity Trends of Amines

By: Seo DongBin

Seo DongBin — Mon, 25 Sep 2023 06:57:09 +0000

sir, why is basicity NH3 < aniline in gas phase? Nitrogen of NH3 is sp3 and aniline is sp2.
And, why is basicity aniline < NH3 in water?

By: James Ashenhurst

James Ashenhurst — Wed, 23 Nov 2022 14:25:23 +0000

In reply to Armaan Ahmed. Thanks for the catch. Fixed!!

By: Armaan Ahmed

Armaan Ahmed — Tue, 22 Nov 2022 14:51:05 +0000

Hi James,
In the summary card/diagram, you say that basicity increases with increasing s character. But it should say “decreasing” s-character like you did below.

By: James Ashenhurst

James Ashenhurst — Wed, 03 Aug 2022 21:27:41 +0000

In reply to Harsh Darji. The key point is that in diphenylamine the lone pair on nitrogen can be delocalized through two aromatic rings. Maybe I'm not fully grasping your question, but this doesn't appear to have any significant impact on the resonance (or aromaticity) of the aromatic rings, given the low value obtained for the pKa of protonated diphenylamine.

By: jahangeer khan

jahangeer khan — Thu, 21 Jul 2022 18:36:17 +0000

sir. i am working on oleylamine ligand but it is hard acidity. i like to convert into softer amine ligand bu screening its tail. whats your suggestion to got softer oleylammonium ion for interaction with soft iodide in CsPbI3 QDs structure

By: Harsh Darji

Harsh Darji — Thu, 20 Jan 2022 08:56:29 +0000

The subpoint no.2, in point 3 – How’s aniline more basic (i.e. less acidic) than the other compound (with 2 benzene rings) ? Doesnt the lone pair get distributed on both rings as opposed to one? And if that happens then neither of the rings will have good resonance. But with Aniline that’s not the case. Kindly clarify my confusion. Thank you :).

By: James Ashenhurst

James Ashenhurst — Fri, 22 Oct 2021 20:59:41 +0000

In reply to Natalia Pontesta.

Hi Natalia – they should be about the same order of magnitude. This table on Herbert Mayr’s site may be useful. https://www.cup.lmu.de/oc/mayr/reaktionsdatenbank/fe/showclass/41

By: Natalia Pontesta

Natalia Pontesta — Wed, 20 Oct 2021 06:16:12 +0000

Thank you very much for the quick reply, I am really interested in the nucleophilic capacity of these compounds, I have read that basicity and nucleophilic capacity are related, in this case does the chain length affect the nucleophilic capacity or is it still negligible?

By: James Ashenhurst

James Ashenhurst — Tue, 19 Oct 2021 16:03:55 +0000

In reply to Natalia Pontesta. They have negligible difference in basicity, within a factor of 10.

By: Natalia Pontesta

Natalia Pontesta — Tue, 19 Oct 2021 08:50:24 +0000

Dear Dr James
I am working with propylamine and octylamine, Tthe difference between them is the carbonate chain, but which one is more basic