Issue 12, 1999

Synthesis, structure and metal compounds of a novel chromophoric cyanamide ligand

Abstract

The novel compound 2-cyanaminofluoren-9-one (HL) has been synthesized, and is readily deprotonated to form the corresponding cyanamide anion L. This has been isolated as the Tl+L and AsPh4+L salts. The UV/visible spectra of HL and AsPh4+L show the same amine to carbonyl charge transfer transition seen in other aminofluorenones, although at longer wavelengths. The compound AsPh4+L undergoes the reversible one electron reduction typical of fluorenones, whilst HL undergoes an irreversible reduction. The crystal structure of AsPh4+L was determined and related to the solvatochromic behaviour of the L anion. Some simple EHMO calculations have been carried out on the L anion of AsPh4+L, which show the cyanamide based HOMO and carbonyl based LUMO involved in the aforementioned CT transition. The thallium salt Tl+L has also been used as a transmetallating agent in reaction with trimethyltin chloride to produce the corresponding tin cyanamide complex [SnMe3L], and in reaction with (triphenylphosphine)gold chloride to produce the first reported gold cyanamide compound [AuL(PPh3)], whose crystal structure has been determined.

Supplementary files

Article information

Article type
Paper

J. Chem. Soc., Dalton Trans., 1999, 2059-2064

Synthesis, structure and metal compounds of a novel chromophoric cyanamide ligand

C. J. Adams, J. Chem. Soc., Dalton Trans., 1999, 2059 DOI: 10.1039/A901959F

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