How to predict the regioselectivity of an organic reaction ?

mekelleche · 发表于 Post on 2020-9-25 18:40:44

Hi everyon ?
I would like to ask about the quantum methods used to predict the reactive sites of an organic molecule in purpose to study the regioselectivity of a reaction ?
Note : Other methods than Conceptual DFT, Parr index and Fukui index.

Sincerely,
Mekelleche

wzkchem5 · 发表于 Post on 2020-9-25 19:28:55

Electrostatic potentials, atomic charges, atomic spin densities, just to name a few.
But after all the most convincing evidence comes from an actual calculation of the reaction barriers. Even barriers at the semiempirical level prove more reliable than conceptual DFT or population analysis descriptors at the DFT level, as long as the semiempirical electronic structure is qualitatively correct.

wangzhe · 发表于 Post on 2020-9-25 19:47:17

I think the energy barrier and spin densities are the strong evidence for the selectivity.

sobereva · 发表于 Post on 2020-9-26 10:17:47

Please check Section 4.A.4 of Multiwfn manual, there is a comprehensive review of available methods that can be used in predicting reactive sites.

mekelleche · 发表于 Post on 2020-9-26 21:09:11

本帖最后由 mekelleche 于 2020-10-3 06:05 编辑

Dear All,
Thank you very much for your replies. Professor Tian Lu, the van der Waals surface (please see photo from your article) could give me a useful informations in this context.

Many thanks
Sincerely,
Mekelleche

mekelleche · 发表于 Post on 2020-10-3 18:29:02

Please Professor Tian Lu, is it possible to use the van der Waals surface ?

wzkchem5 · 发表于 Post on 2020-10-4 14:21:28

mekelleche 发表于 2020-10-3 18:29
Please Professor Tian Lu, is it possible to use the van der Waals surface ?

Your question does not seem very clear. Do you mean whether you can use the electrostatic potential calculated on the vdW surface as predictor of regioselectivity?

mekelleche · 发表于 Post on 2020-10-4 18:00:51

Dear wzkchem5,
yes I mean that

sobereva · 发表于 Post on 2020-10-15 06:43:58

mekelleche 发表于 2020-10-3 18:29
Please Professor Tian Lu, is it possible to use the van der Waals surface ?

The figure in #5 just corresponds to the ESP map on vdW surface.

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[波函数分析求助] How to predict the regioselectivity of an organic reaction ?

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