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Basicity of Phenyl-Substituted 1,3-Oxazoles

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Abstract

Phenyl substituents in positions 2, 4, and 5 of the oxazole ring exert different effects on the electronic structure of the heteroring, which are reflected in the basicity constants of isomeric phenyl-substituted oxazoles and in changes of the spectral patterns on protonation. The calculated (AM1) gas-phase proton affinities and energies of ionization of isomeric methyl-, phenyl-, and methylphenyloxazoles were correlated with the experimental pKBH + values. In acid medium specific solvation of phenyloxazoles is possible with participation of the heterocyclic fragment.

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  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 198013, Russia

    R. E. Trifonov & V. A. Ostrovskii

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  1. R. E. Trifonov
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  2. V. A. Ostrovskii
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Trifonov, R.E., Ostrovskii, V.A. Basicity of Phenyl-Substituted 1,3-Oxazoles. Russian Journal of Organic Chemistry 37, 416–420 (2001). https://doi.org/10.1023/A:1012496827820

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