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Reaction sites of N,N′-substituted p-phenylenediamine antioxidants

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Abstract

The geometries of N,N′-diphenylbenzene-1,4-diamine (DPPD), N-phenyl-N′-(1-phenylethyl)benzene-1,4-diamine (SPPD), N-(4-methylpentan-2-yl)-N′-phenylbenzene-1,4-diamine (6PPD), N-propan-2-yl-N′-phenylbenzene-1,4-diamine (IPPD), N-(2-methoxybenzyl)-N′-phenylbenzene-1,4-diamine (MBPPD), and N-phenyl-N′-(2-phenylpropan-2-yl)benzene-1,4-diamine (CPPD) as well as of their dehydrogenation products were optimized by the semiempirical AM1 method. The results support the idea of stable NB=CX structures formation during the consecutive dehydrogenation of SPPD, 6PPD, IPPD, and MBPPD antioxidants. The biradicals formed during the second step of dehydrogenation of substituted phenylenediamines might be important for their antioxidant effectiveness.

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Authors and Affiliations

  1. Department of Physical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, SK-812 37, Bratislava, Slovakia

    I. Kortišová, M. Breza & Z. Cibulková

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  1. I. Kortišová
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  2. M. Breza
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  3. Z. Cibulková
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Dedicated to Professor Vladimír Kvasnička, DrSc., in honour of his 65th birthday

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Kortišová, I., Breza, M. & Cibulková, Z. Reaction sites of N,N′-substituted p-phenylenediamine antioxidants. Chem. Pap. 61, 61–65 (2007). https://doi.org/10.2478/s11696-006-0097-6

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  • DOI: https://doi.org/10.2478/s11696-006-0097-6

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