220 MHz nuclear magnetic resonance analysis and selective deuteriodeprotonation of benzo[a]pyrene and 6-methylbenzo[a]pyrene

Ercole Cavalieri, M. Calvin

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18 Citations (Scopus)

Abstract

An analysis of the 220 MHz magnetic resonance spectra of the carcinogenic benzo[a]pyrene (1) and 6-methylbenzo[a]pyrene (2) is presented. A study of proton exchange in sulphuric [2H2]acid is used to determine the specific positions of electrophilic substitution. Electrophilic attack on compound (1) takes place predominantly at the 6-position, and then at the 1- and 3-positions, whereas in compound (2) the most active positions are C-1, C-3, and C-5, with C-5 the least active of the three.

Original languageEnglish (US)
Pages (from-to)1253-1256
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
StatePublished - Dec 1 1972

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Benzo(a)pyrene
Magnetic resonance
Protons
Substitution reactions
Nuclear magnetic resonance
Acids
6-methylbenzo(a)pyrene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "220 MHz nuclear magnetic resonance analysis and selective deuteriodeprotonation of benzo[a]pyrene and 6-methylbenzo[a]pyrene",
abstract = "An analysis of the 220 MHz magnetic resonance spectra of the carcinogenic benzo[a]pyrene (1) and 6-methylbenzo[a]pyrene (2) is presented. A study of proton exchange in sulphuric [2H2]acid is used to determine the specific positions of electrophilic substitution. Electrophilic attack on compound (1) takes place predominantly at the 6-position, and then at the 1- and 3-positions, whereas in compound (2) the most active positions are C-1, C-3, and C-5, with C-5 the least active of the three.",
author = "Ercole Cavalieri and M. Calvin",
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N2 - An analysis of the 220 MHz magnetic resonance spectra of the carcinogenic benzo[a]pyrene (1) and 6-methylbenzo[a]pyrene (2) is presented. A study of proton exchange in sulphuric [2H2]acid is used to determine the specific positions of electrophilic substitution. Electrophilic attack on compound (1) takes place predominantly at the 6-position, and then at the 1- and 3-positions, whereas in compound (2) the most active positions are C-1, C-3, and C-5, with C-5 the least active of the three.

AB - An analysis of the 220 MHz magnetic resonance spectra of the carcinogenic benzo[a]pyrene (1) and 6-methylbenzo[a]pyrene (2) is presented. A study of proton exchange in sulphuric [2H2]acid is used to determine the specific positions of electrophilic substitution. Electrophilic attack on compound (1) takes place predominantly at the 6-position, and then at the 1- and 3-positions, whereas in compound (2) the most active positions are C-1, C-3, and C-5, with C-5 the least active of the three.

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