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Naphthalene

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Gas phase ion energetics data

Go To: Top, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C10H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.144 ± 0.001eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)802.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity779.4kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
-0.2LPESLyapustina, Xu, et al., 2000Extrapolated from EAs of solvation series naphthalene-...(H2O)n; B
-0.18N/ASong, Han, et al., 2002Extrapolated from LPES EAs of (naphthalene)n; B
-0.200 ± 0.050LPESSchiedt, Knott, et al., 2000Extrapolated from EAs of (H2O)n..naphthalene-. series; B
-0.1908ETSBurrow, Michejda, et al., 1987The question of whether the naphthalene radical anion is bound or not has not been settled; B
0.140 ± 0.050ECDZlatkis, Lee, et al., 1983However, see Heinis, Chowdhury, et al., 1993 for a discussion; it may not be bound.; B
<0.134 ± 0.043ECDWojnarovits and Foldiak, 1981EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.3 eV, anion unbound.; B
0.1480 ± 0.0060ECDBecker and Chen, 1966B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
800.0Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
774.5Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.12 ± 0.02TRPIGotkis, Oleinikova, et al., 1993LL
8.1442 ± 0.0009TECockett, Ozeki, et al., 1993LL
8.12 ± 0.01PIJochims, Rasekh, et al., 1992LL
8.14EIStahl and Maquin, 1984LBLHLM
8.141 ± 0.001LSDuncan, Dietz, et al., 1981LLK
8.08 ± 0.05EQMautner(Meot-Ner), 1980LLK
8.15PESchafer, Schweig, et al., 1975LLK
8.15PESchafer, Schweig, et al., 1973LLK
8.12CTSPitt, 1973LLK
8.15PEClark, Brogli, et al., 1972LLK
8.13PEBrundle, Robin, et al., 1972LLK
8.15PEBrogli, Heilbronner, et al., 1972LLK
8.16 ± 0.03EIJohnstone, Mellon, et al., 1970RDSH
8.11 ± 0.01PEDewar and Worley, 1969RDSH
8.15 ± 0.01PIYencha and El-Sayed, 1968RDSH
8.133SKitagawa, 1968RDSH
8.14PIKitagawa, 1968RDSH
8.12 ± 0.05PEEland and Danby, 1968RDSH
8.136 ± 0.005SAngus, Christ, et al., 1968RDSH
8.25 ± 0.01EIBonnier, Gelus, et al., 1965RDSH
8.15CTSKuroda, 1964RDSH
8.16CTSBriegleb, 1964RDSH
8.08CTSKinoshita, 1962RDSH
8.1PITerenin, 1961RDSH
8.10CTSBirks and Stifkin, 1961RDSH
8.12 ± 0.01PIWatanabe, 1957RDSH
8.14 ± 0.02PIVilesov and Terenin, 1957RDSH
8.09PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
8.15PEKaim, Tesmann, et al., 1980Vertical value; LLK
8.15 ± 0.02PESchmidt, 1977Vertical value; LLK
8.18 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK
8.15PEClar and Schmidt, 1976Vertical value; LLK
8.31 ± 0.03PEMarschner and Goetz, 1974Vertical value; LLK
8.15PEBock, Wagner, et al., 1972Vertical value; LLK
8.15PEBock and Wagner, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+19.35?PIJochims, Rasekh, et al., 1993LL
C3H3+19.2 ± 0.1C3H3+C4H2PIJochims, Rasekh, et al., 1992LL
C4H2+20.7 ± 0.13C2H2PIJochims, Rasekh, et al., 1992LL
C4H3+22.3 ± 0.12C2H2+C2HPIJochims, Rasekh, et al., 1992LL
C4H4+19.4 ± 0.1C4H2+C2H2PIJochims, Rasekh, et al., 1992LL
C4H4+19.6 ± 0.20?EIVanBrunt and Wacks, 1964RDSH
C5H3+19.74?PIJochims, Rasekh, et al., 1993LL
C5H3+19.7 ± 0.1C2H2+C3H3PIJochims, Rasekh, et al., 1992LL
C6H3+20.77 ± 0.01?EIVanBrunt and Wacks, 1964RDSH
C6H4+18.7 ± 0.12C2H2PIJochims, Rasekh, et al., 1992LL
C6H4+18.2 ± 0.15?EIVanBrunt and Wacks, 1964RDSH
C6H5+18.72?PIJochims, Rasekh, et al., 1993LL
C6H5+18.6 ± 0.1C2H2+C2HPIJochims, Rasekh, et al., 1992LL
C6H5+18.45 ± 0.05?EIVanBrunt and Wacks, 1964RDSH
C6H6+15.64C4H2PIJochims, Rasekh, et al., 1993LL
C6H6+15.7 ± 0.1C4H2PIJochims, Rasekh, et al., 1992LL
C6H6+15.20 ± 0.05?EIVanBrunt and Wacks, 1964RDSH
C7H3+20.66 ± 0.15C3H3+H2PIJochims, Rasekh, et al., 1992LL
C7H5+15.90C3H3PIJochims, Rasekh, et al., 1993LL
C7H5+16.1 ± 0.1C3H3PIJochims, Rasekh, et al., 1992LL
C8H5+19.00 ± 0.05C2H2+HPIJochims, Rasekh, et al., 1992LL
C8H5+18.07 ± 0.05?EIVanBrunt and Wacks, 1964RDSH
C8H6+15.50C2H2PIJochims, Rasekh, et al., 1993LL
C8H6+12.74C2H2EVALGotkis, Oleinikova, et al., 1993T = 0K; LL
C8H6+14.43C2H2TRPIGotkis, Oleinikova, et al., 1993LL
C8H6+15.4 ± 0.1C2H2PIJochims, Rasekh, et al., 1992LL
C8H6+15.4 ± 0.10C2H2EIVanBrunt and Wacks, 1964RDSH
C10H6+15.60 ± 0.05H2PIJochims, Rasekh, et al., 1992LL
C10H6+16.2 ± 0.15H2EIVanBrunt and Wacks, 1964RDSH
C10H7+15.41HPIJochims, Rasekh, et al., 1993LL
C10H7+12.37HEVALGotkis, Oleinikova, et al., 1993T = 0K; LL
C10H7+14.24HTRPIGotkis, Oleinikova, et al., 1993LL
C10H7+15.4 ± 0.1HPIJochims, Rasekh, et al., 1992LL
C10H7+15.4 ± 0.10HEIVanBrunt and Wacks, 1964RDSH

