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Carbon‐13 NMR investigation of the structure of hydroxy‐azoloazines with a bridgehead nitrogen
Author(s) -
Pugmire Ronald J.,
Smith James C.,
Grant David M.,
Stanovnik Branko,
Tisler Miha,
Polanc Slvenko
Publication year - 1977
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.5570140822
Subject(s) - chemistry , pyridazine , protonation , cationic polymerization , nitrogen , carbon fibers , nitrogen atom , carbon atom , sodium methoxide , chemical shift , stereochemistry , carbon 13 nmr , medicinal chemistry , organic chemistry , methanol , ring (chemistry) , ion , materials science , composite number , composite material
Carbon‐13 nmr data has been obtained on four hydroxy‐azoloazines containing a bridgehead nitrogen atom, on the corresponding methoxide derivatives, and on selected anionic and cationic derivatives. These results have been interpreted in terms of the site of protonation of the parent hydroxy‐compounds. A comparison of the anionic derivatives with those of the parent compounds demonstrate that the neutral parent hydroxy‐species exist predominately in the “hydroxy form” rather than as the ionized species. The chemical shift data also provides information on the conformation of the hydroxy‐ and methoxy‐groups in 8‐hydroxy‐6‐methyl‐ s ‐triazolo[4,3‐6]‐pyridazine and 8‐rnethoxy‐6‐methyl‐ s ‐triazolo[4,3‐ 6 ]pyridazine.