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Neocuproine
|Section2= }} Neocuproine is a heterocyclic organic compound and chelating agent. Phenanthroline ligands were first published in the late 19th century, and the derivatives substituted at the 2 and 9 positions are among the most studied of the modified phenanthrolines. ==Synthesis and structure== Neocuproine can be prepared by sequential Skraup reactions (Doebner-Miller reaction/condensation) of o-nitroaniline (2-Nitroaniline) with crotonaldehyde diacetate: :File:Recipe 2.gif An alternate synthesis involves the condensation of o-phenylenediamine, m-nitrobenzenesulphonate, and crotonaldehyde diacetate. This method gives higher yields but is less economical. Neocuproine crystallizes as a dihydrate and a hemihydrate as well as a hydrated hydrochloride salt. The structure of the dihydrate features a π-stacking motif, with additional hydrogen bonding between the basic nitrogen centers and water.〔Koroglu, Ahmet; Bulut, Ahmet; Ucar, Ibrahim; Nichol, Gary; Harrington, Ross W.; Clegg, William "A second monoclinic polymorph of 2,9-dimethyl-1,10-phenanthroline dihydrate" ''Organic Papers'', E61, 2005, p.3723-3725. 〕
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