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Polarity and Conformational Analysis of Tri(1-naphthyl)phosphine, Tri(2-naphthyl)phosphine, and Their Chalcogenides

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Abstract

The polarity and structure of tri(1- or 2-naphthyl)phosphines and their chalcogenides were determined by the methods of dipole moments, IR spectroscopy, and DFT quantum-chemical calculations at the B3PW91/6-311++G(df,p) level of theory. In solution, tri(1-naphthyl)phosphine prefers a single conformer with a gauche,gauche,gauche orientation of the substituents at the phosphorus. Tri(2-naphthyl)phosphine, as well as both phosphine chalcogenides exist as equilibrium mixtures of several forms with a propeller arrangement of the substituents and a cis or gauche orientation of the Csp2‒Csp2 and P=X (X = LEP, O, S, Se) bonds.

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 20-03-00119).

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Authors and Affiliations

  1. Kazan (Volga Region) Federal University, 420008, Kazan, Russia

    A. A. Kuznetsova & Ya. A. Vereshchagina

  2. Kazan Department of Joint Supercomputer Center of Russian Academy of Sciences – Branch of Federal State Institution “Scientific Research Institute for System Analysis of the RAS”, 420111, Kazan, Russia

    D. V. Chachkov

  3. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    N. A. Belogorlova, V. A. Kuimov & S. F. Malysheva

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  1. A. A. Kuznetsova
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  2. D. V. Chachkov
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  3. N. A. Belogorlova
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  4. V. A. Kuimov
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  5. S. F. Malysheva
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  6. Ya. A. Vereshchagina
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Correspondence to Ya. A. Vereshchagina.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 8, pp. 1120–1131 https://doi.org/10.31857/S0514749221080036.

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Kuznetsova, A.A., Chachkov, D.V., Belogorlova, N.A. et al. Polarity and Conformational Analysis of Tri(1-naphthyl)phosphine, Tri(2-naphthyl)phosphine, and Their Chalcogenides. Russ J Org Chem 57, 1245–1255 (2021). https://doi.org/10.1134/S1070428021080030

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  • DOI: https://doi.org/10.1134/S1070428021080030

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