Getzler Lab at KenyonCollegeDo you think cis-3-aminocyclohexanol would have a higher percent of the diaxial chair than predicted by the individual substituents due to intramolecular hydrogen bonding?
yes
no
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Nathan AckroydI voted, but am ignoring the complication of solvent effects.
@ElwoodCity we have the same instinct here, both in terms of the outcome and in terms of ignoring solvent for ease of consideration. maybe it could be considered to be in something etherial where H-bonding with solvent would be considerably less than in protic solvents or something like DMSO
If you want the equilibrium ratio, you could compare the axial destabilization from A values (+3.3 kJ/mol - I taught my synthesis class how to calculate that last week) with the stabilizing effect of the hydrogen bond (I'm sure that's in a table somewhere) to see who wins.
@ElwoodCity doing those eq values in class this week, which is what made me think of it. Should have thought of looking up H-bond energies. Wikipedia puts an NH-O at 1.9 kcal, so would be pretty considerable. Thanks thinking about it with me!
curl | sudo bashwhat phase of the chemical?
@stefani gas or liquid. Mostly considering it notionally for pedagogical purposes