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Atropisomerism of Aromatic Carbamates
Author(s) -
Tietze Lutz F.,
Schuster Heiko J.,
von Hof J. Marian,
Hampel Sonja M.,
Colunga Juan F.,
John Michael
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001047
Subject(s) - atropisomer , chemistry , aryl , chirality (physics) , nuclear magnetic resonance spectroscopy , two dimensional nuclear magnetic resonance spectroscopy , axial chirality , crystallography , stereochemistry , organic chemistry , catalysis , physics , enantioselective synthesis , nuclear physics , chiral symmetry , alkyl , nambu–jona lasinio model , quark
ortho‐ Haloarylcarbamates like 1 – 4 show a high rotational barrier about the Naryl bond of up to 91.6 kJ mol −1 as found for 1 , which was determined by 2D exchange NMR spectroscopy (EXSY). It was further demonstrated that the height of the barrier not only depends on the substituents at the axis of chirality, but is also influenced by electronic effects.