Meso compound

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Lets say we have a molecule with chiral centers

---(R)---(S)--|--(S)---(R)--- The line in the middle is the plane of symmetry

Would this count as a Meso compound? Because the two S centers don't cancel out, so I reasoned that it would not be one.

Originally Posted by ebasappa

Lets say we have a molecule with chiral centers

---(R)---(S)--|--(S)---(R)--- The line in the middle is the plane of symmetry

Would this count as a Meso compound? Because the two S centers don't cancel out, so I reasoned that it would not be one.

Umm.. are the substituents on the R's and S's the same?

The two S centers have the same substituents as each other and the two R centers also mimic one another

Originally Posted by ebasappa

The two S centers have the same substituents as each other and the two R centers also mimic one another

Can you post the molecule or is this theoretical?

I'm having a hard time visualizing this just based on R's and S's lol.

Originally Posted by ebasappa

Lets say we have a molecule with chiral centers

---(R)---(S)--|--(S)---(R)--- The line in the middle is the plane of symmetry

Would this count as a Meso compound? Because the two S centers don't cancel out, so I reasoned that it would not be one.

I actually don't think so. Think about at the supposed line in the middle. The two S groups are oriented the same way. One with priorities going away from the line and one with priorities doing toward the line. You'd want them to both go toward the line (opposite configuration) to "cancel out" and be meso.

Also, in the TPR class, they explained meso compounds as "essentially am enantiomer within itself" so across the imaginary mirror line, they'd be enantiomers.

Does that make any sense? Lol.

(I could also be off.)

turn it into a fischer projection (it takes into account the chiral centers and you can determine easily from there)