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Inverted Piano Stools: A Molecular Recognition Motif That Enforces 1:1 Cocrystallization of Two Diastereomers in the Same Single Crystal
Author(s) -
Brunner Henri,
Weber Matthias,
Zabel Manfred,
Zwack Thomas
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200250181
Subject(s) - diastereomer , substituent , chirality (physics) , chemistry , crystallography , molecule , hydrogen bond , solid state , single crystal , stereochemistry , crystal structure , physics , organic chemistry , chiral symmetry , quantum mechanics , nambu–jona lasinio model , quark
Half‐sandwich complexes of the type [(Ar)MXY(NR*)] (see structure; X, Y=electronegative substituents; M=Ru, Os, Rh, Ir) tend to form inversion pairs in the solid state, which are characterized by short M⋅⋅⋅M separations and CH⋅⋅⋅X/Y hydrogen bonds between the pairs of molecules. As a consequence, two diastereomers with a given chirality in the Z substituent, usually an NR* substituent, and different metal configurations approach each other with their “racemic sides” resulting in an unusually preferred 1:1 diastereomer cocrystallization in the same single crystal.