Christopher J. Horan

Symmetrically H-bridged dimer of 2-carboxylatobenzenediazonium. The 1:1 complex between 2-carboxybenzenediazonium chloride and benzenediazonium-2-carboxylate

The two zwitterions in the H-bridged dimer of 2-carboxylatobenzenediazonium (1) are linked by a crystallographically symmetric O...H...O hydrogen bond with an O...O distance of 2.436 (3) A. Comparison of (1) with other benzenediazonium salts shows that the phenyl ring distortions in (1) are determined primarily by the diazonium substituent with only modest additional effects by the carboxylate group. Intramolecular neighboring group interactions between the N 2 group and the ortho COO(H) group are indicated and are discussed. The terminal N atom of the diazonium group is bent away from the neighboring carboxylato group. The N 2 and the caboxylato group are on opposite sides of the best plane of the aromatic ring

2-Carboxybenzenediazonium chloride monohydrate

C 7 H 5 N 2 O 2 + .Cl - .H 2 O, M r =202.60, mono clinic, C2/c, a=25.62 (3), b=4.964 (2), c=14.900 (14) A, β=107.15 (4) o , V=1811 (3) A 3 , Z=8, D x =1.486 g cm -3 , λ(Mo Kα)=0.71073 A, μ=3.9 cm -1 , F(000)=832, T=298 K, R=0.035 for 1275 observed reflections. The terminal N atom of the diazonium group is bent away from the carboxyl group. The N 2 and the carboxyl group are on opposite sides of the best plane of the aromatic ring and, importantly, the carboxyl group is not fully conjugated with the aromatic ring but instead is rotated [12.3 (1) o ] around the C-CO 2 axis

Potential Energy Surface and Electron Density Analysis of Phosphorus Analogues of Aromatic and Aliphatic Diazonium Ions

Abstract Potential energy surface analyses at ab initio levels including electron correlation are reported for the phosphorus analogues of diazonium ions, RXY+ with X, Y [dbnd] N, P. Protonated, methylated, and phenylated systems are compared with focus on the question regarding end-on versus edge-on coordination. Diphosphonium and phosphoazonium ions are predicted to be more stable toward dissociation than the diazonium ions. The calculated spectroscopic data may assist in their detection. Electronic density distributions of RXY+ were analyzed in a variety of ways and with a new energy decomposition method. Charge distributions are contrasted with Lewis notations. CN and CP-bonded ions show clearly distinct bonding patterns.