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Synthesis of a phenylazo‐derivative of a 1,2,3‐thiadiazolium methylide. C‐13/N‐15 NMR characterization and crystal structure analysis
Author(s) -
L'abbé Gerrit,
Frederix Ann,
Toppet Suzanne,
Declercq JeanPaul
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280252
Subject(s) - mesoionic , chemistry , crystal structure , derivative (finance) , molecule , carbon 13 nmr , stereochemistry , nuclear magnetic resonance spectroscopy , crystal (programming language) , characterization (materials science) , crystallography , medicinal chemistry , organic chemistry , nanotechnology , computer science , financial economics , programming language , economics , materials science
The N ‐phenylhydrazone derived from 4‐methoxycarbonyl‐1,2,3‐thiadiazole‐5‐carbaldehyde 6 is methylated at the N‐3 position, yielding the mesoionic compound 8 . The C‐13 and N‐15 nmr data, as well as the results from a crystal structure analysis, indicate that the molecule is best represented by the resonance forms 8A and 8B . Comparison is made with the previously synthesized thiadiazole derivative 2 which possesses thiapentalene characteristics.