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Stereoselectivity in the Salt–Cocrystal Products formed by Phenylglycinol or Phenylglycine with their Respective Sodium or Hydrochloride Salts
Author(s) -
Brittain Harry G.
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22103
Subject(s) - cocrystal , chemistry , salt (chemistry) , stereoselectivity , free base , chirality (physics) , enantiomer , hydrochloride , absolute configuration , sodium , sodium salt , organic chemistry , stereochemistry , inorganic chemistry , molecule , catalysis , hydrogen bond , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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. Chirality 25:8–15, 2013 . © 2012 Wiley Periodicals, Inc.