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Electronic spectra and structure of 2,4-dihalopicolines and their N-oxides

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Abstract

UV spectra of 2,4-dihalopicolines and their N-oxides are presented, and the influence of substituents on spectral parameters is discussed. The electronic spectra were calculated by a modified INDO method. Transition energies, intensities, and assignments were compared with UV spectra. The degree of intramolecular charge transfer in 2,4-dihalopicolines is greater than in 2-halopicoline N-oxides and smaller than in 2-halo-4-nitropicoline N-oxides. Difference values of HOMO-LUMO energies point out that the susceptibility on photochemical reaction lies in the order: 2-halo-4-nitropicoline N-oxides > 2,4-dihalopicoline N-oxides > 2-halopicoline N-oxides > pyridine N-oxide.

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Authors
  1. Aniela Puszko
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Department of Organic Chemistry, University of Economics, PL-53-342 Wroclaw, Poland. Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 34, No. 10, pp. 1352–1366, October, 1999.

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Puszko, A. Electronic spectra and structure of 2,4-dihalopicolines and their N-oxides. Chem Heterocycl Compd 34, 1148–1160 (1998). https://doi.org/10.1007/BF02319493

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  • DOI: https://doi.org/10.1007/BF02319493

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