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Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas336.kJ/molChydRoth, Adamczak, et al., 1991 
Deltafgas333.kJ/molChydRogers, Choi, et al., 1980 
Deltafgas339.1 ± 2.3kJ/molCcbSteele, 1978 
Deltafgas325. ± 4.2kJ/molCisoKabakoff, Bunzli, et al., 1975 
Deltafgas253.3 ± 1.1kJ/molCcbHall, Smith, et al., 1973 

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
Deltafliquid302.1 ± 2.2kJ/molCcbSteele, 1978ALS
Deltafliquid216.3 ± 1.1kJ/molCcbHall, Smith, et al., 1973ALS
Quantity Value Units Method Reference Comment
Deltacliquid-4200.0 ± 2.2kJ/molCcbSteele, 1978Corresponding «DELTA»fliquid = 302.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-4114.3 ± 1.1kJ/molCcbHall, Smith, et al., 1973Corresponding «DELTA»fliquid = 216.4 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
157.6298.15Steele, 1978DH
139.1297.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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
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
Deltavap37.3 ± 0.8kJ/molAVGN/AAverage of 8 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
381.20.987Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
37.3 ± 0.8317.BGStephenson and Malanowski, 1987Based on data from 302. - 372. K. See also Hall, Smith, et al., 1973.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
1.09228.Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
40.180.Domalski and Hearing, 1996CAL
4.8228.

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
180.crystaline, IIcrystaline, IKawai, Gilson, et al., 1992S = 40.0 J/mol*K; DH
228.crystaline, IliquidKawai, Gilson, et al., 1992S = 4.8 J/mol*K; 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:
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
Deltar-90. ± 30.kJ/molAVGN/AAverage of 6 values; Individual data points

C7H7- + Hydrogen cation = Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Deltar1686. ± 4.2kJ/molD-EAGunion, Karney, et al., 1996gas phase; Assignment of 1- and 2- isomers uncertain.; B
Deltar1685.6 ± 3.8kJ/molG+TSLee, DePuy, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar1651.4 ± 3.3kJ/molIMRELee, DePuy, et al., 1996gas phase; B

2Hydrogen + Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane = Norbornane

By formula: 2H2 + C7H8 = C7H12

Quantity Value Units Method Reference Comment
Deltar-384.7 ± 1.8kJ/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane; ALS
Deltar-385.1 ± 2.1kJ/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid; ALS

C7H7- + Hydrogen cation = Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Deltar1685.7 ± 3.8kJ/molG+TSLee, DePuy, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar1651.4 ± 3.3kJ/molIMRELee, DePuy, et al., 1996gas phase; B

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

By formula: C7H8 = C7H8

Quantity Value Units Method Reference Comment
Deltar59. ± 4.kJ/molCisoHarel, Adamson, et al., 1987liquid phase; solvent: Cyclohexane; Photocalorimetry; ALS

Gas phase ion energetics 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
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 C7H8+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
7.8PEMartin, Heller, et al., 1974LLK
8.70EIDolejsek, Hanus, et al., 1962RDSH
8.33PEMartin, Heller, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+9.56HEIDolejsek, Hanus, et al., 1962RDSH

De-protonation reactions

C7H7- + Hydrogen cation = Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Deltar1686. ± 4.2kJ/molD-EAGunion, Karney, et al., 1996gas phase; Assignment of 1- and 2- isomers uncertain.; B
Deltar1685.6 ± 3.8kJ/molG+TSLee, DePuy, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar1651.4 ± 3.3kJ/molIMRELee, DePuy, et al., 1996gas phase; B

C7H7- + Hydrogen cation = Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Deltar1685.7 ± 3.8kJ/molG+TSLee, DePuy, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar1651.4 ± 3.3kJ/molIMRELee, DePuy, et al., 1996gas phase; B

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, NIST Free Links, 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

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-7278
NIST MS number 237789

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), NIST Free Links, Notes

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

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [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]

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]

Kabakoff, Bunzli, et al., 1975
Kabakoff, D.S.; Bunzli, J.-C.G.; Oth, J.F.M.; Hammond, W.B.; Berson, J.A., Enthalpy and kinetics of isomerization of quadricyclane to norbornadiene. Strain energy of quadricyclane, J. Am. Chem. Soc., 1975, 97, 1510-1511. [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]

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]

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]

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]

Kawai, Gilson, et al., 1992
Kawai, N.T.; Gilson, D.F.R.; Butler, I.S., The order-disorder phase transition in the cage hydrocarbon quadricyclane, Mol. Cryst. Liq. Cryst. Sci. Technol., Sect., 1992, A 211, 59-61. [all data]

Gunion, Karney, et al., 1996
Gunion, R.F.; Karney, W.; Wenthold, P.G.; Borden, W.T.; Lineberger, W.C., Ultraviolet Photoelectron Spectroscopy of Some C7H7- Isomers: Quadricyclanide, Norbornadienide, Cycloheptatrienide, and 1,6-Heptadiynide, J. Am. Chem. Soc., 1996, 118, 21, 5074, https://doi.org/10.1021/ja954026f . [all data]

Lee, DePuy, et al., 1996
Lee, H.S.; DePuy, C.H.; Bierbaum, V.M., Reactivity and Thermochemistry of Quadricyclane in the Gas Phase, J. Am. Chem. Soc., 1996, 118, 21, 5068, https://doi.org/10.1021/ja9540278 . [all data]

Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M., Heats of hydrogenation. VIII. Compounds with three- and four-membered rings, J. Am. Chem. Soc., 1968, 90, 4315-4322. [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]

Martin, Heller, et al., 1974
Martin, H.-D.; Heller, C.; Haselbach, E.; Lanyjova, Z., 49. Quadricyclanes. Part I: Photoelectron spectra and electronic structure, Helv. Chim. Acta, 1974, 57, 465. [all data]

Dolejsek, Hanus, et al., 1962
Dolejsek, Z.; Hanus, V.; Prinzbach, H., Das massenspektrometrische Verhalten von Quadricyclen, Angew. Chem., 1962, 74, 902. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), NIST Free Links, References