Abstract
The N—H bond dissociation energy (D NH) in the 4-anilinodiphenylaminyl radical formed from N,N′-diphenyl-1,4-phenylenediamine was experimentally determined and calculated by the quantum-chemical method. The experimental D NH value was found from the enthalpy of the reaction of N,N′-diphenyl-1,4-benzoquinonediimine with 4-hydroxydiphenylamine taking into account the bond dissociation energies in 4-hydroxydiphenylamine and its aminyl and phenoxyl radicals, which were determined by the intersecting parabolas method from the kinetic data. The quantum-chemical calculations of D NH used several semiempirical methods by the MOPAC program and the ab initio and DFT methods by the GAUSSIAN 94/98 program. The D NH values, which were closest to the experimental values, were obtained by the B3LYP/6-31+G* method. The results of quantum-chemical calculations of the N—H and O—H bond dissociation energies in 4-hydroxydiphenylamine and its radicals are presented.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1549–1554, August, 2004.
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Varlamov, V.T., Krisyuk, B.E. N—H bond dissociation energies in N,N′-diphenyl-1,4-phenylenediamine and its aminyl radical. Russ Chem Bull 53, 1609–1614 (2004). https://doi.org/10.1007/s11172-005-0004-2
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DOI: https://doi.org/10.1007/s11172-005-0004-2