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:
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • 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)

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Phase change data

Go To: Top, Gas phase ion energetics data, 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Entropy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

Entropy of sublimation

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

Go To: Top, Phase change data, 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 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 C₁₀H₈⁺ (ion structure unspecified)

Electron affinity determinations

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₁₀H₇^- +  =

By formula: C₁₀H₇^- + H⁺ = C₁₀H₈

C₁₀H₇^- +  =

By formula: C₁₀H₇^- + H⁺ = C₁₀H₈

Mass spectrum (electron ionization)

Go To: Top, Phase change data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Phase change data, Gas phase ion energetics data, 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.

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]

Cheng, 1963
Cheng, D.C.H., Critical temperatures and volumes of some binary systems, Chem. Eng. Sci., 1963, 18, 715. [all data]

Chirico, Knipmeyer, et al., 1993
Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Steele, W.V., The thermodynamic properties to the temperature 700 K of naphthalene and of 2,7-dimethylnaphthalene, J. Chem. Thermodyn., 1993, 25, 1461-94. [all data]

Schroeer, 1941
Schroeer, E., Critical State VI. Vapor-pressure Curve of Naphthalene Up To the Critical Point, Z. Phys. Chem., Abt. B, 1941, 49, 271-8. [all data]

Zhuravlev, 1937
Zhuravlev, D.I., Crit. Temp. and Orthobaric Density of Diphenyl Ether and Napphthalene naphthalene, Zh. Fiz. Khim., 1937, 9, 875. [all data]

Zhao, Unhannanant, et al., 2008
Zhao, Hui; Unhannanant, Patamaporn; Hanshaw, William; Chickos, James S., Enthalpies of Vaporization and Vapor Pressures of Some Deuterated Hydrocarbons. Liquid-Vapor Pressure Isotope Effects, J. Chem. Eng. Data, 2008, 53, 7, 1545-1556, https://doi.org/10.1021/je800091s . [all data]

Haftka, Parsons, et al., 2006
Haftka, Joris J.H.; Parsons, John R.; Govers, Harrie A.J., Supercooled liquid vapour pressures and related thermodynamic properties of polycyclic aromatic hydrocarbons determined by gas chromatography, Journal of Chromatography A, 2006, 1135, 1, 91-100, https://doi.org/10.1016/j.chroma.2006.09.050 . [all data]

Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul, Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements, Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2 . [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Torres-Gomez, Barreiro-Rodriguez, et al., 1988
Torres-Gomez, L.A.; Barreiro-Rodriguez, G.; Galarza-Mondragon, A., A new method for the measurement of enthalpies of sublimation using differential scanning calorimetry, Thermochim. Acta, 1988, 124, 229-233. [all data]

Lei, Chankalal, et al., 2002
Lei, Ying Duan; Chankalal, Raymond; Chan, Anita; Wania, Frank, Supercooled Liquid Vapor Pressures of the Polycyclic Aromatic Hydrocarbons, J. Chem. Eng. Data, 2002, 47, 4, 801-806, https://doi.org/10.1021/je0155148 . [all data]

Boller and Wiedemann, 1998
Boller, A.; Wiedemann, H.G., Journal of Thermal Analysis and Calorimetry, 1998, 53, 2, 431-439, https://doi.org/10.1023/A:1010133106907 . [all data]

Back, Grzyll, et al., 1996
Back, Dwight D.; Grzyll, Lawrence R.; Corrigan, Mary, DSC enthalpy of vaporization measurements of high temperature two-phase working fluids, Thermochimica Acta, 1996, 272, 53-63, https://doi.org/10.1016/0040-6031(95)02615-0 . [all data]

Chirico, Knipmeyer, et al., 1993, 2
Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Steele, W.V., The thermodynamic properties to the temperature 700 K of naphthalene and of 2,7-dimethylnaphthalene, J. Chem. Thermodyn., 1993, 25, 1461-1494. [all data]

