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

• Published in: Russian chemical bulletin Vol. 71; no. 10; pp. 2263 - 2271
• Main Authors: Goncharenko, A. A., Zakharov, A. Yu, Kalle, P., Bezzubov, S. I., Churakov, A. V.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-10-2022; Springer Nature B.V
• Subjects: Adducts; Aldehydes; Bonding strength; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Dimethyl sulfoxide; Full Articles; Hydrogen bonding; Hydrogen bonds; Inorganic Chemistry; Organic Chemistry; Oxidation; Tautomers; Zwitterions; bisulfite compounds; crystal structure; zwitterions; hydrogen bonds; oxidation of aldehydes
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-022-3654-4

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⋯−O
3
S and NH
+
⋯−O
3
S 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.