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Chemistry and Applications of Cyanoximes and Their Metal Complexes


Abstract. During the last three decades, considerable research effort has been dedicated to a new class of organic ligands – cyanoximes – which have the general formula NC-C(=NOH)-R, where R is an electron-withdrawing group. The presence of the CN-group makes cyanoximes ~10,000 more acidic, and better ligands than other known conventional monoximes and dioximes. Also, in numerous cases, this group provides extra nitrogen donor atoms to support the formation of bridges between metal centres in obtained coordination polymers. With 36 different R groups, the most abundant is the family of mono-cyanoximes, followed by 7 bis-cyanoximes which include aromatic and aliphatic spacers, and lately, tris-cyanoxime representing a ‘tripod’. The total number of obtained and characterized compounds is 44. These simple, low molecular weight molecules represent a series of new excellent ampolydentate ligands – ‘molecular Lego’, or building blocks – for coordination and organometallic chemistry. Un-complexed ligands, their alkali metal salts, and metal complexes, show a large spectrum of biological activity, ranging from growth regulation in plants, and antimicrobial, to a significant in vitro and in vivo cytotoxicity against human cancers. Currently, there are more than three hundred cyanoximes-based complexes, synthesized and studied using a variety of different spectroscopic methods and X-ray analysis. In this review, the preparation and stereochemistry of cyanoximes ligands, their structures and properties, as well as the most interesting coordination compounds with a broad spectrum of practical applications, are summarized.

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Publication details

The article was received on 11 Mar 2019, accepted on 15 Apr 2019 and first published on 15 Apr 2019

Article type: Perspective
DOI: 10.1039/C9DT01057B
Citation: Dalton Trans., 2019, Accepted Manuscript

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    Chemistry and Applications of Cyanoximes and Their Metal Complexes

    N. Gerasimchuk, Dalton Trans., 2019, Accepted Manuscript , DOI: 10.1039/C9DT01057B

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