Naphthalene, 1-methyl-

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Phase change data

Go To: Top, Gas phase ion energetics data, 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:
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., 1957Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; for sample crystalized rapidly without forming C2; TRC
Ttriple242.6600KN/AMcCullough, Finke, et al., 1957Crystal phase 1 phase; Uncertainty assigned by TRC = 0.03 K; after forming C2 and then C1; TRC
Ttriple242.6900KN/AMcCullough, Finke, et al., 1957Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; after forming C2 and then C1; TRC
Ttriple242.7000KN/AMcCullough, Finke, et al., 1957Crystal 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
Pc35.5 ± 1.atmN/ATsonopoulos and Ambrose, 1995 
Pc35.53atmN/AWilson, Johnston, et al., 1981Uncertainty assigned by TRC = 0.987 atm; TRC
Pc43.0000atmN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 1.5000 atm; TRC
Quantity Value Units Method Reference Comment
Δvap14. ± 2.kcal/molAVGN/AAverage of 8 values; Individual data points

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
12.0500.N/ALee, Dempsey, et al., 1992Based on data from 485. to 595. K.; AC
15.1274.N/ASasse, Jose, et al., 1988Based on data from 259. to 388. K.; AC
13.7293.A,GSStephenson and Malanowski, 1987Based on data from 278. to 313. K. See also Macknick and Prausnitz, 1979.; AC
12.5430.A,GSStephenson and Malanowski, 1987Based on data from 415. to 526. K. See also Camin and Rossini, 1955.; AC
11.9455.N/AWieczorek and Kobayashi, 1981Based on data from 424. to 536. K.; AC
11.0525.N/AWieczorek and Kobayashi, 1981Based on data from 424. to 536. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference
415.29 to 518.484.155111826.948-78.148Camin and Rossini, 1955

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
1.66242.7Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
4.945240.7Domalski and Hearing, 1996CAL
6.840242.7

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.190240.70crystaline, IIcrystaline, IMcCullough, Finke, et al., 1957, 2DH
1.660242.70crystaline, IliquidMcCullough, Finke, et al., 1957, 2DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
4.943240.70crystaline, IIcrystaline, IMcCullough, Finke, et al., 1957, 2DH
6.840242.70crystaline, 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

Go To: Top, Phase change 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)

Quantity Value Units Method Reference Comment
IE (evaluated)7.96 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)199.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity192.5kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
<0.16 ± 0.12ECDWojnarovits and Foldiak, 1981EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.1 eV, anion unbound.; B

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
198.7Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
192.0Aue, 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
7.90 ± 0.02PIGotkis and Lifshitz, 1993LL
8.50 ± 0.05EILoudon and Mazengo, 1974LLK
7.98CTSPitt, Carey, et al., 1972LLK
7.80 ± 0.03EIBonnier, Gelus, et al., 1965RDSH
7.98CTSKinoshita, 1962RDSH
7.96 ± 0.01PIWatanabe, 1957RDSH
8.01 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK
7.95PEHeilbronner, Hornung, et al., 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C11H9+12.1 ± 0.1HTRPIGotkis and Lifshitz, 1993LL
C11H9+10.2 ± 0.2HPIHuang and Dunbar, 1990LL
C11H9+13.2 ± 0.2HEILoudon and Mazengo, 1974LLK
C11H9+12.4 ± 0.1HEINounou, 1966RDSH

De-protonation reactions

C11H9- + Hydrogen cation = Naphthalene, 1-methyl-

By formula: C11H9- + H+ = C11H10

Quantity Value Units Method Reference Comment
Δr374.0 ± 2.1kcal/molG+TSBartmess and Griffiths, 1990gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: ΔG=349.0±2.0, ΔS=27±2, ΔH=357.1; B
Δr370.7 ± 2.5kcal/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
Δr365.8 ± 2.0kcal/molIMREBartmess and Griffiths, 1990gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: ΔG=349.0±2.0, ΔS=27±2, ΔH=357.1; B
Δr362.4 ± 2.0kcal/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

References

Go To: Top, 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.

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]

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]

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]

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]

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]


Notes

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