Abstract
Schiff bases are a vast group of compounds characterized by the presence of a double bond linking carbon and nitrogen atoms, the versatility of which is generated in the many ways to combine a variety of alkyl or aryl substituents. Compounds of this type are both found in nature and synthesized in the laboratory. For years, Schiff bases have been greatly inspiring to many chemists and biochemists. In this article, we attempt to present a new take on this group of compounds, underlining of the importance of various types of Schiff bases. Among the different types of compounds that can be classified as Schiff bases, we chose hydrazides, dihydrazides, hydrazones and mixed derivatives such as hydrazide–hydrazones. For these compounds, we presented the elements of their structure that allow them to be classified as Schiff bases. While hydrazones are typical examples of Schiff bases, including hydrazides among them may be surprising for some. In their case, this is possible due to the amide-iminol tautomerism. The carbon–nitrogen double bond present in the iminol tautomer is a typical element found in Schiff bases. In addition to the characteristics of the structure of these selected derivatives, and sometimes their classification, we presented selected literature items which, in our opinion, represent their importance in various fields well.
Highlights
Following the recommendation of IUPAC, Schiff bases are defined as chemical compounds (imines) bearing a hydrocarbyl group on the nitrogen atom R2C = NR (R = H) (Figure 1)
The term Schiff’s base derives from the name of the German chemist Hugo Schiff, who, in 1864, was the first to describe the products resulting from the reaction of primary amines with carbonyl compounds [1].Following the recommendation of IUPAC, Schiff bases are defined as chemical compounds bearing a hydrocarbyl group on the nitrogen atom R2C = NR (R = H) (Figure 1)
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. This common feature determines the ability of Schiff bases to form complexes with transition metal ions [3,4,5,6,7]
Summary
Following the recommendation of IUPAC, Schiff bases are defined as chemical compounds (imines) bearing a hydrocarbyl group on the nitrogen atom R2C = NR (R = H) (Figure 1).
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