Bathocuproine is an organic compound with the formula . It is related to
1,10-phenanthroline by the placement of two
methyl group
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...
s and two
phenyl group
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...
s in the 2,9 and 4,7 positions, respectively. Like 1,10-phenanthroline, bathocuproine is a
bidentate chelating
Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...
ligand
In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...
. 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.
This compound was first prepared by Case and Brennan in the early 1950s is a pale yellow solid that is soluble in polar organic solvents.
[{{cite encyclopedia, author=Guosheng Liu, Yichen, Wu, year=2012, title = Encyclopedia of Reagents for Organic Synthesis, doi=10.1002/047084289X.rn01392, encyclopedia=eEROS, chapter=Bathocuproine, isbn=978-0471936237]
References
Chelating agents
Phenanthrolines