Bathocuproine Explained

Bathocuproine is an organic compound with the formula . It is related to [Phenanthroline|1,10-phenanthroline]] by the placement of two methyl groups and two phenyl groups in the 2,9 and 4,7 positions, respectively. Like 1,10-phenanthroline, bathocuproine is a bidentate chelating ligand. The two methyl groups flank the nitrogen centers, such that bathocuproine is a bulky ligand. It forms a monomeric 1:1 complex with nickel(II) chloride, whereas the less bulky parent phenanthroline forms a 2:1 complex.[1]

This compound was first prepared by Case and Brennan in the early 1950s [2] [3] is a pale yellow solid that is soluble in polar organic solvents.[4]

References

  1. 10.1021/ja408787k . Two-Electron HCl to H2 Photocycle Promoted by Ni(II) Polypyridyl Halide Complexes . 2013 . Powers . David C. . Anderson . Bryce L. . Nocera . Daniel G. . Journal of the American Chemical Society . 135 . 50 . 18876–18883 . 24245545 .
  2. Case . Francis H. . Brennan . James A. . Substituted 1,10-Phenanthrolines. VII. Synthesis of Certain Phenanthrolines for Use in the Detection of Cu(I) 1 . The Journal of Organic Chemistry . June 1954 . 19 . 6 . 919–922 . 10.1021/jo01371a007.
  3. Book: Diehl . Harvey . Smith . George Frederick . The Copper Reagents: Cuproine, Neocuproine, Bathocuproine. . 1972 . G. Frederick Smith Chemical Company . Columbus, Ohio . 26 . 2nd . 1 January 2023.
  4. Encyclopedia: Guosheng Liu, Yichen, Wu. 2012. Encyclopedia of Reagents for Organic Synthesis. 10.1002/047084289X.rn01392. eEROS. Bathocuproine. 978-0471936237.

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