title: Stereoselectivity in the salt-cocrystal products formed by phenylglycinol or phenylglycine with their respective sodium or hydrochloride salts.
abstract: The salt and stereoselective cocrystal phenomena associated with 2-phenylglycinol and 2-phenylglycine have been studied using X-ray powder diffraction and differential scanning calorimetry. The chiral identities of the free acids and their sodium salts, or the free bases and their chloride salts, were found to play a determining role as to whether a salt-cocrystal product could or could not be formed. In particular, when cocrystallization of an enantiomerically pure basic or zwitterionic substance with its enantiomerically pure acid addition salt was attempted, a salt-cocrystal was only obtained when the absolute configuration of the two reactants is opposite. On the other hand, it has been found that no stereoselectivity in salt-cocrystal formation existed in the cocrystallization of an enantiomerically pure acidic or zwitterionic substance with its enantiomerically pure base addition salt.
authors.affiliation: Center for Pharmaceutical Physics, Milford, New Jersey 08848, USA. hbrittain@centerpharmphysics.com
authors.forename: Harry G
authors.initials: HG
authors.lastname: Brittain
mesh_terms: D002152:Calorimetry, Differential Scanning; D003460:Crystallization; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D004983:Ethanolamines; C005332:N-phenylethanolamine; C008852:2-phenylglycine; D005998:Glycine