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Chemistry of the phenoxathiins and isosterically related heterocycles. XVIII . The synthesis, 1 H‐ and 13 C‐NMR Spectroscopy of benzo[ b ]‐1,4,9‐triazaphenoxathiin
Author(s) -
Turley James C.,
Martin Gary E.,
Inners Ruth R.
Publication year - 1981
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.5570180622
Subject(s) - chemistry , chemical shift , nuclear magnetic resonance spectroscopy , carbon 13 nmr satellite , molecule , coupling constant , nmr spectra database , stereochemistry , resonance (particle physics) , relaxation (psychology) , fluorine 19 nmr , crystallography , spectral line , organic chemistry , psychology , social psychology , physics , particle physics , astronomy
The first synthesis of a triazaphenoxathiin system, benzo[ b ]‐1,4,9‐triazaphenoxathiin, is reported. Attempts directed toward the total assignment of the 13 C‐nmr spectrum of the title compound failed to produce an unequivocal assignment. The carbons of the benzo‐portion of the molecule could not be unequivocally assigned at 25.2 MHz but were subgrouped into permutable pairs of resonances on the basis of relaxation times, a result of the antisotropic reorientation of the molecule. Further attempts to complete the 13 C‐nmr assignment at 100 MHz by selective on‐resonance decouplings in the 400 MHz 1 H‐nmr spectrum were also unsuccessful because of similarities in the chemical shifts of the benzo‐protons. Complete 1 H‐nmr chemical shifts and homo‐nuclear spin‐coupling constants were obtained using the PANIC program.