title: Cu(NO3)2.3H2O-mediated synthesis of 4'-(2-pyridyl)-2,2':6',2' '-terpyridine (L2) from N-(2-pyridylmethyl)pyridine-2-methylketimine (L1). A C-C bond-forming reaction and the structure of {[Cu(L2)(OH)(NO3)][Cu(L2)(NO3)2]}.2H2O.
abstract: N-(2-Pyridylmethyl)pyridine-2-methylketimine (L1) was synthesized from equimolar quantities of (2-pyridyl)methylamine and 2-acetylpyridine. Methanolic solution of L1 reacted readily with Cu(NO3)2.3H2O in air, affording green solid of composition {[Cu(L2)(OH)(NO3)][Cu(L2)(NO3)2]}.2H2O, where L2 is 4'-(2-pyridyl)-2,2':6',2' '-terpyridine. Oxidation of the active methylene group of L1 to an imide and then condensation with 2-acetylpyridine involving a C-C bond-forming reaction, mediated by a Cu2+ ion, are the essential steps involved in the conversion of L1 to L2. L2 is isolated by extrusion of Cu2+ with EDTA(2-). The copper center in [Cu(L2)(OH)(NO3)] has a mer-N3O3 environment, and that in [Cu(L2)(NO3)2] has a distorted trigonal-bipyramidal geometry. Two H2O molecules held by C-H...O interactions are present in the predominantly hydrophobic channels of approximate cavity dimension 7.60 x 6.50 A created by aromatic rings through pi-pi interactions.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati 781 039, Assam, India.
authors.forename: Sumanta Kumar
authors.initials: SK
authors.lastname: Padhi
authors.forename: Vadivelu
authors.initials: V
authors.lastname: Manivannan
mesh_terms: D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009566:Nitrates / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009566:Nitrates; D009942:Organometallic Compounds; D011725:Pyridines; D003300:Copper; C516433:copper(II) nitrate