De-protonation reactions

C10H7- + Hydrogen cation = Naphthalene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Deltar1649. ± 5.0kJ/molBranReed and Kass, 2000gas phase; B
Deltar1649. ± 5.0kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar1648. ± 21.kJ/molCIDCLardin, Squires, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Deltar1613. ± 5.4kJ/molH-TSReed and Kass, 2000gas phase; B
Deltar1606. ± 5.0kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar1613. ± 21.kJ/molH-TSLardin, Squires, et al., 2001gas phase; B

C10H7- + Hydrogen cation = Naphthalene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Deltar1655. ± 5.4kJ/molBranReed and Kass, 2000gas phase; B
Quantity Value Units Method Reference Comment
Deltar1619. ± 5.9kJ/molH-TSReed and Kass, 2000gas phase; B

References

Go To: Top, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Lyapustina, Xu, et al., 2000
Lyapustina, S.A.; Xu, S.K.; Nilles, J.M.; Bowen, K.H., Solvent-induced stabilization of the naphthalene anion by water molecules: A negative cluster ion photoelectron spectroscopic study, J. Chem. Phys., 2000, 112, 15, 6643-6648, https://doi.org/10.1063/1.481237 . [all data]

Song, Han, et al., 2002
Song, J.K.; Han, S.Y.; Chu, I.H.; Kim, J.H.; Kim, S.K.; Lyapustina, S.A.; Xu, S.J.; Nilles, J.M.; Bowen, K.H., Photoelectron spectroscopy of naphthalene cluster anions, J. Chem. Phys., 2002, 116, 11, 4477-4481, https://doi.org/10.1063/1.1449869 . [all data]

Schiedt, Knott, et al., 2000
Schiedt, J.; Knott, W.J.; Le Barbu, K.; Schlag, E.W.; Weinkauf, R., Microsolvation of similar-sized aromatic molecules: Photoelectron spectroscopy of bithiophene-, azulene-, and naphthalene-water anion clusters, J. Chem. Phys., 2000, 113, 21, 9470-9478, https://doi.org/10.1063/1.1319874 . [all data]

Burrow, Michejda, et al., 1987
Burrow, P.D.; Michejda, J.A.; Jordan, K.D., Electron Transmission Study of the Temporary Negative Ion States of Selected Benzenoid and Conjugated Aromatic Hydrocarbons., J. Chem. Phys., 1987, 86, 1, 9, https://doi.org/10.1063/1.452598 . [all data]

Zlatkis, Lee, et al., 1983
Zlatkis, A.; Lee, C.K.; Wentworth, W.E.; Chen, E.C.M., Constant current linearization for determination of electron capture mechanisms, Anal. Chem., 1983, 55, 1596. [all data]

