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Naphthalene

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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:
DRB - Donald R. Burgess, Jr.
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
Deltafgas150. ± 10.kJ/molAVGN/AAverage of 7 values; Individual data points

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
36.1850.Thermodynamics Research Center, 1997p=1 bar. Selected values of S(T) and Cp(T) agree with those calculated by statistical thermodynamics method [ Dorofeeva O.V., 1986, Dorofeeva O.V., 1988] within 1.2 J/mol*K. Discrepancies with other calculations [ Barrow G.M., 1951, McClellan A.L., 1955, 79CHE/KUD, Lielmezs J., 1981] reach 2-3 J/mol*K.; GT
47.50100.
63.89150.
84.99200.
120.52273.15
133.02298.15
133.94300.
181.16400.
220.70500.
252.37600.
277.77700.
298.43800.
315.50900.
329.771000.
341.81100.
352.01200.
360.81300.
368.21400.
374.71500.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
201.6 ± 2.0451.0Barrow G.M., 1951GT
226.7 ± 2.3522.7

Condensed phase thermochemistry data

Go To: Top, Gas 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 compiled as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
liquid217.59J/mol*KN/AChirico, Knipmeyer, et al., 1993DH
Quantity Value Units Method Reference Comment
Deltafsolid77. ± 10.kJ/molAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltacsolid-5160. ± 20.kJ/molAVGN/AAverage of 18 values; Individual data points
Quantity Value Units Method Reference Comment
solid,1 bar167.40J/mol*KN/AMcCullough, Finke, et al., 1957DH
solid,1 bar162.84J/mol*KN/ASouthard and Brickwedde, 1933DH
solid,1 bar166.86J/mol*KN/APearce and Tanner, 1934Extrapolation below 90 K, 58.32 J/mol*K.; DH
solid,1 bar166.9J/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 53.09 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
196.06298.15Chirico, Knipmeyer, et al., 1993T = 260 to 700 K.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
213.330.David, 1964T = 298 to 353 K. Mean value. T = uncertain.; DH
188.4342.Rastogi and Bassi, 1964T = 342, 384 K.; DH
165.69298.15McCullough, Finke, et al., 1957T = 10 to 370 K.; DH
156.1298.15Ueberreiter and Orthmann, 1950T = 293 to 368 K. Equation only.; DH
195.8298.1Eibert, 1944T = 30 to 200°C, equations only in t°C. Cp(c) = 0.365 cal/g*K (30 to 80°C); Cp(liq) = 0.329 + 0.000824t cal/g*K (80 to 200°C).; DH
161.5298.1Schmidt, 1941T = 22 to 200°C, equations only, in t°C. Cp(c) = 0.2595 + 0.001672t cal/g*K (22 to 80°C); Cp(liq) = 0.3360 + 0.0008180t cal/g*K (80 to 200°C).; DH
168.11301.58Hicks, 1938T = 58 to 304 K. Value is unsmoothed experimental datum.; DH
168.07297.6Pearce and Tanner, 1934T = 94 to 298 K. Value is unsmoothed experimental datum.; DH
165.48294.68Southard and Brickwedde, 1933T = 15 to 295 K. Value is unsmoothed experimental datum.; DH
169.0303.Spaght, Thomas, et al., 1932T = 30 to 190°C.; DH
163.6295.1Huffman, Parks, et al., 1930T = 91 to 295 K.; DH
159.4298.Andrews, Lynn, et al., 1926T = 12 to 300°C.; DH

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C10H7- + Hydrogen cation = Naphthalene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Deltar1649. ± 5.0kJ/molBranReed and Kass, 2000gas phase; B
Deltar1649. ± 5.0kJ/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
Deltar1648. ± 21.kJ/molCIDCLardin, Squires, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Deltar1613. ± 5.4kJ/molH-TSReed and Kass, 2000gas phase; B
Deltar1606. ± 5.0kJ/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
Deltar1613. ± 21.kJ/molH-TSLardin, Squires, et al., 2001gas phase; B

C6H7N+ + Naphthalene = (C6H7N+ bullet Naphthalene)

By formula: C6H7N+ + C10H8 = (C6H7N+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar64.4kJ/molPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar110.J/mol*KN/AEl-Shall and Meot-Ner (Mautner), 1987gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
31.324.PHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; Entropy change calculated or estimated; M

C12H8+ + Naphthalene = (C12H8+ bullet Naphthalene)

By formula: C12H8+ + C10H8 = (C12H8+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar52.7kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar120.J/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar21.kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

C12H9+ + Naphthalene = (C12H9+ bullet Naphthalene)

By formula: C12H9+ + C10H8 = (C12H9+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar58.2kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar120.J/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar27.kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

2Hydrogen + Naphthalene = Naphthalene, 1,2,3,4-tetrahydro-

By formula: 2H2 + C10H8 = C10H12

Quantity Value Units Method Reference Comment
Deltar-125.kJ/molEqkFrye and Weitkamp, 1969gas phase; ALS
Deltar-120.5 ± 5.0kJ/molEqkWilson, Caflisch, et al., 1958gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -133.9 ± 5.0 kJ/mol; At 400 K; ALS

Benzobicyclo[2.2.0]hexa-2,5-diene = Naphthalene

By formula: C10H8 = C10H8

Quantity Value Units Method Reference Comment
Deltar-248.5 ± 8.0kJ/molEqkDreeskamp, Kapahnke, et al., 1988liquid phase; solvent: Heptane; Isomerization; ALS
Deltar-249.2 ± 8.0kJ/molCisoGrimme and Heinze, 1978liquid phase; solvent: Heptane; ALS

