Journal of Organic Chemistry p. 607 - 612 (1991)
Update date:2022-08-04
Topics:
Ingemann, Steen
Fokkens, Roel H.
Nibbering, Nico M. M.
The proton affinities of the azobenzene radical anion and the conjugate base of hydrazobenzene have been determined to be 1465 kJ mol-1 and 1514 kJ mol-1, respectively, with the use of a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer equipped with an external ion source.The proton affinities lead in combination with a measured electron affinity of azobenzene (55 kJ mol-1) to a N-H bond dissociation energy (BDE) of 306 kJ mol-1 for hydrazobenzene while the N-H BDE of the PhNHN.Ph radical is estimated to be 208 kJ mol-1.The difference between the N-H BDE values of 98 kJ mol-1 approximates the ?-bond energy of the nitrogen-nitrogen bond in azobenzene.The reaction of the PhN.N-Ph and PhNHN-Ph ions with derivatives of trifluoroacetic acid are characterized.The occurrence of dissociative electron transfer instead of SN2 substitution in reactions of the azobenzene radical anion with halogen-substituted methanes is discussed.
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