1196-12-9Relevant articles and documents
Enthalpies of combustion of 2,2',4,4',6,6'-hexamethylazobenzene-N,N-dioxide, 2,2',6,6'-tetramethylazobenzene-N,N-dioxide, 2,4,6-trimethylnitrobenzene, and 2,6-dimethylnitrobenzene: the dissociation enthalpies of the N=N and N-O bonds
Acree, W. E.,Tucker, Sheryl A.,Pilcher, G.,Chowdhary, Afza,Silva, Maria D. M. C. Ribeiro da,Monte, M. J. S.
, p. 1253 - 1262 (1993)
The standard (po=0.1 MPa) molar enthalpies of combustion at the temperature T=298.15 K were measured by static-bomb calorimetry for crystalline 2,2',4,4',6,6'-hexamethylazobenzene-N,N-dioxide (HMABOO), 2,2',6,6'-tetramethylazobenzene-N,N-dioxide (TMABOO), 2,4,6-trimethylnitrobenzene (NITME), and liquid 2,6-dimethylnitrobenzene (NITXY).The enthalpies of sublimation at the temperature 298.15 K of HMABOO and TMABOO were assessed from vapour-pressure measurements; the enthalpy of sublimation of NITME and the enthalpy of vaporization of NITXY were measured by microcalorimetry. .The standard molar enthalpies of decomposition of the crystalline N,N-dioxides to the corresponding gaseous monomeric nitroso-compounds at T=298.15 K were measured by microcalorimetry: for HMABOO, (18.1+/-2.5) kJ*mol-1, and for TMABOO, (179.2+/-2.2) kJ*mol-1.For HMABOO and TMABOO, D(N=N)/(kJ*mol-1) was derived as (74.1+/-12.2) and (72.2+/-12.2), and /(kJ*mol-1) as (285.7+/-6.8) and (287.8+/-6.6), respectively.D(N-O)/(kJ*mol-1) in NITME and in NITXY was derived as (383.4+/-2.9) and (380.4+/-2.3), respectively.
Tungsten- and molybdenum-based coordination polymer-catalyzed N-oxidation of primary aromatic amines with aqueous hydrogen peroxide
Bordoloi, Ankur,Halligudi
, p. 2085 - 2088 (2007)
Recyclable tungsten- and molybdenum-based coordination polymers efficiently catalyzed the oxidation of primary aromatic amines to the corresponding nitroso derivatives with 30% aqueous hydrogen peroxide in high yields at room temperature.
Titania-Supported Gold Nanoparticles Catalyze the Selective Oxidation of Amines into Nitroso Compounds in the Presence of Hydrogen Peroxide
Fountoulaki, Stella,Gkizis, Petros L.,Symeonidis, Theodoros S.,Kaminioti, Eleni,Karina, Athanasia,Tamiolakis, Ioannis,Armatas, Gerasimos S.,Lykakis, Ioannis N.
supporting information, p. 1500 - 1508 (2016/05/19)
In this article, the catalytic activity of titania-supported gold nanoparticles (Au/TiO2) was studied for the selective oxidation of amines into nitroso compounds using hydrogen peroxide (H2O2). Gold nanoparticles deposited on Degussa P25 polymorphs of titania (TiO2) have been found to promote the selective formation of a variety of nitroso arenes in high yields and selectivities, even in a large-scale synthesis. In contrast, alkyl amines are oxidized to the corresponding oximes under the examined conditions. Kinetic studies indicated that aryl amines substituted with electron-donating groups are oxidized faster than the corresponding amines bearing an electron-withdrawing functionality. A Hammett-type kinetic analysis of a range of para-X-substituted aryl amines implicates an electron transfer (ET) mechanism (ρ=-1.15) for oxidation reactions with concomitant formation of the corresponding N-aryl hydroxylamine as possible intermediate. We also show that the oxidation protocol of aryl amines in the presence of 1,3-cyclohexadiene leads in excellent yields to the corresponding hetero Diels-Alder adducts between the diene and the in situ formed nitrosoarenes.