C10H8+ + Naphthalene = (C10H8+ bullet Naphthalene)

By formula: C10H8+ + C10H8 = (C10H8+ bullet C10H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar74.5kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase; M
Quantity Value Units Method Reference Comment
Deltar120.J/mol*KPHPMSMeot-Ner (Mautner), 1980gas phase; M

C10H7- + Hydrogen cation = Naphthalene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Deltar1655. ± 5.4kJ/molBranReed and Kass, 2000gas phase; B
Quantity Value Units Method Reference Comment
Deltar1619. ± 5.9kJ/molH-TSReed and Kass, 2000gas phase; B

H4O4- + Naphthalene + 2Water = C10H12O4-

By formula: H4O4- + C10H8 + 2H2O = C10H12O4-

Quantity Value Units Method Reference Comment
Deltar219. ± 9.6kJ/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

H2O3- + Naphthalene + Water = C10H10O3-

By formula: H2O3- + C10H8 + H2O = C10H10O3-

Quantity Value Units Method Reference Comment
Deltar158. ± 9.6kJ/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

C10H9+ + Naphthalene = (C10H9+ bullet Naphthalene)

By formula: C10H9+ + C10H8 = (C10H9+ bullet C10H8)

Quantity Value Units Method Reference Comment
Deltar59.0kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase; M
Quantity Value Units Method Reference Comment
Deltar130.J/mol*KPHPMSMeot-Ner (Mautner), 1980gas phase; M

Oxygen anion + Naphthalene = C10H8O2-

By formula: O2- + C10H8 = C10H8O2-

Quantity Value Units Method Reference Comment
Deltar92.5 ± 9.6kJ/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

Nitric oxide anion + Naphthalene = C10H8NO-

By formula: NO- + C10H8 = C10H8NO-

Quantity Value Units Method Reference Comment
Deltar60.7 ± 9.6kJ/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

C10H8NO- + 2Naphthalene = C20H16NO-

By formula: C10H8NO- + 2C10H8 = C20H16NO-

Quantity Value Units Method Reference Comment
Deltar99.6 ± 9.6kJ/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

5Hydrogen + Naphthalene = Naphthalene, decahydro-, cis-

By formula: 5H2 + C10H8 = C10H18

Quantity Value Units Method Reference Comment
Deltar-318.kJ/molEqkFrye and Weitkamp, 1969gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

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]

Dorofeeva O.V., 1986
Dorofeeva O.V., On calculation of thermodynamic properties of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1986, 102, 59-66. [all data]

Dorofeeva O.V., 1988
Dorofeeva O.V., Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons in the Gaseous Phase. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-238 (in Russian), Moscow, 1988. [all data]

Barrow G.M., 1951
Barrow G.M., The thermodynamic properties of naphthalene, J. Am. Chem. Soc., 1951, 73, 573-575. [all data]

McClellan A.L., 1955
McClellan A.L., Vibrational assignment and thermodynamic properties of naphthalene, J. Chem. Phys., 1955, 23, 245-248. [all data]

Lielmezs J., 1981
Lielmezs J., Jr., Thermodynamic functions for naphthalene, Thermochim. Acta, 1981, 47, 287-308. [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, 1461-1494. [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]

Southard and Brickwedde, 1933
Southard, J.C.; Brickwedde, F.G., Low temperature specific heats. I. An improved calorimeter for use from 14 to 300 K. The heat capacity and entropy of naphthalene. J. Am. Chem. Soc., 1933, 4378-4384. [all data]

Pearce and Tanner, 1934
Pearce, J.N.; Tanner, W.B., The heat capacity and the free energy of formation of naphthalene, Proc. Iowa Acad. Sci., 1934, 41, 123-126. [all data]

Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-1558. [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]

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]

Hicks, 1938
Hicks, J.F.G., Jr., A low temperature calorimeter. The heat capacity and entropy of thallium from 14 to 300°K. Low temperature studies. No. 3, J. Am. Chem. Soc., 1938, 60, 1000-1004. [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]

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]

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]

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]

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [all data]

Frye and Weitkamp, 1969
Frye, C.G.; Weitkamp, A.W., Equilibrium hydrogenations of multi-ring aromatics, J. Chem. Eng. Data, 1969, 14, 372-376. [all data]

Wilson, Caflisch, et al., 1958
Wilson, T.P.; Caflisch, E.G.; Hurley, G.F., The naphthalene-tetralin-hydrogen equilibrium at elevated temperature and pressure, J. Phys. Chem., 1958, 62, 1059. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Dreeskamp, Kapahnke, et al., 1988
Dreeskamp, H.; Kapahnke, P.; Tochtermann, W., Photo valence isomerization of sterically strained aromatic hydrocarbons: 8,9-dicarbethoxy[6]paracyclophane, Radiat. Phys. Chem., 1988, 32, 537-539. [all data]

Grimme and Heinze, 1978
Grimme, W.; Heinze, U., Kinetics and enthalpy of isomerization of benzobicyclo[2.2.0]hexa-2,5-diene, Chem. Ber., 1978, 111, 2563-2570. [all data]

Le Barbu, Schiedt, et al., 2002
Le Barbu, K.; Schiedt, J.; Weinkauf, R.; Schlag, E.W.; Nilles, J.M.; Xu, S.J.; Thomas, O.C.; Bowen, K.H., Microsolvation of small anions by aromatic molecules: An exploratory study, J. Chem. Phys., 2002, 116, 22, 9663-9671, https://doi.org/10.1063/1.1475750 . [all data]


Notes

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