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:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.