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Zwitterionic bisulfite adducts of aldehydes: synthesis, structure, and composition of their oxidation products

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Abstract

New zwitterionic bisulfite compounds of aldehydes, such as pyridine-2-carbaldehyde (1) and qunoline-2-carbaldehydes (2), were for the first time spectroscopically characterized and structurally studied. In the crystal structures, molecules 1 and 2 are connected via intermolecular OH⋯−O3S and NH+⋯−O3S interactions to form hydrogen-bonded chains. The oxidation of a solution of 2 in dimethyl sulfoxide with atmospheric air afforded quinaldil (3) and quinaldoin (4). In the crystalline state, compound 4 exists as the enediol tautomer formed by strong intramolecular hydrogen bonds.

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Funding

The study was financially supported by the Russian Science Foundation (Project No. 22-23-01101). The X-ray diffraction analysis was performed using the equipment of the Joint Research Center of the N. S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences.

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Authors and Affiliations

  1. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russia

    A. A. Goncharenko, A. Yu. Zakharov, P. Kalle, S. I. Bezzubov & A. V. Churakov

  2. Department of Chemistry, Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russia

    A. A. Goncharenko

Authors
  1. A. A. Goncharenko
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  2. A. Yu. Zakharov
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  3. P. Kalle
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  4. S. I. Bezzubov
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  5. A. V. Churakov
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Corresponding author

Correspondence to A. V. Churakov.

Additional information

Published in Russian in Izyestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2263–2271, October, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Goncharenko, A.A., Zakharov, A.Y., Kalle, P. et al. Zwitterionic bisulfite adducts of aldehydes: synthesis, structure, and composition of their oxidation products. Russ Chem Bull 71, 2263–2271 (2022). https://doi.org/10.1007/s11172-022-3654-4

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  • DOI: https://doi.org/10.1007/s11172-022-3654-4

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