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Synthesis and Characterization of (–)‐Menthyl Containing N ‐Alkyl Cycloimmonium Salts
Author(s) -
Hettstedt Christina,
Betzl Wolfgang,
Karaghiosoff Konstantin
Publication year - 2012
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201100451
Subject(s) - alkyl , chemistry , substituent , pyridine , hydrogen bond , thiazole , crystal structure , van der waals force , medicinal chemistry , crystal (programming language) , van der waals radius , crystallography , stereochemistry , molecule , organic chemistry , computer science , programming language
The reaction of 4‐phenyl‐2‐aminothiazole or 2‐amino pyridine with α‐bromo acetic (–)‐menthyl ester ( 2c ) yields new N ‐alkyl cycloimmonium bromides ( 1c , 3 ) with the chiral (–)‐menthyl substituent, which were isolated and fully characterized by 1 H and 13 C NMR spectroscopy for the first time. In addition, starting from 4‐phenyl‐2‐aminothiazole, two further N ‐alkyl cycloimmonium bromides ( 1a , 1b ) were prepared. The molecular and crystal structures of all three thiazole derived N ‐alkyl cycloimmonium bromides ( 1a – c ) were determined by single‐crystal X‐ray diffraction. In all cases the crystal structures are dominated by N–H ··· Br hydrogen bonds, which results in the formation of an extensive hydrogen bonded network in the crystal. Interestingly, in all structures S ··· Br – distances shorter than the sum of the van der Waals radii are observed.