Naphthalene, 2-methyl-

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Gas 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas116.1 ± 2.6kJ/molCcbSperos and Rossini, 1960Hfusion=2.83±0.01; ALS
Δfgas106.2kJ/molN/ARichardson and Parks, 1939Value computed using ΔfHsolid° value of 35.0±2.2 kj/mol from Richardson and Parks, 1939 and ΔsubH° value of 71.2 kj/mol from Richardson and Parks, 1939.; DRB

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
43.350.Thermodynamics Research Center, 1997p=1 bar.; GT
61.9100.
80.8150.
103.2200.
141.1273.15
154.6298.15
155.6300.
207.7400.
252.2500.
288.5600.
318.0700.
342.3800.
362.5900.
379.41000.
394.1100.
406.1200.
417.1300.
426.1400.
433.1500.

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tboil514. ± 1.KAVGN/AAverage of 15 out of 16 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus307. ± 1.KAVGN/AAverage of 15 out of 16 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple307.7200KN/AMcCullough, Finke, et al., 1957Crystal phase 1 phase; Uncertainty assigned by TRC = 0.08 K; TRC
Ttriple307.7200KN/AMcCullough, Finke, et al., 1957Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple307.2KN/AHuffman, Parks, et al., 1931Uncertainty assigned by TRC = 0.25 K; TRC
Quantity Value Units Method Reference Comment
Tc761. ± 1.KN/ATsonopoulos and Ambrose, 1995 
Tc761.15KN/AAmbrose, 1963Uncertainty assigned by TRC = 1.5 K; TRC
Tc764.55KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc32.9306barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 1.5199 bar; TRC
Quantity Value Units Method Reference Comment
Δvap45.31kJ/molCGlaser and Ruland, 1957ALS
Quantity Value Units Method Reference Comment
Δsub65.69 ± 0.84kJ/molCSabbah, Chastel, et al., 1974ALS
Δsub71.3 ± 2.1kJ/molVSperos and Rossini, 1960Hfusion=2.83±0.01; ALS
Δsub71.2kJ/molN/ASperos and Rossini, 1960DRB

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
51.2438.A,GSStephenson and Malanowski, 1987Based on data from 423. to 515. K. See also Camin and Rossini, 1955.; AC
48.4465.N/AWieczorek and Kobayashi, 1981Based on data from 424. to 535. K.; AC
46.4505.N/AWieczorek and Kobayashi, 1981Based on data from 424. to 535. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference
412.34 to 514.914.19341840.268-74.755Camin and Rossini, 1955

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
61.71 ± 0.84283.VKaryakin, Rabinovich, et al., 1968ALS

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
12.13307.7Domalski and Hearing, 1996AC
11.966307.2Huffman, Parks, et al., 1931, 2DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
39.0307.2Huffman, Parks, et al., 1931, 2DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
19.43288.5Domalski and Hearing, 1996CAL
39.43307.7

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
5.606288.5crystaline, IIcrystaline, IMcCullough, Finke, et al., 1957, 2DH
12.125307.73crystaline, IliquidMcCullough, Finke, et al., 1957, 2DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
19.43288.5crystaline, IIcrystaline, IMcCullough, Finke, et al., 1957, 2DH
39.40307.73crystaline, IliquidMcCullough, Finke, et al., 1957, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics 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 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 C11H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)7.91 ± 0.06eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)831.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity802.4kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
<0.143 ± 0.069ECDWojnarovits and Foldiak, 1981EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.2 eV, anion unbound.; B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
830.9Aue, 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
802.1Aue, 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
7.91 ± 0.02TRPIGotkis and Lifshitz, 1993LL
7.8PEKlasinc, Kovac, et al., 1983LBLHLM
7.83PESchafer, Schweig, et al., 1975LLK
8.45 ± 0.05EILoudon and Mazengo, 1974LLK
8.10 ± 0.03EIBonnier, Gelus, et al., 1965RDSH
7.96 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
7.85PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
7.93PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
8.01 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK
7.93PEHeilbronner, Hornung, et al., 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C11H9+13.2 ± 0.2HEILoudon and Mazengo, 1974LLK
C11H9+13.2 ± 0.2HEINounou, 1966RDSH

