Reaction of Methylbenzanthracenes and Pyridine by One-Electron Oxidation. A Model for Metabolic Activation and Binding of Carcinogenic Aromatic Hydrocarbons

Ercole Cavalieri, Robert Roth

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39 Citations (Scopus)

Abstract

A simple procedure for generation and trapping of polycyclic aromatic hydrocarbon radical cations in homogeneous solutions of pyridine and iodine is described. Radical cations of benz[a]anthracene and its alkyl derivatives are trapped by nucleophilic attack of pyridine on the aromatic nucleus in the order C-7 > C-12 > C-5. When positions 7 or 7 and 12 are blocked by a methyl group, pyridine substitution on the alkyl group competes with ring substitution. Mechanisms for the two types of substitution are proposed and trapping specificity is discussed in terms of charge density and steric factors in the radical ions.

Original languageEnglish (US)
Pages (from-to)2679-2684
Number of pages6
JournalJournal of Organic Chemistry
Volume41
Issue number16
DOIs
StatePublished - Aug 1 1976

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Aromatic Hydrocarbons
Substitution reactions
Chemical activation
Oxidation
Cations
Electrons
Polycyclic Aromatic Hydrocarbons
Charge density
Iodine
Ions
Derivatives
pyridine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "A simple procedure for generation and trapping of polycyclic aromatic hydrocarbon radical cations in homogeneous solutions of pyridine and iodine is described. Radical cations of benz[a]anthracene and its alkyl derivatives are trapped by nucleophilic attack of pyridine on the aromatic nucleus in the order C-7 > C-12 > C-5. When positions 7 or 7 and 12 are blocked by a methyl group, pyridine substitution on the alkyl group competes with ring substitution. Mechanisms for the two types of substitution are proposed and trapping specificity is discussed in terms of charge density and steric factors in the radical ions.",
author = "Ercole Cavalieri and Robert Roth",
year = "1976",
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language = "English (US)",
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pages = "2679--2684",
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T1 - Reaction of Methylbenzanthracenes and Pyridine by One-Electron Oxidation. A Model for Metabolic Activation and Binding of Carcinogenic Aromatic Hydrocarbons

AU - Cavalieri, Ercole

AU - Roth, Robert

PY - 1976/8/1

Y1 - 1976/8/1

N2 - A simple procedure for generation and trapping of polycyclic aromatic hydrocarbon radical cations in homogeneous solutions of pyridine and iodine is described. Radical cations of benz[a]anthracene and its alkyl derivatives are trapped by nucleophilic attack of pyridine on the aromatic nucleus in the order C-7 > C-12 > C-5. When positions 7 or 7 and 12 are blocked by a methyl group, pyridine substitution on the alkyl group competes with ring substitution. Mechanisms for the two types of substitution are proposed and trapping specificity is discussed in terms of charge density and steric factors in the radical ions.

AB - A simple procedure for generation and trapping of polycyclic aromatic hydrocarbon radical cations in homogeneous solutions of pyridine and iodine is described. Radical cations of benz[a]anthracene and its alkyl derivatives are trapped by nucleophilic attack of pyridine on the aromatic nucleus in the order C-7 > C-12 > C-5. When positions 7 or 7 and 12 are blocked by a methyl group, pyridine substitution on the alkyl group competes with ring substitution. Mechanisms for the two types of substitution are proposed and trapping specificity is discussed in terms of charge density and steric factors in the radical ions.

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