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Zur Tautomerie von 5,5‐Diphenyldihydro‐4 H ‐1,2,3‐triazol‐4‐on und 5‐Amino‐4,4‐diphenyl‐4 H ‐1,2,3‐triazolen
Author(s) -
Quast Helmut,
Hergenrüther Thomas,
Banert Klaus,
Peters Eva;Marie,
Peters Karl,
Schnering Hans Georg Von
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260117
Subject(s) - tautomer , chemistry , crystal structure , nitrogen , stereochemistry , crystallography , medicinal chemistry , organic chemistry
Tautomerism of 5,5‐Diphenyldihydro‐4 H ‐1,2,3‐triazol‐4‐one and 5‐Amino‐4,4‐diphenyl‐4 H ‐1,2,3‐triazoles Methylation of the 5‐amino‐4 H ‐1,2,3‐triazole 5 affords the N ‐methyl‐ ( 12 ) and the N , N ‐dimethylaminotriazole 13 . X‐ray diffraction analyses show that the tautomer 5b exists in the crystal and that 5b and 13 possess similar structures and atomic distances. Both compounds exhibit restricted rotation of the amino groups in solution. The comparison of UV, carbon‐13 and nitrogen‐15 spectra of the tautomeric triazoles 2 and 5 with those of the N ‐methyl compounds 3 and 13 demonstrates that the tautomers 2a and 5b are strongly favoured also in solution.