De-protonation reactions

C11H9- + Hydrogen cation = Naphthalene, 2-methyl-

By formula: C11H9- + H+ = C11H10

Quantity Value Units Method Reference Comment
Δr1559. ± 8.8kJ/molG+TSAntol, Glasovac, et al., 2003gas phase; B
Quantity Value Units Method Reference Comment
Δr1528. ± 8.4kJ/molIMREAntol, Glasovac, et al., 2003gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Phase change 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]

Richardson and Parks, 1939
Richardson, J.W.; Parks, G.S., Thermal data on organic compounds. XIX. Modern combustion data for some non-volatile compounds containing carbon, hydrogen and oxygen, J. Am. Chem. Soc., 1939, 61, 3543-3546. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

McCullough, Finke, et al., 1957
McCullough, J.P.; Finke, H.L.; Messerly, J.F.; Todd, S.S.; Kincheloe, T.C.; Waddington, G., The Low-Temperature Thermodynamic Properties of Naphthalene, 1-Methylnaphthalene, 2-Methylnaphthalene, 1,2,3,4-tetrahydro- naphthalene, trans-decahydronaphthalene and cis-Decahydronaphthalene, J. Phys. Chem., 1957, 61, 1105. [all data]

Huffman, Parks, et al., 1931
Huffman, H.M.; Parks, G.S.; Barmore, M., Thermal Data on Organic Compounds X. Further Studies on the Heat Capacities, Entropies, and Free Energies of Hydrocarbons, J. Am. Chem. Soc., 1931, 53, 3876-88. [all data]

Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons, J. Chem. Eng. Data, 1995, 40, 547-558. [all data]

Ambrose, 1963
Ambrose, D., Critical Temperatures of Some Phenols and Other Organic Compounds, Trans. Faraday Soc., 1963, 59, 1988. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Sabbah, Chastel, et al., 1974
Sabbah, R.; Chastel, R.; Laffitte, M., Thermochemical study of methyl naphthalenes, Thermochim. Acta, 1974, 10, 353-358. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Camin and Rossini, 1955
Camin, David L.; Rossini, Frederick D., Physical Properties of Fourteen API Research Hydrocarbons, C 9 to C 15, J. Phys. Chem., 1955, 59, 11, 1173-1179, https://doi.org/10.1021/j150533a014 . [all data]

Wieczorek and Kobayashi, 1981
Wieczorek, Stefan A.; Kobayashi, Riki, Vapor-pressure measurements of 1-methylnaphthalene, 2-methylnaphthalene, and 9,10-dihydrophenanthrene at elevated temperatures, J. Chem. Eng. Data, 1981, 26, 1, 8-11, https://doi.org/10.1021/je00023a005 . [all data]

Karyakin, Rabinovich, et al., 1968
Karyakin, N.V.; Rabinovich, I.B.; Pakhomov, L.G., Heats of sublimation of naphthalene and its monosubstituted β-derivatives, Russ. J. Phys. Chem. (Engl. Transl.), 1968, 42, 954. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Huffman, Parks, et al., 1931, 2
Huffman, H.M.; Parks, G.S.; Barmore, M., Thermal data on organic compounds. X. Further studies on the heat capacities, entropies and free energies of hydrocarbons, J. Am. Chem. Soc., 1931, 53, 3876-3888. [all data]

McCullough, Finke, et al., 1957, 2
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]

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]

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]

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]

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]

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]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]

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]

Antol, Glasovac, et al., 2003
Antol, I.; Glasovac, Z.; Hare, M.C.; Eckert-Maksic, M.; Kass, S.R., On the acidity of cyclopropanaphthalenes - Gas phase and computational studies, Int. J. Mass Spectrom., 2003, 222, 1-3, 11-26, https://doi.org/10.1016/S1387-3806(02)00953-3 . [all data]


Notes

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