Naphthalene

• Formula: C₁₀H₈
• Molecular weight: 128.1705
• IUPAC Standard InChI: InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H Copy

  
• IUPAC Standard InChIKey: UFWIBTONFRDIAS-UHFFFAOYSA-N Copy
• CAS Registry Number: 91-20-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Isotopologues:
  • Naphthalene-D8
• Other names: Albocarbon; Dezodorator; Moth flakes; Naphthalin; Naphthaline; Naphthene; Tar camphor; White tar; Camphor tar; Moth balls; Naftalen; NCI-C52904; Mighty 150; Mighty RD1; Rcra waste number U165; UN 1334; UN 2304; NSC 37565
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Reaction thermochemistry 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 compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₁₀H₇^- +  =

By formula: C₁₀H₇^- + H⁺ = C₁₀H₈

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₁₀H₈ = (C₆H₇N⁺ • C₁₀H₈)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₁₂H₈⁺ +  = (C₁₂H₈⁺ • )

By formula: C₁₂H₈⁺ + C₁₀H₈ = (C₁₂H₈⁺ • C₁₀H₈)

Bond type: Charge transfer bond (positive ion)

C₁₂H₉⁺ +  = (C₁₂H₉⁺ • )

By formula: C₁₂H₉⁺ + C₁₀H₈ = (C₁₂H₉⁺ • C₁₀H₈)

Bond type: Charge transfer bond (positive ion)

2 +  =

By formula: 2H₂ + C₁₀H₈ = C₁₀H₁₂

=

By formula: C₁₀H₈ = C₁₀H₈

C₁₀H₈⁺ +  = (C₁₀H₈⁺ • )

By formula: C₁₀H₈⁺ + C₁₀H₈ = (C₁₀H₈⁺ • C₁₀H₈)

Bond type: Charge transfer bond (positive ion)

C₁₀H₇^- +  =

By formula: C₁₀H₇^- + H⁺ = C₁₀H₈

H₄O₄^- +  + 2 = C₁₀H₁₂O₄^-

By formula: H₄O₄^- + C₁₀H₈ + 2H₂O = C₁₀H₁₂O₄^-

H₂O₃^- +  +  = C₁₀H₁₀O₃^-

By formula: H₂O₃^- + C₁₀H₈ + H₂O = C₁₀H₁₀O₃^-

C₁₀H₉⁺ +  = (C₁₀H₉⁺ • )

By formula: C₁₀H₉⁺ + C₁₀H₈ = (C₁₀H₉⁺ • C₁₀H₈)

 +  = C₁₀H₈O₂^-

By formula: O₂^- + C₁₀H₈ = C₁₀H₈O₂^-

 +  = C₁₀H₈NO^-

By formula: NO^- + C₁₀H₈ = C₁₀H₈NO^-

C₁₀H₈NO^- + 2 = C₂₀H₁₆NO^-

By formula: C₁₀H₈NO^- + 2C₁₀H₈ = C₂₀H₁₆NO^-

5 +  =

By formula: 5H₂ + C₁₀H₈ = C₁₀H₁₈

References

Go To: Top, Reaction thermochemistry data, Notes

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

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]

El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M., Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors, J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017 . [all data]

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [all data]

Frye and Weitkamp, 1969
Frye, C.G.; Weitkamp, A.W., Equilibrium hydrogenations of multi-ring aromatics, J. Chem. Eng. Data, 1969, 14, 372-376. [all data]

Wilson, Caflisch, et al., 1958
Wilson, T.P.; Caflisch, E.G.; Hurley, G.F., The naphthalene-tetralin-hydrogen equilibrium at elevated temperature and pressure, J. Phys. Chem., 1958, 62, 1059. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Dreeskamp, Kapahnke, et al., 1988
Dreeskamp, H.; Kapahnke, P.; Tochtermann, W., Photo valence isomerization of sterically strained aromatic hydrocarbons: 8,9-dicarbethoxy[6]paracyclophane, Radiat. Phys. Chem., 1988, 32, 537-539. [all data]

Grimme and Heinze, 1978
Grimme, W.; Heinze, U., Kinetics and enthalpy of isomerization of benzobicyclo[2.2.0]hexa-2,5-diene, Chem. Ber., 1978, 111, 2563-2570. [all data]

Le Barbu, Schiedt, et al., 2002
Le Barbu, K.; Schiedt, J.; Weinkauf, R.; Schlag, E.W.; Nilles, J.M.; Xu, S.J.; Thomas, O.C.; Bowen, K.H., Microsolvation of small anions by aromatic molecules: An exploratory study, J. Chem. Phys., 2002, 116, 22, 9663-9671, https://doi.org/10.1063/1.1475750 . [all data]

Notes

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:
  

  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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