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Hydrogen bonding in phenols. VII. Synthesis and intermolecular hydrogen bonds of 2-hydroxy-2',4'-disubstituted stilbenes

E. Solčániová, Š. Kováč, and M. Rendošová

Institute of Chemistry, Komenský University, Bratislava 1

 

Abstract: The synthesis of six 2-hydroxy-2',4'-disubstituted stilbenes (2-hydroxy-2',4'-dinitrostilbene, 2-hydroxy-2'-cyano-4'-nitrostilbene? 2-hydroxy-2'-nitro-4'-aminostilbene, 2-hydroxy-2'-cyano-4'-aminostilbene, 2-hydroxy-2'-nitro-4'-isothiocyanatostilbene, 2-hydroxy-2'-cyano-4/-isothiocyanatostilbene) has been described. The infrared spectra of compounds prepared point to the existence of unusually strong intermolecular hydrogen bonds in chloroform solutions. All spectral measurements reveal that these compounds exist as "dimers" containing two hydrogen bonds in the geometrically favourable 20-membered rings. Also the infrared and ultraviolet spectra of compounds investigated are interpreted.

Full paper in Portable Document Format: 262a173.pdf

 

Chemical Papers 26 (2) 173–178 (1972)

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