100667-92-3

Upstream product

• 1008-88-4 3-phenylpyridine 
• 94707-38-7 10-methyl-9-phenylacridinium trifluoromethanesulphonate 
• 602-56-2 9-phenylacridine 
• 75-64-9 tert-butylamine 
• 5464-91-5 10-methyl-9-phenylacridin-10-ium chloride 
• 42206-02-0 N-methyl-9-phenylacridinium cation 
• 100-46-9 benzylamine 
• 108-99-6 3-Methylpyridine 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 626-61-9 4-Chloropyridine 
• 109-09-1 2-chloropyridine 
• 626-60-8 3-Chloropyridine 
• 372-47-4 3-Fluoropyridine 
• 108-48-5 2,6-dimethylpyridine 

Relevant academic research and scientific papers

Hydride transfer from 9-substituted 10-methyl-9,10-dihydroacridines to hydride acceptors via charge-transfer complexes and sequential electron- proton-electron transfer. A negative temperature dependence of the rates

The reactivity of 9-substituted 10-methyl-9,10-dihydroacridine (AcrHR) in the reactions with hydride acceptors (A) such as p-benzoquinone derivatives and tetracyanoethylene (TCNE) in acetonitrile varies significantly spanning a range of 107 starting from R = H to Bu(t) and CMe2COOMe. Comparison of the large variation in the reactivity of the hydride transfer reaction with that of the deprotonation of the radical cation (AcrHR·+) determined independently indicates that the large variation in the reactivity is attributed mainly to that of proton transfer from AcrHR·+ to A·- following the initial electron transfer from AcrHR to A. The overall hydride transfer reaction from AcrHR to A therefore proceeds via sequential electron-proton-electron transfer in which the initial electron transfer to give the radical ion pair (AcrHR·+ A·-) is in equilibrium and the proton transfer from AcrHR·+ to A·- is the rate- determining step. Charge-transfer complexes are shown to be formed in the course of the hydride transfer reactions from AcrHR to p-benzoquinone derivatives. A negative temperature dependence was observed for the rates of hydride transfer reactions from AcrHR (R = H, Me, and CH2Ph) to 2,3- dichloro-5,6-dicyano-p-benzoquinone (DDQ) in chloroform (the lower the temperature, the faster the rate) to afford the negative activation enthalpy (ΔH((+))(obs) = -32, -4, and -13 kJ mol-1, respectively). Such a negative ΔH((+))(obs) value indicates clearly that the CT complex lies along the reaction pathway of the hydride transfer reaction via sequential electron- proton-electron transfer and does not enter merely through a side reaction that is indifferent to the hydride transfer reaction. The ΔH((+))(obs) value increases with increasing solvent polarity from a negative value (-13 kJ mol-1) in chloroform to a positive value (13 kJ mol-1) in benzonitrile as the proton-transfer rate from AcrHR·+ to DDQ·- may be slower.

Photoalkylation of 10-alkylacridinium ion via a charge-shift type of photoinduced electron transfer controlled by solvent polarity

A charge-shift type of photoinduced electron-transfer reactions from various electron donors to the singlet excited state of 10-decylacridinium cation (DeAcrH+) in a nonpolar solvent (benzene) is found to be as efficient as those of 10-methylac

Nucleophilic addition versus electron transfer in carbonylmetallate salts. Donor-acceptor interactions in the precursor ion pairs

The isostructural pentacarbonylmetallate anions M(CO)-5 (M=Mn and Re) react with a series of N-methylpyridinium cations (Py+) to yield products of nucleophilic addition [NA=Py-M(CO)5] or of one-electron redox re

Steric and kinetic isotope effects in the deprotonation of cation radicals of NADH synthetic analogues

The deprotonation rate constants and kinetic isotope effects of the cation radicals have been determined by combined use of direct electrochemical techniques at micro- and ultramicroelectrodes, redox catalysis, and laser flash photolysis, over a extended

Photoreduction of Methyleneblue by the Two-Equivalent Electron Donor N-Methyl-9-phenylacridane and the Use of the System for the Spectrally Sensitized Dediazoniation of p-N,N-Dimethylamino Benzenediazonium Tetrafluoroborate

The photoreduction of methyleneblue by N-methyl-9-phenylacridane (ACH) is studied in acetonitrile by means of flash photolysis and quantum yields.In the first step, due to fast proton shift within the original electron transfer product protonated semi-methyleneblue MBH*+ and the deprotonated donor radical (N-methyl-9-phenylacridanyl radical AC*) are formed with a rate constant of 2*108 M-1s-1.In this radical pair a second electron is transferred very fast from AC* to MBH*+ with a rate constant ke2 ca. 1010s-1 to form leuco-methyleneblue and N-methyl-9-phenyl-acridinium salt (AC+).About 80percent of the two-equivalent reduction product, leuco-methyleneblue, are formed within the first solvent cage during the flash.The maximum quantum yields of photoreduction approach φisc of MB+ as expected for a two-equivalent reduction reaction.The out-of-cage reaction consists of the known disproportionation of the protonated semi-methyleneblue MBH*+ and its reduction by the N-methyl-9-phenylacridanyl radical AC*.From the decay kinetics kred = 3*109 M-1s-1 and kdis=8*108M-1s-1 is derived.The system sensitizers the dediazoniation of p-N,N-dimethylamino benzenediazonium tetrafluoroborate efficiently even at very low diazonium salt concentrations (Φ = 0.6).

Electrochemistry of the 9-phenyl-10-methyl-acridan/acridinium redox system; a high-potential NADH/NAD+ analogue

Cyclic voltammetry and preparative controlled potential electrolysis show that the 9-phenyl-10-methyl-acridinium/acridan (AcPh+/AcPhH) redox couple can be cycled electrochemically between the oxidized (AcPh+) and reduced states (AcPhH) without any apparent side-reaction.The 9-phenyl-10-methyl-acridanyl radical (AcPh*) was identified as a first intermediate in the electrochemical reduction of AcPh+ by cyclic voltammetry as well as by electronic absorption and ESR spectroscopy.In contrast to other acridanyl and related dihydropyridyl radicals, AcPh* shows no tendency to undergo dimerization.In aprotic media, AcPh. is shown to undergo a second reversible one-electron reduction to yield AcPh-, which is, even in these media readily protonated to give AcPhH.The stability of these intermediates seems to be the major factor responsible for the clean electrochemical interconversion of the AcPh+/AcPhH redox couple.The implementation of this redox couple as part of photo-electrochemical energy conversion systems is discussed.