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Naphthalene, 1-methyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas116.9 ± 2.7kJ/molCcbSperos and Rossini, 1960ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
39.150.Thermodynamics Research Center, 1997p=1 bar.; GT
59.1100.
81.1150.
105.9200.
145.6273.15
159.3298.15
160.4300.
212.3400.
256.2500.
291.8600.
320.7700.
344.5800.
364.3900.
381.01000.
395.1100.
407.1200.
418.1300.
426.1400.
434.1500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid56.2 ± 1.7kJ/molCcbSperos and Rossini, 1960ALS
Quantity Value Units Method Reference Comment
Deltacliquid-5783.0 ± 5.8kJ/molCcbBalcan, Arzik, et al., 1996Corresponding «DELTA»fliquid = 25.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-5814.0 ± 1.7kJ/molCcbSperos and Rossini, 1960Corresponding «DELTA»fliquid = 56.27 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-5627.kJ/molCcbHipsher and Wise, 1954«DELTA»Hfusion=2.3 kcal/mol; Corresponding «DELTA»fliquid = -130. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid254.81J/mol*KN/AMcCullough, Finke, et al., 1957DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
224.39298.15McCullough, Finke, et al., 1957T = 10 to 370 K.; DH

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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil515. ± 7.KAVGN/AAverage of 30 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus244. ± 9.KAVGN/AAverage of 27 out of 28 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple242.6600KN/AMcCullough, Finke, et al., 1957, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; for sample crystalized rapidly without forming C2; TRC
Ttriple242.6600KN/AMcCullough, Finke, et al., 1957, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.03 K; after forming C2 and then C1; TRC
Ttriple242.6900KN/AMcCullough, Finke, et al., 1957, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; after forming C2 and then C1; TRC
Ttriple242.7000KN/AMcCullough, Finke, et al., 1957, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.03 K; for sample crystalized rapidly without forming C2; TRC
Quantity Value Units Method Reference Comment
Tc772. ± 1.KN/ATsonopoulos and Ambrose, 1995 
Tc772.KN/AWilson, Johnston, et al., 1981Uncertainty assigned by TRC = 1. K; TRC
Tc772.KN/AAmbrose, 1963Uncertainty assigned by TRC = 1.5 K; TRC
Tc273.15KN/AAmbrose, Cox, et al., 1960Uncertainty assigned by TRC = 2.72 K; Visual, PRT, IPTS-48, rapid decomp and no value obtained sample; TRC
Tc784.0KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc36. ± 1.barN/ATsonopoulos and Ambrose, 1995 
Pc36.00barN/AWilson, Johnston, et al., 1981Uncertainty assigned by TRC = 1.00 bar; TRC
Pc43.5698barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 1.5199 bar; TRC
Quantity Value Units Method Reference Comment
Deltavap59. ± 10.kJ/molAVGN/AAverage of 8 values; Individual data points

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
50.0500.N/ALee, Dempsey, et al., 1992Based on data from 485. - 595. K.; AC
63.3274.N/ASasse, Jose, et al., 1988Based on data from 259. - 388. K.; AC
57.5293.A,GSStephenson and Malanowski, 1987Based on data from 278. - 313. K. See also Macknick and Prausnitz, 1979.; AC
52.3430.A,GSStephenson and Malanowski, 1987Based on data from 415. - 526. K. See also Camin and Rossini, 1955.; AC
49.6455.N/AWieczorek and Kobayashi, 1981Based on data from 424. - 536. K.; AC
45.9525.N/AWieczorek and Kobayashi, 1981Based on data from 424. - 536. 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
415.29 - 518.484.160821826.948-78.148Camin and Rossini, 1955

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
6.95242.7Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
20.69240.7Domalski and Hearing, 1996CAL
28.62242.7

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
4.979240.70crystaline, IIcrystaline, IMcCullough, Finke, et al., 1957DH
6.945242.70crystaline, IliquidMcCullough, Finke, et al., 1957DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
20.68240.70crystaline, IIcrystaline, IMcCullough, Finke, et al., 1957DH
28.62242.70crystaline, IliquidMcCullough, Finke, et al., 1957DH

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:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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

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- + Hydrogen cation = Naphthalene, 1-methyl-

By formula: C11H9- + H+ = C11H10

Quantity Value Units Method Reference Comment
Deltar1565. ± 8.8kJ/molG+TSBartmess and Griffiths, 1990gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: «DELTA»G=349.0±2.0, «DELTA»S=27±2, «DELTA»H=357.1; B
Deltar1551. ± 10.kJ/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
Quantity Value Units Method Reference Comment
Deltar1531. ± 8.4kJ/molIMREBartmess and Griffiths, 1990gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: «DELTA»G=349.0±2.0, «DELTA»S=27±2, «DELTA»H=357.1; B
Deltar1516. ± 8.4kJ/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

C11H10+ + Naphthalene, 1-methyl- = (C11H10+ bullet Naphthalene, 1-methyl-)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar78.7kJ/molPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M
Quantity Value Units Method Reference Comment
Deltar126.J/mol*KPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M

C6H7N+ + Naphthalene, 1-methyl- = (C6H7N+ bullet Naphthalene, 1-methyl-)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar66.1kJ/molPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M
Quantity Value Units Method Reference Comment
Deltar105.J/mol*KPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291511

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

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]

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]

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

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]

Wilson, Johnston, et al., 1981
Wilson, Grant M.; Johnston, Robert H.; Hwang, Shuen-Cheng.; Tsonopoulos, Constantine., Volatility of coal liquids at high temperatures and pressures, Ind. Eng. Chem. Proc. Des. Dev., 1981, 20, 1, 94-104, https://doi.org/10.1021/i200012a015 . [all data]

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

Ambrose, Cox, et al., 1960
Ambrose, D.; Cox, J.D.; Townsend, R., The critical temperatures of forty organic compounds, Trans. Faraday Soc., 1960, 56, 1452. [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]

Lee, Dempsey, et al., 1992
Lee, Chang Ha; Dempsey, Dennis M.; Mohamed, Rahoma S.; Holder, Gerald D., Vapor-liquid equilibria in the systems of n-decane/tetralin, n-hexadecane/tetralin, n-decane/1-methylnaphthalene, and 1-methylnaphthalene/tetralin, J. Chem. Eng. Data, 1992, 37, 2, 183-186, https://doi.org/10.1021/je00006a012 . [all data]

Sasse, Jose, et al., 1988
Sasse, Karim; Jose, Jacques; Merlin, Jean-Claude, A static apparatus for measurement of low vapor pressures. Experimental results on high molecular-weight hydrocarbons, Fluid Phase Equilibria, 1988, 42, 287-304, https://doi.org/10.1016/0378-3812(88)80065-7 . [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]

Macknick and Prausnitz, 1979
Macknick, A. Brian; Prausnitz, John M., Vapor pressures of high-molecular-weight hydrocarbons, J. Chem. Eng. Data, 1979, 24, 3, 175-178, https://doi.org/10.1021/je60082a012 . [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]

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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References