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Solid-State and Solution Structural Studies of 4-{[C(E)]-1H-Azol-1-ylimino)methyl}pyridin-3-ols

✍ Scribed by Dionisia Sanz; Almudena Perona; Rosa M. Claramunt; Elena Pinilla; M. Rosario Torres; José Elguero

Book ID
102253411
Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
173 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

The new N-salicylideneheteroarenamines 1 -4 were prepared by reacting the biologically relevant 3hydroxy-4-pyridinecarboxaldehyde (5) with 1H-imidazol-1-amine (6), 1H-pyrazol-1-amine ( 7), 1H-1,2,4triazol-1-amine ( 8), and 1H-1,3,4-triazol-1-amine (9). Solution 1 H-, 13 C-, and 15 N-NMR were used to establish that the hydroxyimino form A is the predominant tautomer. A combination of 13 C-and 15 N-CPMAS-NMR with X-ray crystallographic studies confirms that the same form is present in the solid state. The stabilities and H-bond geometries of the different forms, tautomers and rotamers, are discussed by using B3LYP/6-31G** calculations.

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