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Condensation of 1,3‐trimethinecyanines with arylamines. Structural assignment of the products by NOE difference spectroscopy
Author(s) -
Tóth Gábor,
Bitter István,
Bigam Glen,
Strausz Ottó
Publication year - 1986
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260240208
Subject(s) - chemistry , fluorene , anthracene , nuclear overhauser effect , indene , proton , regioselectivity , condensation , two dimensional nuclear magnetic resonance spectroscopy , spectroscopy , proton nmr , condensation reaction , nuclear magnetic resonance spectroscopy , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , physics , quantum mechanics , catalysis , thermodynamics , polymer
The condensation of 1,3‐dichlorotrimethinecyanines and arylamines was found to be highly regioselective. Nuclear Overhauser effect difference experiments proved a linear structure for the formed perchlorates of 1‐aza‐9‐azonia‐1H‐benz[ f ]indene, 1‐aza‐9‐azoniaanthracene, 1,10‐diaza‐4a‐azonia‐9‐thiacyclopenta[ b ]fluorene, 6‐aza‐7‐azoniabenz[ a ]anthracene and 6,7‐diaza‐11a‐azoniabenz[ a ]anthracene derivatives. NOE difference experiments, together with 2D proton‐proton and proton‐carbon correlation measurements, allowed the complete 1 H and 13 C assignment.