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Experimental determination of the α and β C—H bond dissociation energies in naphthalene
Author(s) -
Reed Dana R.,
Kass Steven R.
Publication year - 2000
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(200004)35:4<534::aid-jms964>3.0.co;2-t
Subject(s) - chemistry , naphthalene , bond dissociation energy , radical , benzene , dissociation (chemistry) , ab initio , mass spectrometry , density functional theory , hydrogen bond , bond energy , computational chemistry , medicinal chemistry , molecule , organic chemistry , chromatography
The acidities of the two different sites in naphthalene (1 α and 1 β ) 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 $\Delta {\it H}^{\circ}_{\rm acid}({\bf 1}\alpha) = 394.2 \pm 1.2 \hbox{ kcal mol}^{-1}$ , $\Delta {\it H}^{\circ}_{\rm acid}({\bf 1}\beta) = 395.5 \pm 1.3 \hbox{ kcal mol}^{-1}$ , EA( α ) = 31.6 ± 0.5kcal mol −1 , EA( β ) = 31.6 ± 0.5kcal mol −1 , BDE( 1 α ) = 112.2 ± 1.3kcal mol −1 and BDE( 1 α ) = 111.9 ± 1.4kcal mol −1 , and they are compared to benzene and phenyl radical as well as ab initio and density functional theory (B3LYP) calculations. Copyright © 2000 John Wiley & Sons, Ltd.