Lee and Holder, 1993
Lee, Chang Ha; Holder, Gerald D., Vapor-liquid equilibria in the systems toluene/naphthalene and cyclohexane/naphthalene, J. Chem. Eng. Data, 1993, 38, 2, 320-323, https://doi.org/10.1021/je00010a034 . [all data]

Ambrose, Ewing, et al., 1990
Ambrose, D.; Ewing, M.B.; Ghiassee, N.B.; Sanchez Ochoa, J.C., The ebulliometric method of vapour-pressure measurement: vapour pressures of benzene, hexafluorobenzene, and naphthalene, The Journal of Chemical Thermodynamics, 1990, 22, 6, 589-605, https://doi.org/10.1016/0021-9614(90)90151-F . [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]

de Kruif, Kuipers, et al., 1981
de Kruif, C.G.; Kuipers, T.; van Miltenburg, J.C.; Schaake, R.C.F.; Stevens, G., The vapour pressure of solid and liquid naphthalene, The Journal of Chemical Thermodynamics, 1981, 13, 11, 1081-1086, https://doi.org/10.1016/0021-9614(81)90006-9 . [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]

Fowler, Trump, et al., 1968
Fowler, Lewis.; Trump, Walter N.; Vogler, Carl E., Vapor pressure of naphthalene. Measurements between 40.deg. and 180.deg., J. Chem. Eng. Data, 1968, 13, 2, 209-210, https://doi.org/10.1021/je60037a020 . [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]

Barrow and McClellan, 1951
Barrow, Gordon M.; McClellan, A.L., The Thermodynamic Properties of Naphthalene, J. Am. Chem. Soc., 1951, 73, 2, 573-575, https://doi.org/10.1021/ja01146a020 . [all data]

Cramer, 1943
Cramer, K.S.N., Chem. Zentr. II, 1943, 2234. [all data]

Mortimer and Murphy, 1923
Mortimer, F. Spencer.; Murphy, Ray v., The Vapor Pressures of Some Substances Found in Coal Tar., Ind. Eng. Chem., 1923, 15, 11, 1140-1142, https://doi.org/10.1021/ie50167a012 . [all data]

NELSON and SENSEMAN, 1922
NELSON, O.A.; SENSEMAN, C.E., Vapor Pressure Determinations on Naphthalene, Anthracene, Phecanthrene, and Anthraquinone between Their Melting and Boiling Points, J. Ind. Eng. Chem., 1922, 14, 1, 58-62, https://doi.org/10.1021/ie50145a028 . [all data]

Grayson and Fosbraey, 2006
Grayson, B. Terence; Fosbraey, Lynda A., Determination of the vapour pressure of pesticides, Pestic. Sci., 2006, 13, 3, 269-278, https://doi.org/10.1002/ps.2780130308 . [all data]

McEachern and Sandoval, 2001
McEachern, D.M.; Sandoval, O., A molecular flow evaporation apparatus for measuring vapour pressures and heats of sublimation of organic compounds, J. Phys. E: Sci. Instrum., 2001, 6, 2, 155-161, https://doi.org/10.1088/0022-3735/6/2/026 . [all data]

Nass, Lenoir, et al., 1995
Nass, Karen; Lenoir, Dieter; Kettrup, Antonius, Calculation of the Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons by an Incremental Procedure, Angew. Chem. Int. Ed. Engl., 1995, 34, 16, 1735-1736, https://doi.org/10.1002/anie.199517351 . [all data]

Wania, Shiu, et al., 1994
Wania, Frank; Shiu, Wan-Ying; Mackay, Donald, Measurement of the Vapor Pressure of Several Low-Volatility Organochlorine Chemicals at Low Temperatures with a Gas Saturation Method, J. Chem. Eng. Data, 1994, 39, 3, 572-577, https://doi.org/10.1021/je00015a039 . [all data]

Khudyakov, 1988
Khudyakov, V.L., Russ. J. Phys. Chem., 1988, 62, 1743. [all data]

