Tertiary aminomethylphenols and methylene bisphenols with isobornyl substituents in the reaction with diphenylpicrylhydrazyl and peroxy radicals in ethylbenzene
Abstract
The effect of the structure of aminomethylphenols and methylene bisphenols with isobornyl substituents on their reactivity in interactions with peroxy radicals in ethylbenzene and with 1,1-diphenyl-2-picrylhydrazyl (DPPH) is studied. Isobornylphenols with o-aminomethyl substituents, as opposed to p-aminomethyl derivatives, were found to possess rather low activity in the initiated oxidation of ethylbenzene, due to the formation of intramolecular hydrogen bonds between the hydrogen atom of the OH group and the nitrogen atom of the aminomethyl substituent. An increase in activity of o-aminomethyl-substituted phenols with increasing polarity of the medium is observed in the reaction with DPPH. The reaction rate constants for the interaction between two isomeric 2,2'- and 4,4'-methylene-bisphenols having isobornyl moieties and ethylbenzene peroxy radicals are measured. The ratio between activities of the first and second OH groups in 2,2-methylene-bisphenol is shown to be close to 50.
- Publication:
-
Russian Journal of Physical Chemistry A
- Pub Date:
- April 2013
- DOI:
- 10.1134/S0036024413040171
- Bibcode:
- 2013RJPCA..87..565M
- Keywords:
-
- tertiary aminomethylphenols;
- methylene bisphenols;
- peroxy radicals;
- 1;
- 1-diphenyl-2-picrylhydrazyl;
- antiradical activity;
- medium polarity;
- hydrogen bonds