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Basicity of azoles: complexes of diiodine with imidazoles, pyrazoles and triazoles

✍ Scribed by M. J. El Ghomari; R. Mokhlisse; C. Laurence; J.-Y. Le Questel; M. Berthelot

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
123 KB
Volume
10
Category
Article
ISSN
0894-3230

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✦ Synopsis

The diiodine basicity (a soft Lewis basicity) of 15 azoles (imidazoles, pyrazoles and triazoles) was measured by means of the formation constant of the diiodine-azole complexes in heptane at 298 K. The preferred sites of diiodine fixation are the nitrogens N-3 in imidazoles, N-2 in pyrazoles and N-4 in 1,2,4-triazoles. The diiodine basicity decreases with (i) the number of ring nitrogens, (ii) benzofusion, (iii) field electron-withdrawing effects of substituents on N-1 and (iv) for pyrazoles only, steric effect of substituents on N-1. In imidazoles and 1,2,4-triazoles, the lengthening and branching of alkyl groups on N-1 increase significantly the basicity, and 1-(adamant-1-yl)imidazole is the most basic of the azoles studied.

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