SATO, INOMATA, et al., 1986
SATO, NOBUYUKI; INOMATA, HIROSHI; ARAI, KUNIO; SAITO, SHOZABURO, Measurement of vapor pressures for coal-related aromatic compounds by gas saturation method., J. Chem. Eng. Japan / JCEJ, 1986, 19, 2, 145-147, https://doi.org/10.1252/jcej.19.145 . [all data]

Glukhova, Arkhangelova, et al., 1985
Glukhova, O.T.; Arkhangelova, N.M.; Teplitsky, A.B.; Sukhodub, L.F.; Yanson, I.K.; Kaminski, Miron, The low-temperature quartz resonator method for determination of the enthalpy of sublimation, Thermochimica Acta, 1985, 95, 1, 133-138, https://doi.org/10.1016/0040-6031(85)80041-1 . [all data]

Matsubara and Kuwamoto, 1985
Matsubara, Norio; Kuwamoto, Tooru, Vapor pressure measurements in carrier gas containing ligand vapor using the transpiration technique, Thermochimica Acta, 1985, 83, 2, 193-202, https://doi.org/10.1016/0040-6031(85)87003-9 . [all data]

Sonnefeld, Zoller, et al., 1983
Sonnefeld, W.J.; Zoller, W.H.; May, W.E., Dynamic coupled-column liquid-chromatographic determination of ambient-temperature vapor pressures of polynuclear aromatic hydrocarbons, Anal. Chem., 1983, 55, 2, 275-280, https://doi.org/10.1021/ac00253a022 . [all data]

Colomina, Jimenez, et al., 1982
Colomina, M.; Jimenez, P.; Turrion, C., Vapour pressures and enthalpies of sublimation of naphthalene and benzoic acid, J. Chem. Thermodyn., 1982, 14, 779-784. [all data]

Kruif, 1980
Kruif, C.G., Enthalpies of sublimation and vapour pressures of 11 polycyclic hydrocarbons, J. Chem. Thermodyn., 1980, 12, 243-248. [all data]

Murray, Cavell, et al., 1980
Murray, J.P.; Cavell, K.J.; Hill, J.O., A DSC study of benzoic acid: a suggested calibrant compound, Thermochimica Acta, 1980, 36, 1, 97-101, https://doi.org/10.1016/0040-6031(80)80114-6 . [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]

De Kruif and Van Ginkel, 1977
De Kruif, C.G.; Van Ginkel, C.H.D., Torsion-weighing effusion vapour-pressure measurements on organic compounds, The Journal of Chemical Thermodynamics, 1977, 9, 8, 725-730, https://doi.org/10.1016/0021-9614(77)90015-5 . [all data]

Ambrose, Lawrenson, et al., 1975
Ambrose, D.; Lawrenson, I.J.; Sprake, C.H.S., The vapour pressure of naphthalene, The Journal of Chemical Thermodynamics, 1975, 7, 12, 1173-1176, https://doi.org/10.1016/0021-9614(75)90038-5 . [all data]

Chickos, 1975
Chickos, James Speros, A simple equilibrium method for determining heats of sublimation, J. Chem. Educ., 1975, 52, 2, 134-39, https://doi.org/10.1021/ed052p134 . [all data]

McEachern, Sandoval, et al., 1975
McEachern, D.M.; Sandoval, O.; Iniguez, J.C., Vapor pressures, derived enthalpies of sublimation, enthalpies of fusion, and resonance energies of acridine and phenazine, J. Chem. Thermodyn., 1975, 7, 299-306. [all data]

Radchenko and Kitaigorodskii, 1974
Radchenko, L.G.; Kitaigorodskii, A.I., The vapour pressures and heats of sublimation of naphthalene, biphenyl, octafluoronaphthalene, decafluorobiphenyl, acenaphthene and α-nitronaphthalene, Russ. J. Phys. Chem. (Engl. Transl.), 1974, 48, 1595. [all data]

Radchenko, 1971
Radchenko, L.G., Zh. Fiz. Khim., 1971, 45, 5, 1310. [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]

