H-bond competition experiments in solution and the solid state

The H-bonding outcomes in crystal structures of simple molecules, where two potential H-bonds can be formed, have been used to calculate relative H-bond probabilities for 59 combinations of H-bond donors and H-bond acceptors. H-bond probabilities are shown to correlate well with the difference in solution phase free energy between the two competing H-bonds. When two different H-bond acceptors compete for a single H-bond donor, the outcomes in crystal structures of simple molecules are consistent with the results of solution phase measurements in non-polar solvents.