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
>
>
>
>------------------------------------------------------------------------------
>Site24x7 APM Insight: Get Deep Visibility into Application Performance
>APM + Mobile APM + RUM: Monitor 3 App instances at just $35/Month
>Monitor end-to-end web transactions and take corrective actions now
>Troubleshoot faster and improve end-user experience. Signup Now!
>http://pubads.g.doubleclick.net/gampad/clk?id=272487151&iu=/4140
>_______________________________________________
>Rdkit-discuss mailing list
>Rdkit-discuss@lists.sourceforge.net
>https://lists.sourceforge.net/lists/listinfo/rdkit-discuss
--
Sent from my Android device with K-9 Mail. Please excuse my brevity.
------------------------------------------------------------------------------
Site24x7 APM Insight: Get Deep Visibility into Application Performance
APM + Mobile APM + RUM: Monitor 3 App instances at just $35/Month
Monitor end-to-end web transactions and take corrective actions now
Troubleshoot faster and improve end-user experience. Signup Now!
http://pubads.g.doubleclick.net/gampad/clk?id=272487151&iu=/4140
_______________________________________________
Rdkit-discuss mailing list
Rdkit-discuss@lists.sourceforge.net
https://lists.sourceforge.net/lists/listinfo/rdkit-discuss