Conformational Analysis of 2-Substituted Alkylphosphoryl Compounds. 4. Substituent Effect on the Nature of the Hydrogen Bonding in (2-Hydroxyalkyl)phosphoryl Systems.

The extent to which solid state conformational and hydrogen bonding preferences of five (2-hydroxyalkyl)phosphoryl compounds 2a-e [R(1)(2)P(O)CH(2)CH(OH)R(2); 2a, R(1) = MeO, R(2) = Ph; 2b, R(1) = R(2) = Ph; 2c, R(1) = Ph, R(2) = Bu(t); 2d, R(1) = Me, R(2) = Ph; 2e, R(1) = Me, R(2) = Bu(t)] change upon dissolution has been investigated using X-ray crystallography, IR, and NMR spectroscopy. Intermolecular hydrogen bonding involving inversion-center-related cyclic dimers is shown to be a common solid state arrangement, with relatively small structural changes producing infinite chains. Intramolecular hydrogen bonded monomers are uncommon.