Dissociation energies of N-H bonds in aromatic amines (review)

Abstract

The review discusses compiled data on the N-H bond dissociation energies of 108 aromatic amines of various structures. A brief description of experimental methods for their determination has been given, and the results obtained by different methods have been compared. Stabilization energies of structur ally different aminyl radicals (ΔE RS ) have been calculated, and this structural energy has been compared with ΔE RS of phenylaminyl and phenoxyl radicals. Values of D N-H , D O-H , and D S-H for a series of hybrid antiox idants (19 compounds) are reported. Bibliography: 42 references.

Rotational Barrier and Bond Dissociation Energy and Enthalpy: Computational Study of the Substituent Effects in <i>Para</i>-Substituted Anilines and Phenols

“…BDEs and BDEts have been calculated experimentally and theoretically for para-substituted anilines and phenols with a very close agreement between the two approaches [2,[24][25][26][27][28][29][30][31]. In almost all theoretical studies, the DFT functional has successfully reproduced the experimental BDEs [24][25]28,30].…”

“…BDEs and BDEts have been calculated experimentally and theoretically for para-substituted anilines and phenols with a very close agreement between the two approaches [2,[24][25][26][27][28][29][30][31]. In almost all theoretical studies, the DFT functional has successfully reproduced the experimental BDEs [24][25]28,30]. It was concluded from the experimental and theoretical studies that EW groups in para position to phenols and anilines increase the N-H and O-H BDE/BDEt, while the opposite is true for ED groups [2,[27][28][29]31].…”

Electronic Database on Experimental Bond Dissociation Energies of Organic Compounds

“…Экспериментальные значения энергий диссоциации связей органических соединений отбирались по следующим методам их определения [18].…”

Substituent effects on the antioxidant capacity of monosubstituted diphenylamines: a DFT study

“…[22] Later on, Poliak et al extensively studied the effects of substituent and substituted position on the N-H BDE values in diphenylamine derivatives using (U)B3LYP/6-311++G(d,p) approach. [23] Presently, several experimental methods [16,[24][25][26][27] and high level computational chemistry approaches [23,[28][29][30][31][32][33][34][35] have been used to determine the BDE(N-H). However, there remains a disadvantage because the computations for molecules with over eight heavy atoms spends a lot of time and requires ultrafast processing speed of computer.…”