Miller, 1963
Miller, George A., Vapor Pressure of Naphthalene. Thermodynamic Consistency with Proposed Frequency Assignments., J. Chem. Eng. Data, 1963, 8, 1, 69-72, https://doi.org/10.1021/je60016a019 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Aihara, 1959
Aihara, A., Estimation of the energy of hydrogen bonds formed in crystals. I. Sublimation pressures of some organic molecular crystals and the additivity of lattice energy, Bull. Chem. Soc. Jpn., 1959, 32, 1242. [all data]

Aihara, 1959, 2
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. I. Sublimation Pressures of Some Organic Molecular Crystals and the Additivity of Lattice Energy, Bull. Chem. Soc. Jpn., 1959, 32, 11, 1242-1248, https://doi.org/10.1246/bcsj.32.1242 . [all data]

Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W., Z. Elektrochem., 1958, 62, 61. [all data]

Sklyarenko, Markin, et al., 1958
Sklyarenko, S.I.; Markin, B.I.; Belyaeva, L.B., Zh. Fiz. Khim., 1958, 32, 1916. [all data]

Sherwood and Bryant, 1957
Sherwood, T.K.; Bryant, J.H., Jr., Can. J. Chem. Eng., 1957, 35, 51. [all data]

Bradley and Cleasby, 1953
Bradley, R.S.; Cleasby, T.G., 346. The vapour pressure and lattice energy of hydrogen-bonded crystals. Part I. Oxamide, oxamic acid, and rubeanic acid, J. Chem. Soc., 1953, 1681, https://doi.org/10.1039/jr9530001681 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Sears and Hopke, 1954
Sears, G.W.; Hopke, E.R., The Vapor Pressure of Naphthalene, J. Am. Chem. Soc., 1954, 76, 7, 2026-2026, https://doi.org/10.1021/ja01636a099 . [all data]

Bradley and Cleasby, 1953, 2
Bradley, R.S.; Cleasby, T.G., The vapour pressure and lattice energy of some aromatic ring compounds, J. Am. Chem. Soc., 1953, 1690-16. [all data]

Zibberman-Granovskaya, 1940
Zibberman-Granovskaya, A.A., Russ. J. Phys. Chem., 1940, 14, 759. [all data]

Andrews, 1925
Andrews, Mary R., Vapor Pressure of Naphthalene at Low Temperatures, J. Phys. Chem., 1925, 30, 11, 1497-1500, https://doi.org/10.1021/j150269a005 . [all data]

Swan and Mack, 1925
Swan, Thomas H.; Mack, Edward, VAPOR PRESSURES OF ORGANIC CRYSTALS BY AN EFFUSION METHOD, J. Am. Chem. Soc., 1925, 47, 8, 2112-2116, https://doi.org/10.1021/ja01685a005 . [all data]

Mastrangelo, 1957
Mastrangelo, S.V.R., Adiabatic calorimeter for determination of cryoscopic data, Anal. Chem., 1957, 29(5), 841-845. [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]

Spaght, Thomas, et al., 1932
Spaght, M.E.; Thomas, S.B.; Parks, G.S., Some heat capacity data on organic compounds obtained with a radiation calorimeter, J. Phys. Chem., 1932, 36, 882-888. [all data]

Sharma, Gupta, et al., 2008
Sharma, B.L.; Gupta, S.; Tandon, S.; Kant, R., Physico-mechanical properties of naphthalene--acenaphthene eutectic system by different modes of solidification, Materials Chemistry and Physics, 2008, 111, 2-3, 423-430, https://doi.org/10.1016/j.matchemphys.2008.04.049 . [all data]

Hafsaoui and Mahmoud, 2007
Hafsaoui, S.L.; Mahmoud, R., Solid-liquid equilibria of binary systems containing n-tetracosane with naphthalene or dibenzofuran, J Therm Anal Calorim, 2007, 88, 2, 565-570, https://doi.org/10.1007/s10973-006-8084-2 . [all data]

