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New basicity/nucleophilicity scale on the basis of parameters of formation of axial n,ν-complexes derived from tetraphenylporphyrinatozinc(II) and base/nucleophile as ligand

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Abstract

The stability constants of complexes derived from tetraphenylporphyrinatozinc(II) and various ligands in chloroform at 25°C were proposed as nucleophilicity/basicity parameters of the latter, which reflect the effects of electronic and steric factors. Supernucleophilicity of heteroaromatic N-oxides in reactions with electrophiles was interpreted in terms of sp 2–sp 3 rehybridization of the N-oxide oxygen atom.

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Authors and Affiliations

  1. Petrozavodsk State University, pr. Lenina 33, Petrozavodsk, 185910, Russia

    V. P. Andreev & Ya. P. Nizhnik

  2. Institute of Solution Chemistry, Russian Academy of Sciences, Ivanovo, Russia

    N. Sh. Lebedeva

Authors
  1. V. P. Andreev
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  2. Ya. P. Nizhnik
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  3. N. Sh. Lebedeva
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Correspondence to V. P. Andreev.

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Original Russian Text © V.P. Andreev, Ya.P. Nizhnik, N.Sh. Lebedeva, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 6, pp. 914–922.

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Andreev, V.P., Nizhnik, Y.P. & Lebedeva, N.S. New basicity/nucleophilicity scale on the basis of parameters of formation of axial n,ν-complexes derived from tetraphenylporphyrinatozinc(II) and base/nucleophile as ligand. Russ J Org Chem 44, 906–915 (2008). https://doi.org/10.1134/S1070428008060213

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  • DOI: https://doi.org/10.1134/S1070428008060213

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