Has anyone heard of P and M notation?

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Discussion Overview

The discussion revolves around the concept of P and M notation in the context of chiral molecules, specifically focusing on biphenyl isomers with nitro and carboxylic acid groups. Participants explore the application of this notation to assign handedness to chiral structures without asymmetric carbon atoms.

Discussion Character

  • Technical explanation
  • Conceptual clarification
  • Debate/contested

Main Points Raised

  • One participant describes P and M notation as analogous to S and R designations for chiral centers, emphasizing the importance of the chiral axis and the arrangement of substituents.
  • Another participant questions whether P and M notation is part of the Kahn-Ingold-Prelog (CIP) system.
  • A different participant confirms that P and M notation is indeed covered by the CIP system, noting its application to chiral molecules lacking asymmetric atoms.
  • Participants express varying levels of familiarity with the notation and its application, indicating a learning process among them.

Areas of Agreement / Disagreement

There is some agreement that P and M notation relates to the CIP system, but the discussion includes varying interpretations and levels of understanding regarding its application to specific molecular structures.

Contextual Notes

Participants mention the need for clarity in assigning priorities and the potential complexity involved in using P and M notation, particularly in structures like biphenyl and binaphthyl.

Who May Find This Useful

This discussion may be useful for those interested in stereochemistry, particularly in understanding chiral molecules without asymmetric carbon atoms and the application of P and M notation in chemical nomenclature.

chem_tr
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Has anyone heard of P and M notation?

Hello,

A friend of mine has asked a question about a molecule, we think the molecule was a biphenyl molecule with two nitro groups on each benzo unit, along with two carboxylic acid moieties on each ring. So the molecule was shown to be in two isomers as P and M. Do you have any knowledge about P and M type isomers?

PS: We know that two phenyl units are placed perpendicular to each other.
 
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These molecules have an axis of chirality, that is, they are chiral without having any asymmetric carbon atoms. The P and M are like S and R in assigning the handedness of a chiral carbon center.

To assign one the handedness, look down the chiral axis so that the two pairs of substituents are perpendicular to one another. Assign each group a priority number, just as you would with a chirality center, but assign all of the groups in front before any of the ones in the back. Once you get used to it, you can assign the handedness now, but I often find it easier to treat the structure like it was a center of chirality. To do this, do just like you would otherwise and place the lowest priority group in the back of the structure and rotate from priority 1 to 2 to 3. Make sure you keep the priority assignments correct! M and P correspond to clockwise and anti-clockwise ordering of the groups, respectively (just like R and S).
 

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Is this part of the Kahn-Ingold-Prelog system?
 
Thank you very much. I constantly learn a great deal of knowledge from you. It is very good thing to have you here.

To tritertbutoxy: As I understood from Movies' message, it works similar to CIP system; but with one exception: This system is used in chiral molecules with no asymmetric atom. This is possible in biphenyl, binaphthyl, etc. As to the designations, I am still inexperienced, so let's just read Movies' message.
 
Last edited:
Yes, this is covered by the C-I-P system. See this paper and the references theirin: Angew. Chem., Int. Ed. Engl. 1982, 21, 567-583.

Chem_tr: It's my pleasure to help you, and others, out. The questions here cause me to learn new things!
 

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