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Synthesis of Triarylantimony(V) Compounds with Salicylic and Acetylsalicylic Acids

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Abstract

The reactions of triarylantimony with t-BuOOH and salicylic/acetylsalicylic acids (1 : 1 : 2) afforded triarylantimony(V) derivatives: pTol3Sb(O2CC6H4-2-OH)2 (80% yield), Ph3Sb(O2CC6H4-2-OH)2 (38%), Ph3Sb(O2CC6H4-2-OAc)2 (82%), (Ph3SbO2CC6H42OH)2O (39%). The structures of the obtained compounds were compared using the structural parameter τ (X-ray diffraction data) and the differences between νas(COO) and νs(COO) (IR spectroscopy data). For all the synthesized compounds, the antimony atom was found to have intermediate coordination between trigonal bipyramidal and tetragonal pyramidal and to be additionally coordinated to the carbonyl oxygen atoms. The obtained triarylantimony disalicylates at room temperature react quantitatively with aqueous solution of NaOH by means of the salicylate groups elimination. Under similar conditions, Ph3Sb(O2CC6H4-2-OAc)2 eliminates acetylsalicylate groups, which undergo further hydrolysis to salicylate groups.

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ACKNOWLEDGMENTS

Authors are grateful to Yu.B. Malysheva (Lobachevsky State University of Nizhny Novgorod) for recording NMR spectra. The study was carried out on the equipment of the Collective Usage Center “New Materials and Resource-Saving Technologies” of the Lobachevsky State University of Nizhny Novgorod.

Funding

This study was financially supported by the Ministry of Education and Science of the Russian Federation within the framework of the basic part of the state assignment (project FSWR-2023-0025).

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Authors and Affiliations

  1. Lobachevsky State University of Nizhny Novgorod, 603022, Nizhny Novgorod, Russia

    A. V. Gushchin, N. V. Sokolova, V. V. Levina, V. R. Vakhitov, M. A. Giricheva, N. S. Kuzmina & N. V. Somov

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  1. A. V. Gushchin
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  2. N. V. Sokolova
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  3. V. V. Levina
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  4. V. R. Vakhitov
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  5. M. A. Giricheva
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  6. N. S. Kuzmina
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  7. N. V. Somov
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Correspondence to A. V. Gushchin.

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To the 35th Anniversary of the founding of the G.A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences

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Gushchin, A.V., Sokolova, N.V., Levina, V.V. et al. Synthesis of Triarylantimony(V) Compounds with Salicylic and Acetylsalicylic Acids. Russ J Gen Chem 93 (Suppl 3), S805–S813 (2023). https://doi.org/10.1134/S1070363223160193

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