Experimental determination of the α and β C-H bond dissociation energies in naphthalene

Dana R. Reed, Steven R. Kass

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52 Scopus citations

Abstract

The acidities of the two different sites in naphthalene (1α and 1β) and the electron affinities of the α- and β-naphthyl radicals were measured using a Fourier transform mass spectrometer. Both carbon-hydrogen bond dissociation energies for naphthalene also were obtained, in this case via the application of a thermodynamic cycle. The final results are ΔH(acid)(o) (1α) = 394.2 ± 1.2 kcal mol-1, ΔH(acid)(o) (1β) = 395.5 ± 1.3 kcal mol-1, EA(α) = 31.6 ± 0.5 kcal mol-1, EA(β) = 31.6 ± 0.5 kcal mol-1, BDE(1α) = 112.2 ± 1.3 kcal mol-1 and BDE(1α) = 111.9 ± 1.4 kcal mol-1, and they are compared to benzene and phenyl radical as well as ab initio and density functional theory (B3LYP) calculations. Copyright (C) 2000 John Wiley and Sons, Ltd.

Original languageEnglish (US)
Pages (from-to)534-539
Number of pages6
JournalJournal of Mass Spectrometry
Volume35
Issue number4
DOIs
StatePublished - 2000

Keywords

  • Bond dissociation energy
  • Electron affinity
  • Fourier transform mass spectrometry
  • Gas-phase acidity
  • Naphthalene

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