Naphthalene, 1-methyl-

• Formula: C₁₁H₁₀
• Molecular weight: 142.1971
• IUPAC Standard InChI: InChI=1S/C11H10/c1-9-5-4-7-10-6-2-3-8-11(9)10/h2-8H,1H3 Copy

  
• IUPAC Standard InChIKey: QPUYECUOLPXSFR-UHFFFAOYSA-N Copy
• CAS Registry Number: 90-12-0
• 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.
• Other names: α-Methylnaphthalene; 1-Methylnaphthalene; Methyl-1-naphthalene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law 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
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Condensed phase thermochemistry data

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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Reaction thermochemistry data

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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

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

C₁₁H₉^- +  =

By formula: C₁₁H₉^- + H⁺ = C₁₁H₁₀

C₁₁H₁₀⁺ +  = (C₁₁H₁₀⁺ • )

By formula: C₁₁H₁₀⁺ + C₁₁H₁₀ = (C₁₁H₁₀⁺ • C₁₁H₁₀)

Bond type: Charge transfer bond (positive ion)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₁₁H₁₀ = (C₆H₇N⁺ • C₁₁H₁₀)

Bond type: Charge transfer bond (positive ion)

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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
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 C₁₁H₁₀⁺ (ion structure unspecified)

Electron affinity determinations

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₁₁H₉^- +  =

By formula: C₁₁H₉^- + H⁺ = C₁₁H₁₀

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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.

Speros and Rossini, 1960
Speros, D.M.; Rossini, F.D., Heats of combustion and formation of naphthalene, the two methylnaphthalenes, cis and trans decahydronaphthalene and related compounds, J. Phys. Chem., 1960, 64, 1723-1727. [all data]

Balcan, Arzik, et al., 1996
Balcan, M.; Arzik, S.; Altunata, T., The determination of the heats of combustion and the resonance energies of some substituted naphthalenes, Thermochim. Acta, 1996, 278, 49-56. [all data]

Hipsher and Wise, 1954
Hipsher, H.F.; Wise, P.H., Dicyclic hydrocarbons. VIII. 1-Alkylnaphthalenes and some of their tetrahydro derivatives, J. Am. Chem. Soc., 1954, 76, 1747-1748. [all data]

McCullough, Finke, et al., 1957
McCullough, J.P.; Finke, H.L.; Messerly, J.F.; Kincheloe, T.C.; Waddington, G., The low temperature thermodynamic properties of naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, 1,2,3,4-tetrahydronaphthalene, trans-decahydronaphthalene and cis-decahydronaphthalene, J. Phys. Chem., 1957, 61, 1105-1116. [all data]

Bartmess and Griffiths, 1990
Bartmess, J.E.; Griffiths, S.S., Tautomerization Energetics of Benzoannelated Toluenes, J. Am. Chem. Soc., 1990, 112, 8, 2932, https://doi.org/10.1021/ja00164a014 . [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]

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]

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]

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]

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 and Lifshitz, 1993
Gotkis, I.; Lifshitz, C., Time-dependent mass spectra and breakdown graphs. 16 - The methylnaphthalenes, Org. Mass Spectrom., 1993, 28, 372. [all data]

Loudon and Mazengo, 1974
Loudon, A.G.; Mazengo, R.Z., Steric strain and electron-impact. The behaviour of some n, n'-dimethyl- 1,1-binaphthyls, some n, n'-dimethylbiphenyls and model compounds, Org. Mass Spectrom., 1974, 8, 179. [all data]

Pitt, Carey, et al., 1972
Pitt, C.G.; Carey, R.N.; Toren, E.C., Nature of the electronic interactions in aryl-substituted polysilanes, J. Am. Chem. Soc., 1972, 94, 3806. [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]

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]

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

Heilbronner, Hornung, et al., 1972
Heilbronner, E.; Hornung, V.; Pinkerton, F.H.; Thames, S.F., 31. Photoelectron spectra of azabenzenes and azanaphthalenes: III. The orbital sequence in methyl- and trimethylsilyl- substituted pyridines, Helv. Chim. Acta, 1972, 55, 289. [all data]

Huang and Dunbar, 1990
Huang, F.-S.; Dunbar, R.C., Time-resolved photodissociation of methylnaphthalene ion. An illustration of kinetic shifts in large-ion dissociations, J. Am. Chem. Soc., 1990, 112, 8167. [all data]

Nounou, 1966
Nounou, P., Etude des composes aromatiques par spectrometrie de masse. I. Mesure des potentials d'ionisation et d'apparition par la methode du potential retardateur et interpretation des courbes d'ionisation differentielle, J. Chim. Phys., 1966, 63, 994. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  S°liquid	Entropy of liquid at standard conditions
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  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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