Heinis, Chowdhury, et al., 1993
Heinis, T.; Chowdhury, S.; Kebarle, P., Electron Affinities of Naphthalene, Anthracene and Substituted Naphthalenes and Anthracenes, Org. Mass Spectrom., 1993, 28, 4, 358, https://doi.org/10.1002/oms.1210280416 . [all data]

Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G., Electron capture detection of aromatic hydrocarbons, J. Chromatogr. Sci., 1981, 206, 511. [all data]

Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E., Experimental Determination of Electron Affinities of Organic Molecules, Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]

Becker and Chen, 1966
Becker, R.S.; Chen, E., Extension of Electron Affinities and Ionization Potentials of Aromatic Hydrocarbons, J. Chem. Phys., 1966, 45, 7, 2403, https://doi.org/10.1063/1.1727954 . [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Gotkis, Oleinikova, et al., 1993
Gotkis, Y.; Oleinikova, M.; Naor, M.; Lifshitz, C., Time-independent mass spectra and breakdown graphs. 17. Naphthalene and phenanthrene, J. Phys. Chem., 1993, 97, 12282. [all data]

Cockett, Ozeki, et al., 1993
Cockett, M.C.R.; Ozeki, H.; Okuyama, K.; Kimura, K., Vibronic coupling in the ground cationic state of naphthalene: A laser threshold photoelectron [zero kinetic energy (ZEKE)-photoelectron] spectroscopic study, J. Chem. Phys., 1993, 98, 7763. [all data]

Jochims, Rasekh, et al., 1992
Jochims, H.-W.; Rasekh, H.; Ruhl, E.; Baumgartel, H.; Leach, S., The photofragmentation of naphthalene and azulene monocations in the energy range 7-22 eV, Chem. Phys., 1992, 168, 159. [all data]

Stahl and Maquin, 1984
Stahl, D.; Maquin, F., Charge-stripping mass spectrometry of molecular ions from polyacenes and molecular orbital theory, Chem. Phys. Lett., 1984, 108, 613. [all data]

Duncan, Dietz, et al., 1981
Duncan, M.A.; Dietz, T.G.; Smalley, R.E., Two-color photoionization of naphthalene and benzene at threshold, J. Chem. Phys., 1981, 75, 2118. [all data]

Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M., Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite, J. Phys. Chem., 1980, 84, 2716. [all data]

Schafer, Schweig, et al., 1975
Schafer, W.; Schweig, A.; Vermeer, H.; Bickel-haupt, F.; De Graaf, H., On the nature of the "free electron pair" on phosphorus in aromatic phosphorus compounds: the photoelectron spectrum of 2-phosphanaphthalene, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 91. [all data]

Schafer, Schweig, et al., 1973
Schafer, W.; Schweig, A.; Markl, G.; Heier, K.-H., Zur elektronenstruktur der lambda3- und lambda5-phosphanaphthaline--ungewohnlich grosse MO destabilisierungen, Tetrahedron Lett., 1973, 3743. [all data]

Pitt, 1973
Pitt, C.G., Hyperconjugation and its role in group IV chemistry, J. Organomet. Chem., 1973, 61, 49. [all data]

Clark, Brogli, et al., 1972
Clark, P.A.; Brogli, F.; Heilbronner, E., The «pi»-orbital energies of the acenes, Helv. Chim. Acta, 1972, 55, 1415. [all data]

Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A., Perfluoro effect in photoelectron spectroscopy. II. Aromatic molecules, J. Am. Chem. Soc., 1972, 94, 1466. [all data]

Brogli, Heilbronner, et al., 1972
Brogli, F.; Heilbronner, E.; Kobayashi, T., Photoelectron spectra of azabenzenes and azanaphthalenes: II. A reinvestigation of azanaphthalenes by high-resolution photoelectron spectroscopy, Helv. Chim. Acta, 1972, 55, 274. [all data]

Johnstone, Mellon, et al., 1970
Johnstone, R.A.W.; Mellon, F.A.; Ward, S.D., Online acquisition of ionization efficiency data, Intern. J. Mass Spectrom. Ion Phys., 1970, 5, 241. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Yencha and El-Sayed, 1968
Yencha, A.J.; El-Sayed, M.A., Lowest ionization potentials of some nitrogen heterocyclics, J. Chem. Phys., 1968, 48, 3469. [all data]

Kitagawa, 1968
Kitagawa, T., Absorption spectra and photoionization of polycyclic aromatics in vacuum ultraviolet region, J. Mol. Spectry., 1968, 26, 1. [all data]