Khimeche and Dahmani, 2006
Khimeche, Kamel; Dahmani, Abdallah, Solid-Liquid Equilibria of Naphthalene + Alkanediamine Mixtures, J. Chem. Eng. Data, 2006, 51, 2, 382-385, https://doi.org/10.1021/je0502851 . [all data]

Khimeche and Dahmani, 2006, 2
Khimeche, K.; Dahmani, A., Determination by DSC of solid--liquid diagrams for polyaromatic -- 4,4'diaminodiphenylmethane binary systems, J Therm Anal Calorim, 2006, 84, 1, 47-52, https://doi.org/10.1007/s10973-005-7167-9 . [all data]

Chirico, Knipmeyer, et al., 2002
Chirico, R.D.; Knipmeyer, S.E.; Steele, W.V., Heat capacities, enthalpy increments, and derived thermodynamic functions for naphthalene between the temperatures 5K and 440K, The Journal of Chemical Thermodynamics, 2002, 34, 11, 1873-1884, https://doi.org/10.1016/S0021-9614(02)00262-8 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Syunyaev, Tumanyan, et al., 1984
Syunyaev, Z.I.; Tumanyan, B.P.; Kolesnikov, S.I.; Zhokhova, N.I., Some anomalies in melting points of binary mixtures of solid hydrocarbons, Zhur. Prikl. Khim. (Leningrad), 1984, 57, 666-669. [all data]

Rastogi and Bassi, 1964
Rastogi, R.P.; Bassi, P.S., Mechanism of eutectic crystallization, J. Phys. Chem., 1964, 68, 2398-2406. [all data]

Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J., Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme, Z. Natursforsch. 5a, 1950, 101-108. [all data]

Eibert, 1944
Eibert, J., Thesis Washington University (St. Louis), 1944. [all data]

Schmidt, 1941
Schmidt, W.R., Thesis Washington University (St. Louis), 1941. [all data]

Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J., The heat capacities and heat of crystallization of some isomeric aromatic compounds, J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]

David, 1964
David, D.J., Determination of specific heat and heat of fusion by differential thermal analysis. Study of theory and operating parameters, Anal. Chem., 1964, 36, 2162-2166. [all data]

Andon and Connett, 1980
Andon, R.J.L.; Connett, J.E., Calibrants for thermal analysis. Measurement of their enthalpies of fusion by adiabatic calorimetry, Thermochim. Acta, 1980, 42, 241-247. [all data]

Radomska and Radomski, 1980
Radomska, M.; Radomski, R., Calorimetric studies of binary systems of 1,3,5-trinitrobenzene with naphthalene, anthracene, and carbazole. I. Phase transitions and heat capacities of the pure components and charge-transfer complexes, Thermochim. Acta, 1980, 40, 405-414. [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]

Lyapustina, Xu, et al., 2000
Lyapustina, S.A.; Xu, S.K.; Nilles, J.M.; Bowen, K.H., Solvent-induced stabilization of the naphthalene anion by water molecules: A negative cluster ion photoelectron spectroscopic study, J. Chem. Phys., 2000, 112, 15, 6643-6648, https://doi.org/10.1063/1.481237 . [all data]

Song, Han, et al., 2002
Song, J.K.; Han, S.Y.; Chu, I.H.; Kim, J.H.; Kim, S.K.; Lyapustina, S.A.; Xu, S.J.; Nilles, J.M.; Bowen, K.H., Photoelectron spectroscopy of naphthalene cluster anions, J. Chem. Phys., 2002, 116, 11, 4477-4481, https://doi.org/10.1063/1.1449869 . [all data]

Schiedt, Knott, et al., 2000
Schiedt, J.; Knott, W.J.; Le Barbu, K.; Schlag, E.W.; Weinkauf, R., Microsolvation of similar-sized aromatic molecules: Photoelectron spectroscopy of bithiophene-, azulene-, and naphthalene-water anion clusters, J. Chem. Phys., 2000, 113, 21, 9470-9478, https://doi.org/10.1063/1.1319874 . [all data]

