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Structural Aspects of the Enantioselectivity of Tartrates with α‐Amino‐alcohol Salts. Part II. Crystal structures of (1 R , 2 S )‐norephedrine hydrochloride and (1 R , 2 R )‐ norpseudoephedrine hydrochloride
Author(s) -
Egli Martin,
Dobler Max
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720533
Subject(s) - chemistry , monoclinic crystal system , hydrochloride , alcohol , intramolecular force , ammonium , crystal structure , group (periodic table) , stereochemistry , crystallography , medicinal chemistry , organic chemistry
Abstract Enantioselective host‐guest complexes between α‐amino‐alcohol salts and chiral tartrates can not be crystallised up to now. To study structural aspects of their enantioselectivity, crystal structures of the components were determined. Norephedrine was used as a reference guest α‐amino‐alcohol. (1 R , 2 S )‐Norephedrine hydrochloride (monoclinic, space group P 2 1 Z = 4, a = 8.455, b = 10.331, c = 12.570 Å, β = 107.45°) and (1 R , 2 R )‐norpseudoephedrine hydrochloride (monoclinic, space group P 2 1 Z = 2, a = 5.493, b = 8.052, c = 11.986 Å, β = 104.62°) both adopt M ‐synclinal conformations with respect to the ammonium and hydroxy groups. Rather short intramolecular N…O distances indicate interaction between ammonium and hydroxy groups.