Eland and Danby, 1968
Eland, J.H.D.; Danby, C.J., Inner ionization potentials of aromatic compounds, Z. Naturforsch., 1968, 23a, 355. [all data]

Angus, Christ, et al., 1968
Angus, J.G.; Christ, B.J.; Morris, G.C., Absorption spectra in the vacuum ultraviolet and the ionization potentials of naphthalene and naphthalene-d, molecules, Australian J. Chem., 1968, 21, 2153. [all data]

Bonnier, Gelus, et al., 1965
Bonnier, J.-M.; Gelus, M.; Nounou, P., Contribution a l'etude de l'effet inductif et de l'effet d'hyperconjugaison dans quelques methylaromatiques, J. Chim. Phys., 1965, 10, 1191. [all data]

Kuroda, 1964
Kuroda, H., Ionization potentials of polycyclic aromatic hydrocarbons, Nature, 1964, 201, 1214. [all data]

Briegleb, 1964
Briegleb, G., Electron affinity of organic molecules, Angew. Chem. Intern. Ed., 1964, 3, 617. [all data]

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]

Terenin, 1961
Terenin, A., Charge transfer in organic solids, induced by light, Proc. Chem. Soc., London, 1961, 321. [all data]

Birks and Stifkin, 1961
Birks, J.B.; Stifkin, M.A., «pi»-Electronic excitation and ionization energies of condensed ring aromatic hydrocarbons, Nature, 1961, 191, 761. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H., Photoelectron spectra of acenes. Electronic structure and substituent effects, Pure Appl. Chem., 1983, 55, 289. [all data]

Kaim, Tesmann, et al., 1980
Kaim, W.; Tesmann, H.; Bock, H., Me3C-, Me3Si-, Me3Ge-, Me3Sn- und Me3Pb-substituierte benzol- und naphthalin-derivate und ihre radikalanionen, Chem. Ber., 1980, 113, 3221. [all data]

Schmidt, 1977
Schmidt, W., Photoelectron spectra of polynuclear aromatics. V. Correlations with ultraviolet absorption spectra in the catacondensed series, J. Chem. Phys., 1977, 66, 828. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the 2A<--2X and 2B<--2X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Clar and Schmidt, 1976
Clar, E.; Schmidt, W., Correlations between photoelectron and phosphorescence spectra of polycyclic hydrocarbons, Tetrahedron, 1976, 32, 2563. [all data]

Marschner and Goetz, 1974
Marschner, F.; Goetz, H., Korrelation zwischen photoelektronen- und elektronen-spektren. II. Untersuchung aromatischer «pi»-systeme mit modifizierten PPP-SCF-CI-parametern, Tetrahedron, 1974, 30, 3159. [all data]

Bock, Wagner, et al., 1972
Bock, H.; Wagner, G.; Kroner, J., Photoelektronenspektren und molekuleigenschaften, XIV. Die delokalisation des schwefel-elektronenpaar in CH3S-substituierten aromaten, Chem. Ber., 1972, 105, 3850. [all data]

Bock and Wagner, 1972
Bock, H.; Wagner, G., Electron lone pairs in organic sulfides and disulfides, Angew. Chem. Int. Ed. Engl., 1972, 11, 119. [all data]

Jochims, Rasekh, et al., 1993
Jochims, H.-W.; Rasekh, H.; Ruhl, E.; Baumgartel, H.; Leach, S., Deuterium isotope effects in the photofragmentation of naphthalene monocations, J. Phys. Chem., 1993, 97, 1312. [all data]

VanBrunt and Wacks, 1964
VanBrunt, R.J.; Wacks, M.E., Electron-impact studies of aromatic hydrocarbons. III. Azulene and naphthalene, J. Chem. Phys., 1964, 41, 3195. [all data]

Reed and Kass, 2000
Reed, D.R.; Kass, S.R., Experimental determination of the alpha and beta C-H bond dissociation energies in naphthalene, J. Mass Spectrom., 2000, 35, 4, 534-539, https://doi.org/10.1002/(SICI)1096-9888(200004)35:4<534::AID-JMS964>3.0.CO;2-T . [all data]

Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A., Ionic Probes of Aromaticity in Annelated Rings, J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

Lardin, Squires, et al., 2001
Lardin, H.A.; Squires, R.R.; Wenthold, P.G., Determination of the electron affinities of alpha- and beta- naphthyl radicals using the kinetic method with full entropy analysis. The C-H bond dissociation energies of naphthalene, J. Mass Spectrom., 2001, 36, 6, 607-615, https://doi.org/10.1002/jms.159 . [all data]


Notes

Go To: Top, Gas phase ion energetics data, References