[critzz]

Regardless whether this compound could exist or not, would it be chiral?

[discodermolide]

What are the criteria used to determine if a molecule is chiral or not?

[critzz]

That it's asymmetric. However, normally you can determine it very easily if there is a chiral carbon (when it has 4 different groups attached).
In this case the nitrogen is chiral, where the 4th group is a lone pair of electrons?

[AWK]

This compound has two asymmetric atoms.

[Burner]

That it's asymmetric. However, normally you can determine it very easily if there is a chiral carbon (when it has 4 different groups attached).

There is a chiral carbon atom in this structure.

[critzz]

Ah of course also the carbon at the back side... stupid of me  .

Maybe this is a better example of what I mean:



So it's still chiral because the electron pairs of the nitrogen are fixed and can't scramble?
Then, would for example N-ethyl-N-methyl-propylamine be chiral at really low temperatures?

[Dan]

So it's still chiral because the electron pairs of the nitrogen are fixed and can't scramble?

You need to go back to the definition. Chirality is a property of a whole molecule, not a single atom. The presence of "chiral" centres does not necessarily confer chirality to the molecule (e.g. ribitol, galactitol etc. meso compounds in general). For this reason, I prefer the term "asymmetric centre" to "chiral centre".

A molecule is chiral if it has a non-superimposable mirror image. Draw the mirror image of your compound, are they superimposable?

A short cut is to look for a plane or centre of symmetry - if either of these are present, the molecule is achiral. Can you see any planes of symmetry in your molecule?

[critzz]

Ugh, you are right, it possesses simple Cs-symmetry.

Last try then.



The nitrogen in the front would be (R)-configuration and the nitrogen in the back (S)-configuration?

[Dan]

The nitrogen in the front would be (R)-configuration and the nitrogen in the back (S)-configuration?

Yes, I think so.