Pyridine → 2,2'-Bipyridine

Participants

Reaction Steps

A suspension of CeBr3(THF)4 (complex 2) (0.050 grams, 0.075 millimoles) in dichloromethane (10 milliliters) was prepared. A solution of bipyridine (0.023 grams, 0.150 millimoles) in dichloromethane was prepared and added to the suspension. After allowing the resulting yellow suspension to continue stirring overnight, the reaction mixture was allowed to settle. The solvent was decanted. The yellow solid was washed twice with cold dichloromethane to remove unreacted bipyridine. The solid was dried in vacuo, affording a bright yellow solid. A saturated solution of the yellow solid in pyridine was prepared. Slow diffusion of hexanes into the saturated solution produced yellow block-shaped crystals of CeBr3(bipyridine)(pyridine)3 (complex 6) that proved to be suitable for X-ray diffraction. The crystals were washed with cold toluene and dried under argon. Yield: 0.035 grams, 62%). The FT-IR spectrum included peaks at 1600 and 1441 cm−1 assigned to pyridine C═C and C═N stretches (compared to 1541 and 1439 cm−1, respectively, for neat pyridine), and peaks at 1595 and 1436 cm−1 assigned to C═C and C═N stretches for bipyridine. Analysis calculated for C25H23N3CeBr3: C (38.83%), H (3.00%), N (9.06%). Found: C (37.71%), H (2.81%), N (8.58%). An ORTEP representation of 6 is shown in FIG. 4. Hydrogen atoms were omitted for clarity.

Provenance & Evidence