Burrow, Michejda, et al., 1987
Burrow, P.D.; Michejda, J.A.; Jordan, K.D., Electron Transmission Study of the Temporary Negative Ion States of Selected Benzenoid and Conjugated Aromatic Hydrocarbons., J. Chem. Phys., 1987, 86, 1, 9, https://doi.org/10.1063/1.452598 . [all data]

Zlatkis, Lee, et al., 1983
Zlatkis, A.; Lee, C.K.; Wentworth, W.E.; Chen, E.C.M., Constant current linearization for determination of electron capture mechanisms, Anal. Chem., 1983, 55, 1596. [all data]

Heinis, Chowdhury, et al., 1993
Heinis, T.; Chowdhury, S.; Kebarle, P., Electron Affinities of Naphthalene, Anthracene and Substituted Naphthalenes and Anthracenes, Org. Mass Spectrom., 1993, 28, 4, 358, https://doi.org/10.1002/oms.1210280416 . [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]

Becker and Chen, 1966
Becker, R.S.; Chen, E., Extension of Electron Affinities and Ionization Potentials of Aromatic Hydrocarbons, J. Chem. Phys., 1966, 45, 7, 2403, https://doi.org/10.1063/1.1727954 . [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, Oleinikova, et al., 1993
Gotkis, Y.; Oleinikova, M.; Naor, M.; Lifshitz, C., Time-independent mass spectra and breakdown graphs. 17. Naphthalene and phenanthrene, J. Phys. Chem., 1993, 97, 12282. [all data]

Cockett, Ozeki, et al., 1993
Cockett, M.C.R.; Ozeki, H.; Okuyama, K.; Kimura, K., Vibronic coupling in the ground cationic state of naphthalene: A laser threshold photoelectron [zero kinetic energy (ZEKE)-photoelectron] spectroscopic study, J. Chem. Phys., 1993, 98, 7763. [all data]

Jochims, Rasekh, et al., 1992
Jochims, H.-W.; Rasekh, H.; Ruhl, E.; Baumgartel, H.; Leach, S., The photofragmentation of naphthalene and azulene monocations in the energy range 7-22 eV, Chem. Phys., 1992, 168, 159. [all data]

Stahl and Maquin, 1984
Stahl, D.; Maquin, F., Charge-stripping mass spectrometry of molecular ions from polyacenes and molecular orbital theory, Chem. Phys. Lett., 1984, 108, 613. [all data]

Duncan, Dietz, et al., 1981
Duncan, M.A.; Dietz, T.G.; Smalley, R.E., Two-color photoionization of naphthalene and benzene at threshold, J. Chem. Phys., 1981, 75, 2118. [all data]

Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M., Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite, J. Phys. Chem., 1980, 84, 2716. [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]

Schafer, Schweig, et al., 1973
Schafer, W.; Schweig, A.; Markl, G.; Heier, K.-H., Zur elektronenstruktur der lambda₃- und lambda₅-phosphanaphthaline--ungewohnlich grosse MO destabilisierungen, Tetrahedron Lett., 1973, 3743. [all data]

Pitt, 1973
Pitt, C.G., Hyperconjugation and its role in group IV chemistry, J. Organomet. Chem., 1973, 61, 49. [all data]

Clark, Brogli, et al., 1972
Clark, P.A.; Brogli, F.; Heilbronner, E., The π-orbital energies of the acenes, Helv. Chim. Acta, 1972, 55, 1415. [all data]

Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A., Perfluoro effect in photoelectron spectroscopy. II. Aromatic molecules, J. Am. Chem. Soc., 1972, 94, 1466. [all data]

Brogli, Heilbronner, et al., 1972
Brogli, F.; Heilbronner, E.; Kobayashi, T., Photoelectron spectra of azabenzenes and azanaphthalenes: II. A reinvestigation of azanaphthalenes by high-resolution photoelectron spectroscopy, Helv. Chim. Acta, 1972, 55, 274. [all data]

