2,5-Norbornadiene

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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas240. ± 20.kJ/molAVGN/AAverage of 6 values; Individual data points

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
105.60298.15Walsh R., 1975Selected value of S(298.15 K) is in excellent agreement with that calculated by force field method [ Lenz T.G., 1989].; GT
106.36300.
144.47400.
176.36500.
202.00600.
222.80700.
239.95800.
254.35900.
266.481000.

Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid213.8 ± 3.0kJ/molCcbSteele, 1978ALS
Δfliquid178.7 ± 1.0kJ/molCcbHall, Smith, et al., 1973ALS
Quantity Value Units Method Reference Comment
Δcliquid-4111.7 ± 3.0kJ/molCcbSteele, 1978Corresponding Δfliquid = 213.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-4076.7 ± 1.0kJ/molCcbHall, Smith, et al., 1973Corresponding Δfliquid = 178.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-4099.kJ/molCcbSkuratov, Kozina, et al., 1958Corresponding Δfliquid = 201. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
161.2298.15Steele, 1978DH
116.1297.Hall, Smith, et al., 1973DH

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.

Quantity Value Units Method Reference Comment
Tboil362.7KN/AWeast and Grasselli, 1989BS
Tboil363.4KN/ABuckingham and Donaghy, 1982BS
Tboil355.4KN/ATurner, Meador, et al., 1957Uncertainty assigned by TRC = 0.8 K; TRC
Quantity Value Units Method Reference Comment
Tfus254.0KN/ABuckingham and Donaghy, 1982BS
Tfus205.15KN/ABrooks and Pilcher, 1959Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Δvap34. ± 1.kJ/molAVGN/AAverage of 9 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
33.6315.AStephenson and Malanowski, 1987Based on data from 300. to 364. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
1.91255.6Bykova, Smirnova, et al., 2004AC

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

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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
B - John E. Bartmess

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

Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane = 2,5-Norbornadiene

By formula: C7H8 = C7H8

Quantity Value Units Method Reference Comment
Δr-90. ± 30.kJ/molAVGN/AAverage of 6 values; Individual data points

C7H7- + Hydrogen cation = 2,5-Norbornadiene

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Δr1672. ± 7.5kJ/molG+TSLee and Squires, 1986gas phase; Between EtNH2, nPrNH2; B
Quantity Value Units Method Reference Comment
Δr1637. ± 6.3kJ/molIMRBLee and Squires, 1986gas phase; Between EtNH2, nPrNH2; B
Δr1628. ± 21.kJ/molIMRBWright and Beauchamp, 1981gas phase; B

2,5-Norbornadiene + 2Hydrogen = Norbornane

By formula: C7H8 + 2H2 = C7H12

Quantity Value Units Method Reference Comment
Δr-296. ± 1.kJ/molChydDoering, Roth, et al., 1988gas phase; ALS
Δr-291.9 ± 1.5kJ/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane; ALS
Δr-285.0 ± 1.7kJ/molChydTurner, Meador, et al., 1957, 2liquid phase; solvent: Acetic acid; ALS

2,5-Norbornadiene = 1,3-Cyclopentadiene + Acetylene

By formula: C7H8 = C5H6 + C2H2

Quantity Value Units Method Reference Comment
Δr117.2 ± 2.1kJ/molKinWalsh and Wells, 1975gas phase; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 118.7 ± 1.3 kJ/mol; ALS

2,5-Norbornadiene = Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane

By formula: C7H8 = C7H8

Quantity Value Units Method Reference Comment
Δr59. ± 4.kJ/molCisoHarel, Adamson, et al., 1987liquid phase; solvent: Cyclohexane; Photocalorimetry; ALS

1,3-Cyclopentadiene + Acetylene = 2,5-Norbornadiene

By formula: C5H6 + C2H2 = C7H8

Quantity Value Units Method Reference Comment
Δr-117. ± 2.kJ/molEqkWalsh and Wells, 1975gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.

