Related Experiment Video
Updated: Jun 10, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
3-Nitrophenol-4,4'-bipyridyl N,N'-dioxide (2/1): a DFT study and CSD analysis of DPNO molecular complexes
Rodolfo Moreno-Fuquen1, Jahyr Theodoro, Javier Ellena
1Departamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia. rodimo26@yahoo.es
Abstract:
The title 2:1 complex of 3-nitrophenol (MNP) and 4,4'-bipyridyl N,N'-dioxide (DPNO), 2C(6)H(5)NO(3) x C(10)H(8)N(2)O(2) or 2MNP.DPNO, crystallizes as a centrosymmetric three-component adduct with a dihedral angle of 59.40 (8) degrees between the planes of the benzene rings of MNP and DPNO (the DPNO moiety lies across a crystallographic inversion centre located at the mid-point of the C-C bond linking its aromatic rings). The complex owes its formation to O-H...O hydrogen bonds [O...O = 2.605 (3) A]. Molecules are linked by intermolecular C-H...O and C-H...N interactions forming R(2)(1)(6) and R(2)(2)(10) rings, and R(6)(6)(34) and R(4)(4)(26) macro-rings, all of which are aligned along the [1 01] direction, and R(2)(2)(10) and R(2)(1)(7) rings aligned along the [010] direction. The combination of chains of rings along the [1 01] and [010] directions generates the three-dimensional structure. A total of 27 systems containing the DNPO molecule and forming molecular complexes of an organic nature were analysed and compared with the structural characteristics of the dioxide reported here. The N-O distance [1.325 (2) A] depends not only on the interactions involving the O atom at the N-O group, but also on the structural ordering and additional three-dimensional interactions in the crystal structure. A density functional theory (DFT) optimized structure at the B3LYP/6-311G(d,p) level is compared with the molecular structure in the solid state.
More Related Videos
Related Concept Videos
Valence Bond Theory
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Crystal Field Theory - Tetrahedral and Square Planar Complexes
Crystal field theory (CFT) is applicable to molecules in geometries other than octahedral. In octahedral complexes, the lobes of the dx2−y2 and dz2 orbitals point directly at the ligands. For tetrahedral complexes, the d orbitals remain in place, but with only four ligands located between the axes. None of the orbitals points directly at the tetrahedral ligands. However, the dx2−y2 and dz2 orbitals (along the Cartesian axes) overlap with the ligands less than the dxy,...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Diazonium Group Substitution: –OH and –H
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