Johnstone, Mellon, et al., 1970
Johnstone, R.A.W.; Mellon, F.A.; Ward, S.D., Online acquisition of ionization efficiency data, Intern. J. Mass Spectrom. Ion Phys., 1970, 5, 241. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Yencha and El-Sayed, 1968
Yencha, A.J.; El-Sayed, M.A., Lowest ionization potentials of some nitrogen heterocyclics, J. Chem. Phys., 1968, 48, 3469. [all data]

Kitagawa, 1968
Kitagawa, T., Absorption spectra and photoionization of polycyclic aromatics in vacuum ultraviolet region, J. Mol. Spectry., 1968, 26, 1. [all data]

Eland and Danby, 1968
Eland, J.H.D.; Danby, C.J., Inner ionization potentials of aromatic compounds, Z. Naturforsch., 1968, 23a, 355. [all data]

Angus, Christ, et al., 1968
Angus, J.G.; Christ, B.J.; Morris, G.C., Absorption spectra in the vacuum ultraviolet and the ionization potentials of naphthalene and naphthalene-d, molecules, Australian J. Chem., 1968, 21, 2153. [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]

Kuroda, 1964
Kuroda, H., Ionization potentials of polycyclic aromatic hydrocarbons, Nature, 1964, 201, 1214. [all data]

Briegleb, 1964
Briegleb, G., Electron affinity of organic molecules, Angew. Chem. Intern. Ed., 1964, 3, 617. [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]

Terenin, 1961
Terenin, A., Charge transfer in organic solids, induced by light, Proc. Chem. Soc., London, 1961, 321. [all data]

Birks and Stifkin, 1961
Birks, J.B.; Stifkin, M.A., π-Electronic excitation and ionization energies of condensed ring aromatic hydrocarbons, Nature, 1961, 191, 761. [all data]

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

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [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]

Kaim, Tesmann, et al., 1980
Kaim, W.; Tesmann, H.; Bock, H., Me₃C-, Me₃Si-, Me₃Ge-, Me₃Sn- und Me₃Pb-substituierte benzol- und naphthalin-derivate und ihre radikalanionen, Chem. Ber., 1980, 113, 3221. [all data]

Schmidt, 1977
Schmidt, W., Photoelectron spectra of polynuclear aromatics. V. Correlations with ultraviolet absorption spectra in the catacondensed series, J. Chem. Phys., 1977, 66, 828. [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]

Clar and Schmidt, 1976
Clar, E.; Schmidt, W., Correlations between photoelectron and phosphorescence spectra of polycyclic hydrocarbons, Tetrahedron, 1976, 32, 2563. [all data]

Marschner and Goetz, 1974
Marschner, F.; Goetz, H., Korrelation zwischen photoelektronen- und elektronen-spektren. II. Untersuchung aromatischer π-systeme mit modifizierten PPP-SCF-CI-parametern, Tetrahedron, 1974, 30, 3159. [all data]

Bock, Wagner, et al., 1972
Bock, H.; Wagner, G.; Kroner, J., Photoelektronenspektren und molekuleigenschaften, XIV. Die delokalisation des schwefel-elektronenpaar in CH₃S-substituierten aromaten, Chem. Ber., 1972, 105, 3850. [all data]

Bock and Wagner, 1972
Bock, H.; Wagner, G., Electron lone pairs in organic sulfides and disulfides, Angew. Chem. Int. Ed. Engl., 1972, 11, 119. [all data]

Jochims, Rasekh, et al., 1993
Jochims, H.-W.; Rasekh, H.; Ruhl, E.; Baumgartel, H.; Leach, S., Deuterium isotope effects in the photofragmentation of naphthalene monocations, J. Phys. Chem., 1993, 97, 1312. [all data]

VanBrunt and Wacks, 1964
VanBrunt, R.J.; Wacks, M.E., Electron-impact studies of aromatic hydrocarbons. III. Azulene and naphthalene, J. Chem. Phys., 1964, 41, 3195. [all data]

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]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔsubS	Entropy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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