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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M. B. Smith, J. March, March’s Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 6-th ed., John Wiley & Sons, Inc., Hoboken, New Jersey, 2007, pp. 1280–1281.
J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2-nd ed., Oxford University Press Inc., New York, 2012, p. 139.
D. P. Kjell, B. J. Slattery, M. J. Semo, J. Org. Chem., 1999, 64, 5722; DOI: https://doi.org/10.1021/jo990543v.
C. R. Pandit, N. S. Mani, Synthesis, 2009, 4032; DOI: https://doi.org/10.1055/s-0029-1217050.
M. G. Kissane, S. A. Frank, G. A. Rener, C. P. Ley, C. A. Alt, P. A. Stroud, R. K. Vaid, S. K. Boini, L. A. McKee, J. T. Vicenzi, G. A. Stephenson, Tetrahedron Lett., 2013, 54, 6587; DOI: https://doi.org/10.1016/j.tetlet.2013.09.105.
https://www.reaxys.com, Elsevier Life Sciences IP Lt4d, 2022.
A. H. Haines, D. L. Hughes, Acta Crystallogr., Section E, 2018, E74, 1314; DOI: https://doi.org/10.1107/S2056989018011556.
T. S. Cameron, W. J. Chute, Acta Crystallogr., Section B, 1979, B35, 325; DOI: https://doi.org/10.1107/S0567740879003459.
M. E. Díaz de Vivar, S. Baggio, R. Baggio, Acta Crystallogr., Section C, 2013, C69, 52, DOI: https://doi.org/10.1107/S0108270112047774.
W. Mathes, W. Sauermileh, Chem. Ber., 1951, 84, 648; DOI: https://doi.org/10.1002/cber.19510840717.
C. R. Groom, I. J. Bruno, M. P. Lightfoot, S. C. Ward, Acta Crystallogr., Section B, 2016, B72, 171; DOI: https://doi.org/10.1107/S2052520616003954.
E. Arunan, G. R. Desiraju, R. A. Klein, J. Sadlej, S. Scheiner, I. Alkorta, D. C. Clary, R. H. Crabtree, J. J. Dannenberg, P. Hobza, H. G. Kjaergaard, A. C. Legon, B. Mennucci, D. J. Nesbitt, Pure Appl. Chem., 2011, 83, 1637; DOI: https://doi.org/10.1351/PAC-REC-10-01-02.
M. A. Navasardyan, D. A. Grishanov, T. A. Tripol’skaya, L. G. Kuzmina, P. V. Prikhodchenko, A. V. Churakov, Cryst. Eng. Commun., 2018, 20, 7413; DOI: https://doi.org/10.1039/c8ce01486h.
M. A. Navasardyan, D. A. Grishanov, P. V. Prikhodchenko, A. V. Churakov, Acta Crystallogr., Section E, 2020, E76, 1331; DOI: https://doi.org/10.1107/S205698902000972X.
C. H. Görbitz, K. Prydz, S. Ugland, Acta Crystallogr., Section C, 2000, C56, e23; DOI: https://doi.org/10.1107/S0108270199016029.
D. Braghiroli, E. Mussati, M. Di Bella, M. Saladini, Tetrahedron: Asymm., 1996, 7, 831; DOI: https://doi.org/10.1016/0957-4166(96)00080-8.
S. Iwagaki, H. Kakuta, Y. Yamamura, H. Saitoh, M. Hishida, K. Fukada, K. Saito, Crystals, 2020, 10, 361; DOI: https://doi.org/10.3390/cryst10050361.
T. Ashida, S. Hirokawa, Acta Crystallogr., Section B, 1970, B26, 454; DOI: https://doi.org/10.1107/S0567740870002649.
D. R. Davies, H. M. Powell, Nature, 1951, 168, 386; DOI: https://doi.org/10.1038/168386b0.
T. Ashida, S. Hirokawa, Y. Okaya, Acta Crystallogr., 1965, 18, 122; DOI: https://doi.org/10.1107/S0365110X65000208.
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, J. Chem. Soc., Perkin Trans., 2, 1987, S1; DOI: https://doi.org/10.1039/p298700000s1.
G. M. Sheldrick, SADABS, Program for Scaling and Correction of Area Detector Data, University of Göttingen. Germany, 1997.
G. M. Sheldrick, Acta Crystallogr., Section C, 2015, C71, 3; DOI: https://doi.org/10.1107/S205322961402421.
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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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