Pioneered by other researchers in the 1980s, SIMPLE (Secondary Isotopic Multiplets of Partially Labeled Entities) NMR, uses deuterium isotope effects, observable in the ¹H-NMR spectra of partially deuterated molecules to detect intramolecular hydrogen bonds. We have studied how this method can be used to detect hydrogen bonding in 1,6 diols such as epoxyquinol A dimer 5 from the lab of Professor John Porco (Boston University) and a novel BAMOL catalyst from the lab of Professor Viresh Rawal (University of Chicago), which employs hydrogen bonding to facilitate asymmetric hetero-Diels Alder reactions. We also synthesized a series of 1,6 diol model systems to study with this method. Implementation of SIMPLE NMR on these 1,6 diols showed large isotope shifts (ca. 16-30 ppb), indicating that there is some degree of intramolecular hydrogen bonding in these compounds. These results are promising and open the door for further SIMPLE NMR applications to other 1,6 diols.

epoxyquinol A dimer 5                        BAMOL 7                           1,6 diol 11