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Bicyclo[4.2.0]octa-1,3,5-triene


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
Deltafgas199.4 ± 0.9kJ/molCcbRoth, Biermann, et al., 1978 

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

Quantity Value Units Method Reference Comment
Deltafliquid155.7 ± 0.9kJ/molCcbRoth, Biermann, et al., 1978 
Quantity Value Units Method Reference Comment
Deltacliquid-4447.0 ± 0.9kJ/molCcbRoth, Biermann, et al., 1978Corresponding «DELTA»fliquid = 155.6 kJ/mol (simple calculation by NIST; no Washburn corrections)

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
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Deltavap43.7 ± 0.1kJ/molVRoth, Biermann, et al., 1978ALS
Deltavap43.7kJ/molN/ARoth, Biermann, et al., 1978DRB

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
323.6 - 324.0.027Buckingham and Donaghy, 1982BS

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 by: 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

o-Xylylene = Bicyclo[4.2.0]octa-1,3,5-triene

By formula: C8H8 = C8H8

Quantity Value Units Method Reference Comment
Deltar-54.8kJ/molKinRoth and Scholz, 1981gas phase
Deltar-44.2 ± 1.9kJ/molCmRoth, Biermann, et al., 1978liquid phase

C8H8N2O = Nitrous oxide + Bicyclo[4.2.0]octa-1,3,5-triene

By formula: C8H8N2O = N2O + C8H8

Quantity Value Units Method Reference Comment
Deltar-41.2 ± 0.54kJ/molKinOth, Olsen, et al., 1977liquid phase; solvent: THF; At 413 K

3Hydrogen + Bicyclo[4.2.0]octa-1,3,5-triene = Bicyclo[4.2.0]octane

By formula: 3H2 + C8H8 = C8H14

Quantity Value Units Method Reference Comment
Deltar-210.5 ± 0.1kJ/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid

Bicyclo[4.2.0]octa-1,3,5-triene = o-Xylylene

By formula: C8H8 = C8H8

Quantity Value Units Method Reference Comment
Deltar46.4 ± 0.8kJ/molEqkRoth, Ebbrecht, et al., 1988gas phase

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:
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 C8H8+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.74 ± 0.05EIFranklin and Carroll, 1969RDSH
8.66 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK
8.66PEBrogli, Giovannini, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+14.16 ± 0.15?EIFranklin and Carroll, 1969RDSH
C4H2+17.69 ± 0.302C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H3+18.68 ± 0.102C2H2+HEIFranklin and Carroll, 1969RDSH
C4H4+16.01 ± 0.152C2H2EIFranklin and Carroll, 1969RDSH
C5H3+17.34 ± 0.10C2H2+CH3?EIFranklin and Carroll, 1969RDSH
C6H5+15.58 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C6H6+11.55 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C8H6+11.84 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C8H7+11.94 ± 0.10HEIFranklin and Carroll, 1969RDSH

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass 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 AMERICAN OIL CO., WHITING, IND, USA
NIST MS number 34631

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Brovko, et al., 1974
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 16974
Instrument Unicam SP 700
Boiling point 150/ 748 mm

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-Wax1263.Shimoda, Peralta, et al., 199660. m/0.25 mm/0.25 «mu»m, He, 3. K/min; Tstart: 50. C; Tend: 230. C
CapillaryDB-Wax1269.Shimoda, Shigematsu, et al., 199560. m/0.25 mm/0.25 «mu»m, 2. K/min; Tstart: 50. C; Tend: 230. C
CapillaryDB-Wax1258.Sumitani, Suekane, et al., 1994He, 40. C @ 5. min, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySOLGel-Wax1272.Johanningsmeier and McFeeters, 201130. m/0.25 mm/0.25 «mu»m, Helium; Program: 40 0C (2 min) 5 0C/min -> 140 0C 10 0C/min -> 250 0C (3 min)
CapillarySOLGel-Wax1269.Johanningsmeier and McFeeters, 201130. m/0.25 mm/0.25 «mu»m, Helium; Program: not specified

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), UV/Visible spectrum, Gas Chromatography, 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, Biermann, et al., 1978
Roth, W.R.; Biermann, M.; Dekker, H.; Jochems, R.; Mosselman, C.; Hermann, H., Energy profile of the o-quinodimethane-benzocyclobutene equilibrium, Chem. Ber., 1978, 111, 3892-3903. [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]

Roth and Scholz, 1981
Roth, W.R.; Scholz, B.P., Energy profile of the o-quinodimethane = benzocyclobutene equilibrium. Part 2., Chem. Ber., 1981, 114, 3741-3750. [all data]

Oth, Olsen, et al., 1977
Oth, J.F.M.; Olsen, H.; Synder, J.P., Energetics of heteroextrusion reactions. N2 vs. N2O, J. Am. Chem. Soc., 1977, 99, 8505-8507. [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]

Roth, Ebbrecht, et al., 1988
Roth, W.R.; Ebbrecht, T.; Beitat, A., o-Quinodimethane-benzocyclobutene equilibrium: oxygen trapping technique, Chem. Ber., 1988, 121, 1357-1358. [all data]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., The effect of molecular structure on ionic decomposition. I. An electron impact study of seven C8H8 isomers, J. Am. Chem. Soc., 1969, 91, 5940. [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]

Brogli, Giovannini, et al., 1973
Brogli, F.; Giovannini, E.; Heilbronner, E.; Schurter, R., Die photoelektronen spektren der benzocycloalkene, Chem. Ber., 1973, 106, 961. [all data]

Brovko, et al., 1974
Brovko, V.V., et al., Zhur. Organ. Khim., 1974, 10, 2385. [all data]

Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y., Headspace gas analysis of fish sauce, J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u . [all data]

Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion, J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037 . [all data]

Sumitani, Suekane, et al., 1994
Sumitani, H.; Suekane, S.; Nakatani, A.; Tatsuka, K., Changes in composition of volatile compounds in high pressure treated peach, J. Agric. Food Chem., 1994, 42, 3, 785-790, https://doi.org/10.1021/jf00039a037 . [all data]

Johanningsmeier and McFeeters, 2011
Johanningsmeier, S.D.; McFeeters, R.F., Detection of volatile spoilage metabolites in fermented cucumbers using nontargeted, comprehensive 2-dimensional gas chromatography-time-of-flight mass spectrometry (GCxGCxTOFMS), J. Food Sci., 2011, 76, 1, c168-c177, https://doi.org/10.1111/j.1750-3841.2010.01918.x . [all data]


Notes

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