Substituent effects in the polarography of aromatic diazonium salts

p-Diethylaminobenzenediazonium hexafluorophosphate, C10H14N3+•PF6−, crystallized in space group [Formula: see text] with a = 12.105(4), b = 12.340(5), c = 10.439(4) Å, α = 96.53(3), β = 104.11(3), γ = 64.44(3)°, and Z = 4. The structure was solved using direct methods and refined with full-matrix least-squares techniques on F, to a final R of 0.054 for 1917 reflections with F2 > 3σ(F2). The mean bond lengths for the diazo group are: N—N 1.096(6); C—N 1.357(7) Å. The geometry of the molecule is discussed in terms of the possible resonance forms and it is shown to be consistent with a form in which the N—N triple bond is essentially intact and the aminobenzene moiety has "quinoidal" character.

Section: Methodssupporting

confidence: 79%

The crystal structure of p-diethylaminobenzenediazonium hexafluorophosphate

Ball¹,

Elofson²

1985

“…quencies (5) and redox properties (6) have continued to use o+ constants rather than oP constants to 1 obtain good results. These procedures suggested that contributions from the form 2 were important to describe the properties of these compounds.…”

Section: Introductionmentioning

confidence: 99%

The crystal structure of benzenediazonium tetrafluoroborate, C₆H₅N₂⁺•BF₄⁻¹

Cygler¹,

Przybylska²,

Elofson³

1982

MIROSLAW CYCLER, MARIA PRZYBYLSKA, and RICHARD MACLEOD ELOFSON. Can. J . Chem. 60, 2852Chem. 60, (1982. Benzenediazonium tetrafluoroborate, C6HsN2+.BF,-, crystallizes in space group P2, In with unit cell dimensions n = 17.347(2), b = 8.396(1), c = 5.685(1) A, P = 92.14(1)", Z = 4. The structure was solved by direct phasing methods using the program SHELX 76.The parameters were refined by full-matrix least-squares to a final R = 0.063 for 1346 observed reflections. The bond lengths and angles agree very well with those of Rplmming for benzenediazonium chloride. The C-N and N=N bond lengths are 1.415(3) and 1.083(3) A, respectively, and the bonds of the benzene ring do not show any significant differences as they vary from 1.371 (5)

“…Experimental conditions were those previously described (1). However, a new polarograph (Princeton Applied Research Model 170) operating in the three electrode configuration was used.…”

Section: Methodsmentioning

confidence: 99%

“…In 1969, we reported the results of our work on the effect of substituents on the half-wave reduction potentials of aryl diazonium tetrafluoroborates in the aprotic solvent sulfolane (1). These results produced a good Hammett plot [l].…”

Section: Introductionmentioning

confidence: 99%

Polarographic redox potentials of diazotized polycyclic aromatic amines and the absolute electrode potentials

Elofson¹,

Gadallah²,

Schulz³

et al. 1984

Self Cite

Can. J. Chem. 62,1772(1984. The half-wave potentials (El/z) of polycyclic diazonium salts as well as those of the parent hydrocarbons, the corresponding aldehydes, and the nitro compounds, when plotted against the coefficient of the energy of either the lowest vacant orbital [Traduit par le journa(] Introduction In 1969, we reported the results of our work on the effect of substituents on the half-wave reduction potentials of aryl diazonium tetrafluoroborates in the aprotic solvent sulfolane (1). These results produced a good Hammett plot [l]. Only one reversible, one electron-reduction wave was observed.