Electron spin resonance study of hindered internal rotation in the 3,5-dinitrobenzamide radical anion and related compounds

Barzaghi, Mario; Oliva, Cesare; Simonetta, M.

doi:10.1021/j100452a019

Cited by 13 publications

References 19 publications

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Substituent effects on the intramolecular electron exchange reaction in 5‐substituted 1,3‐dinitrobenzene radical anions

Telo¹,

Shohoji²

1994

Ber Bunsenges Phys Chem

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Nine new radical anions of 1,3-dinitrobenzenes with various substituents on position 5 (2, 3, 5-7, 9-11 and 13) were prepared by electrochemical reduction in acetonitrile and studied by EPR at temperatures between 240 K and 320 K. Another eight known radicals of the same type were reexamined in the same conditions in order to complete the set of data. Their EPR spectra showed alternating linebroadening effects due to intramolecular electron exchange induced by asymmetric solvation of the two nitro groups. Rate constants at 293 K range from 1 . 4~ lo9 s-' (3,5-dinitrophenolate) to 1 . 2~ 10" s-' (3,5-dinitrobenzonitrile). Good Hammett correlations between the rate constants of intramolecular electron exchange and the parameter u, of the substituent on position 5 were obtained. The reaction is accelerated by electron withdrawing groups. p values range from 0.95 at 240 K to 0.74 at 320 K. Activation parameters were estimated by using the Rips and Jortner equation for the rate constant of a uniform adiabatic reaction. AG* was found to increase with the electron donating ability of the substituent, mainly due to an increase of the interaction between the reactants and the solvent. The pre-exponential factor A is constant within the experimental error, as predicted by theory.

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Substituent effects on the intramolecular electron exchange reaction in 5‐substituted 1,3‐dinitrobenzene radical anions

Telo¹,

Shohoji²

1994

Ber Bunsenges Phys Chem

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ChemInform Abstract: ELECTRON SPIN RESONANCE STUDY OF HINDERED INTERNAL ROTATION IN THE 3,5‐DINITROBENZAMIDE RADICAL ANION AND RELATED COMPOUNDS

Barzaghi¹,

Oliva²,

Simonetta³

1980

Chemischer Informationsdienst

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Electron spin resonance studies of several anion radicals of nitro‐substituted thioacylpiperidines and morpholines

Cercasov¹,

Cornea²,

Ciureanu³

et al. 1982

Org. Magn. Reson.

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The radical anions of rn-and p nitro-substituted derivatives of several classes of N-(thioacy1)-piperidnes and morpholines have been studied by ESR spectroscopy. The anion radicals were found to be centred on the nitro group, and the distribution of the unpaired electron was found to be dependent on the extent of conjugation between the thiocarbonyl group and the aromatic moiety of the molecule. The hfs constants were discussed in terms of the spin densities calculated by the McLachlan procedure.

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Electron spin resonance study of hindered internal rotation in the 3,5-dinitrobenzamide radical anion and related compounds

Cited by 13 publications

References 19 publications

Substituent effects on the intramolecular electron exchange reaction in 5‐substituted 1,3‐dinitrobenzene radical anions

Substituent effects on the intramolecular electron exchange reaction in 5‐substituted 1,3‐dinitrobenzene radical anions

ChemInform Abstract: ELECTRON SPIN RESONANCE STUDY OF HINDERED INTERNAL ROTATION IN THE 3,5‐DINITROBENZAMIDE RADICAL ANION AND RELATED COMPOUNDS

Electron spin resonance studies of several anion radicals of nitro‐substituted thioacylpiperidines and morpholines

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