The other thing to remember is that at room temperature and pressure, small
sulphoxides will be able to interconvert forms from R to S rapidly. It's only
when the groups on the sulphur get big enoough (or interconnected, like in a 3
or 4 member ring) that they actually can be resolved and isolated in one
enantiopure form or another. In principle, this is also true for any other
tri-valent element with a lone pair, although I don't know if anyone has ever
done the resolution of something like 1N,2-dimethylaziridine.
Andy
On February 8, 2016 10:30:35 AM EST, Andrew Dalke <da...@dalkescientific.com>
wrote:
>Thanks Paolo and Hannes for pointing me to sulfoxide. I am enlightened!
>
>I assume this is something that every chemist knows, but it's not
>mentioned in the Daylight SMILES documentation (or the OpenSMILES
>documentation), so I had no clue. I wonder how many more cases there
>are like that.
>
>Any idea then on why the following two have inverted chiralities?
>
> >>> Chem.CanonSmiles("CN[S@@](=O)C1=CC=CC=C1")
> 'CN[S@@](=O)c1ccccc1'
>
> >>> Chem.CanonSmiles("C2.N23.[S@@]3(=O)C1=CC=CC=C1")
> 'CN[S@](=O)c1ccccc1'
>
>
>
>
> Andrew
> da...@dalkescientific.com
>
>
>
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