File talk:R-fluoxetine-3D-balls.png

Copy-pasted from User:DMacks' talk page on the English Wikipedia.

Stereochemistry

Seeing how you're a chemist that has a superior chemistry knowledge to me I was hoping for your help on the chirality of File:S-fluoxetine-3D-balls.png. I was wondering if the phenyl ring has a higher priority than the ethyl(methyl)amine substituent according to the CIP rules. I think it does because on the carbon directly bonded to the chiral carbon, for the phenyl group it is bonded to carbons three times (counting twice for the single double bond connected to it as part of the phenyl ring) whereas on the ethyl(methyl)amine substituent it is joined to carbon once (which is the next carbon in this chain) and hydrogen twice. I ask because if this is true one would find that this molecule is in fact right-handed i.e., (R)-fluoxetine, not (S)-fluoxetine. Brenton (contribs · email · talk · uploads) 12:11, 9 October 2014 (UTC)

(talk page stalker) The phenyl group will have a higher priority than CH₂-CH₂-NH-CH₃ and so I agree that the image is the (R)-isomer. -- Ed (Edgar181) 12:27, 9 October 2014 (UTC)

I have swapped the two images here on Commons, so they should be correct now. Ed (Edgar181) 14:40, 22 October 2014 (UTC)

D'oh! I just realized that the images were reuploaded already, so I have had to revert. Still, they should be correct now. Ed (Edgar181) 14:45, 22 October 2014 (UTC)