1,3,5-Cycloheptatriene

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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

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Individual Reactions

3Hydrogen + 1,3,5-Cycloheptatriene = Cycloheptane

By formula: 3H2 + C7H8 = C7H14

Quantity Value Units Method Reference Comment
Δr-72.8 ± 0.1kcal/molChydRoth, Klaerner, et al., 1983liquid phase; solvent: Isooctane; ALS
Δr-70.49 ± 0.39kcal/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid; ALS
Δr-72.11 ± 0.30kcal/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -72.85 ± 0.01 kcal/mol; at 355 K; ALS

C7H7- + Hydrogen cation = 1,3,5-Cycloheptatriene

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Δr375.2 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr369.2 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

Norcaradiene = 1,3,5-Cycloheptatriene

By formula: C7H8 = C7H8

Quantity Value Units Method Reference Comment
Δr0.160kcal/molEqkGorlitz and Gunther, 1969liquid phase; NMR; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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

Roth, Klaerner, et al., 1983
Roth, W.R.; Klaerner, F.G.; Gerit, F.; Grimme, W.; Koeser, H.G.; Busch, R.; Muskulus, B.; Breuckmann, R.; Scholz, B.P.; Lennartz, H.W., Stereochemistry of the bicyclo[2.1.0]pentane ring opening: thermolysis of tricyclo[3.2.0.0(,)]heptane derivatives, Chem. Ber., 1983, 116, 2717-2737. [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, 4116-4121. [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Gorlitz and Gunther, 1969
Gorlitz, M.; Gunther, H., Protonenresonanz-spektroskopie ungesattigter ringsysteme-XIII, Tetrahedron, 1969, 25, 4467-4480. [all data]


Notes

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