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Topic: Stereoelectronic  (Read 3563 times)

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Offline rekhasharma

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Stereoelectronic
« on: April 22, 2010, 12:24:40 AM »
I dont understand the meaning of streoelectronic Effects in Organic Chemistry, I searched on google also, but I didnt get it. Can somebody explain with example.

Offline MissPhosgene

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Re: Stereoelectronic
« Reply #1 on: April 22, 2010, 01:04:25 AM »
Hello,

Stereoelectronic effects are a way of explaining conformations, bond geometries, and reaction outcomes based on the electronic structure of a molecule.


The anomeric effect is an example of a stereoelectronic effect. Take glucose pentaacetate for example. Using sterics as a rational to predict the conformation results in the expectation that all substituents will be equaorial, and that that will be heavily favored. However, it is found that the substituent on the anomeric  carbon carbon is favored to be axial.   

I attached a ChemDraw document because pictures are probably going to be more helpful.
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline MissPhosgene

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Re: Stereoelectronic
« Reply #2 on: April 22, 2010, 01:13:28 AM »
Oh, I forgot to say it will be helpful if you read about MO theory.
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline orgopete

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Re: Stereoelectronic
« Reply #3 on: April 22, 2010, 08:14:37 AM »
A simple stereoelectronic effect is the preference for anti elimination reactions, either cyclic or acyclic.
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