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■ Extensive Hydrate Formation of 5-Nitrofurfural in Neutral Aqueous Solutions: Implications for Its Reactivity

Ruud W. Busker, Gerard M. J. Beijersbergen van Henegouwen, and Kees Erkelens

*Division of Medicinal Chemistry, Center for Bio-Pharmaceutical Science, Gorlaeus Laboratories, Leiden University, P.O.Box 9502, Einsteinweg 55, 2300 RA Leiden, The Netherlands

Abstract

In neutral aqueous solutions up to 56% of nitrofurfural was found to be in the geminal diol form. This was concluded from NMR experiments with nitrofurfural in DNSO-d₆ with increasing amounts of D₂0 In DMSO nitrofurfural reacts faster with hydrazine than p-nitrobenzaldehyde does; in water the reverse holds. The decreased reactivity of nitrofurfural in water is caused by the large extent of hydration.