TY - JOUR
T1 - Molecular recognition on crystallization of enantiopure and racemic N-benzoylalanine methyl ester
AU - Coghlan, Daniel R.
AU - Easton, Christopher J.
AU - Tiekink, Edward R.T.
PY - 2000
Y1 - 2000
N2 - The melting points of crystals of (S)- and (RS)-N-benzoylalanine methyl ester derived from solutions of ethyl acetate/light petroleum are 56-57.5° and 81.5-82.5°, respectively, reflecting differences in lattice energy that are apparent from the crystal structures. A more extensive mode of association between chains, uniformly stabilized by N-H⋯O=C interactions, is found in the racemate leading to a more efficient packing of molecules. The higher lattice energy of the racemate has been confirmed through the enantiomeric enrichment of an optically active sample and the partial resolution of (RS)-N-benzoyl(2-2H)alanine methyl ester, through molecular recognition on crystallization.
AB - The melting points of crystals of (S)- and (RS)-N-benzoylalanine methyl ester derived from solutions of ethyl acetate/light petroleum are 56-57.5° and 81.5-82.5°, respectively, reflecting differences in lattice energy that are apparent from the crystal structures. A more extensive mode of association between chains, uniformly stabilized by N-H⋯O=C interactions, is found in the racemate leading to a more efficient packing of molecules. The higher lattice energy of the racemate has been confirmed through the enantiomeric enrichment of an optically active sample and the partial resolution of (RS)-N-benzoyl(2-2H)alanine methyl ester, through molecular recognition on crystallization.
KW - Amino acid methyl ester
KW - Deuterium substitution
KW - Enantiomeric enrichment
KW - Supramolecular chemistry
KW - X-ray crystal structure
UR - http://www.scopus.com/inward/record.url?scp=18744383941&partnerID=8YFLogxK
U2 - 10.1071/ch00084
DO - 10.1071/ch00084
M3 - Article
SN - 0004-9425
VL - 53
SP - 551
EP - 556
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 7
ER -