Walsh R., 1975
Walsh R., The enthalpy of formation of bicyclo[2.2.1]hepta-2,5-diene. Thermodynamic functions of bicyclo[2.2.1]heptane and bicyclo[2.2.1]hepta-2,5-diene, J. Chem. Thermodyn., 1975, 7, 149-154. [all data]

Lenz T.G., 1989
Lenz T.G., Force-field calculations giving accurate conformation, Hf(T), S(T), and Cp(T) for unsaturated acyclic and cyclic hydrocarbons, J. Phys. Chem., 1989, 93, 1588-1592. [all data]

Steele, 1978
Steele, W.V., The standard enthalpies of formation of a series of C7, bridged-ring hydrocarbons: norbornane, norbornene, nortricyclene, norbornadiene, and quadricyclane, J. Chem. Thermodyn., 1978, 10, 919-927. [all data]

Hall, Smith, et al., 1973
Hall, H.K., Jr.; Smith, C.D.; Baldt, J.H., Enthalpies of formation of norticyclene, norbornene, norbornadiene, and quadricyclane, J. Am. Chem. Soc., 1973, 95, 3197-3201. [all data]

Skuratov, Kozina, et al., 1958
Skuratov, S.M.; Kozina, M.P.; Shtocher, S.M.; Prevalova, N.M.; Kamkina, L.S.; Zuko, V.D., Heats of combustion of cyclic compounds, Bull. Chem. Thermodyn., 1958, 1, 21. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Winkler, R.E., Heats of Hydrogenation I. Apparatus and the Heats of Hydrogenation of Bicyclo[2.2.1]heptene, Bicyclo[2.2.1]heptadiene, Bicyclo[2.2.2]octene, and Bicyclo[2.2.2]octadiene, J. Am. Chem. Soc., 1957, 79, 4116. [all data]

Brooks and Pilcher, 1959
Brooks, J.H.; Pilcher, G., A Simple Melting Point Calorimeter for Moderately Precise Determination of Purity, J. Chem. Soc., 1959, 1959, 1535. [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]

Bykova, Smirnova, et al., 2004
Bykova, T.A.; Smirnova, N.N.; Nikishchenkova, L.V.; Belov, G.P.; Novikova, E.V., Zh. Fiz. Khim., 2004, 78, 11, 1944. [all data]

Lee and Squires, 1986
Lee, R.E.; Squires, R.R., Anionic homoaromaticity: A gas phase experimental study, J. Am. Chem. Soc., 1986, 105, 5078. [all data]

Wright and Beauchamp, 1981
Wright, C.A.; Beauchamp, J.L., Infrared spectra of gas phase ions and their use in elucidating reaction mechanisms. Identification of C7H7- structural isomers by multiphoton electron detachment using a low-powered laser, J. Am. Chem. Soc., 1981, 103, 6499. [all data]

Doering, Roth, et al., 1988
Doering, W.E.; Roth, W.R.; Breuckmann, R.; Figge, L.; Lennartz, H.-W.; Fessner, W.-D.; Prinzbach, F.H., Verbotene Reaktionen. - [2 + 2]-Cycloreversion starrer Cyclobutane, Chem. Ber., 1988, 121, 1-9. [all data]

Rogers, Choi, et al., 1980
Rogers, D.W.; Choi, L.S.; Girellini, R.S., Heats of hydrogenation and formation of quadricyclene, norbornadiene, norbornene, and nortricyclene, J. Phys. Chem., 1980, 84, 1810-1814. [all data]

Turner, Meador, et al., 1957, 2
Turner, R.B.; Meador, W.R.; Winkler, R.E., Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2,2,1]heptene, bicyclo[2,2,1]heptadiene, bicyclo[2,2,2]octene and bicyclo[2,2,2]octadiene, J. Am. Chem. Soc., 1957, 79, 4116-4121. [all data]

Walsh and Wells, 1975
Walsh, R.; Wells, J.M., The enthalpy of formation of bicyclo[2,2,1]hepta-2,5-diene. Thermodynamic functions of bicyclo[2,2,1]heptane and bicyclo[2,2,1]hepta-2,5-diene, J. Chem. Thermodyn., 1975, 7, 149-154. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Harel, Adamson, et al., 1987
Harel, Y.; Adamson, A.W.; Kutal, C.; Grutsch, P.A.; Yasufuku, K., Photocalorimetry. 6. Enthalpies of isomerization of norbornadiene and of substituted norbornadienes to corresponding quadricyclenes, J. Phys. Chem., 1987, 91, 901-904. [all data]


Notes

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