title: Electronic properties of 3,3'-dimethyl-5,5'-bis(1,2,4-triazine): towards design of supramolecular arrangements of N-heterocyclic Cu(I) complexes.
abstract: A new efficient and safe synthesis of 3,3'-dimethyl-5,5'-bis-(1,2,4-triazine) is presented. The electron-density distribution and electrostatic properties (charge, electrostatic potential) of this molecule were analyzed. These properties were derived from a high-resolution single-crystal X-ray diffraction experiment at 100 K and compared to the results obtained from ab initio DFT quantum-mechanical calculations. Comparisons of its electrostatic potential features and integrated atomic charges (quantum theory of atoms in molecules, QTAIM) have been made with those of related molecules such as bipyrimidine ligands. Two methods were used to derive integrated charges: one is based on the conventional analytical procedure and the second uses a steepest-ascent numerical algorithm. Excellent agreement was obtained between these two methods. Charges and electrostatic potential were used as predictive indices of metal chelation and discussed in the light of complexation abilities of the title compound and related molecules. The crystal structure of a Cu(I) complex of 3,3'-dimethyl-5,5'-bis(1,2,4-triazine) is reported here. In the solid state, this complex forms a three-dimensional multibranch network with open channels in which counterions and solvent molecules are located. This architecture involves both cis and trans isomers of the title compound.
authors.affiliation: Ecole Centrale Paris, Laboratoire SPMS UMR CNRS 8580 1, Grande Voie des Vignes, 92295 Châtenay-Malabry, France.
authors.forename: Blandine
authors.initials: B
authors.lastname: Courcot
authors.forename: Diem Ngan
authors.initials: DN
authors.lastname: Tran
authors.forename: Bernard
authors.initials: B
authors.lastname: Fraisse
authors.forename: François
authors.initials: F
authors.lastname: Bonhomme
authors.forename: Alain
authors.initials: A
authors.lastname: Marsura
authors.forename: Nour Eddine
authors.initials: NE
authors.lastname: Ghermani
mesh_terms: D000465:Algorithms; D003300:Copper / Q000737:chemistry*; D004583:Electrons; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008024:Ligands; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry*; D011740:Pyrimidine Dimers / Q000737:chemistry; D011789:Quantum Theory; D055672:Static Electricity; D013696:Temperature; D014227:Triazines / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
chemical_list: C521667:3,3'-dimethyl-5,5'-bis(1,2,4-triazine); D006571:Heterocyclic Compounds; D008024:Ligands; D009942:Organometallic Compounds; D011740:Pyrimidine Dimers; D014227:Triazines; D003300:Copper