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Direct assignment of the absolute configuration of molecules from crystal morphology
Author(s) -
Weissbuch Isabelle,
Leiserowitz Leslie,
Lahav Meir
Publication year - 2008
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.20498
Subject(s) - absolute configuration , chemistry , molecule , dissolution , crystal (programming language) , crystallography , solvent , polar , crystal structure , absolute (philosophy) , chemical polarity , stereochemistry , organic chemistry , physics , astronomy , computer science , programming language , philosophy , epistemology
A method for direct assignment of the absolute configuration of molecules and the absolute structures of polar crystals, independent to that of Bijvoet, is described. The method correlates between the two‐dimensional packing arrangement of specific faces, that delineate crystals during their growth and dissolution, with molecules present in the environment. The structural information stored in these faces is transferred to “tailor‐made” molecules added to the solvent by controlled morphological changes induced to the growing crystals and by the creation of etch pits at specific crystal faces during their dissolution. In addition, the “tailor‐made” molecules are occluded enantioselectively as guests within specific sectors of the host crystals. The method is illustrated for a variety of molecules and crystals including the assignment of the absolute configuration of several α‐amino acids as “tailor‐made” additives in centrosymmetric crystals of glycine and serine, for the absolute structure of polar crystals of sugars and α‐amino acids and consequently the absolute configuration of molecules packed in such crystals. Chirality, 2008. © 2008 Wiley‐Liss, Inc.