Bicyclo[1.1.0]butane


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
Δfgas217. ± 0.8kJ/molCmWiberg and Fenoglio, 1968 
Quantity Value Units Method Reference Comment
Δcgas-2648.7 ± 0.79kJ/molCmWiberg and Fenoglio, 1968Corresponding Δfgas = 217.1 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 by: Robert L. Brown and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil281.4KN/ABuckingham and Donaghy, 1982 

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
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

C4H5- + Hydrogen cation = Bicyclo[1.1.0]butane

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Δr1670. ± 17.kJ/molG+TSKass and Chou, 1988gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B
Quantity Value Units Method Reference Comment
Δr1636. ± 17.kJ/molIMRBKass and Chou, 1988gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B

1,3-Diiodocyclobutane = Bicyclo[1.1.0]butane + Iodine

By formula: C4H6I2 = C4H6 + I2

Quantity Value Units Method Reference Comment
Δr59.0 ± 4.2kJ/molCmSunner and Wulff, 1973liquid phase; 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C4H6+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.70 ± 0.01eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
8.700 ± 0.005PIPECOBombach, Dannacher, et al., 1983LBLHLM

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3+11.9 ± 0.2C2H3PIBombach, Dannacher, et al., 1983LBLHLM
C3H3+10.1 ± 0.1CH3PIBombach, Dannacher, et al., 1983LBLHLM
C4H4+10.6 ± 0.2H2PIBombach, Dannacher, et al., 1983LBLHLM
C4H5+10.33 ± 0.01HPIBombach, Dannacher, et al., 1983LBLHLM

De-protonation reactions

C4H5- + Hydrogen cation = Bicyclo[1.1.0]butane

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Δr1670. ± 17.kJ/molG+TSKass and Chou, 1988gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B
Quantity Value Units Method Reference Comment
Δr1636. ± 17.kJ/molIMRBKass and Chou, 1988gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B

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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Additional Data

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Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Chemical Concepts
NIST MS number 151948

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References

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

Wiberg and Fenoglio, 1968
Wiberg, K.B.; Fenoglio, R.A., Heats of formation of C4H6 hydrocarbons, J. Am. Chem. Soc., 1968, 90, 3395-3397. [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]

Kass and Chou, 1988
Kass, S.R.; Chou, P.K., The Bicyclobutyl Anion: An Alkyl Carbanion, J. Am. Chem. Soc., 1988, 110, 23, 7899, https://doi.org/10.1021/ja00231a063 . [all data]

Sunner and Wulff, 1973
Sunner, S.; Wulff, C.A., Ring strain in diiodocyclobutane, Acta Chem. Scand., 1973, 27, 315-317. [all data]

Bombach, Dannacher, et al., 1983
Bombach, R.; Dannacher, J.; Stadelmann, J.-P.; Neier, R., Fundamental aspects of ionic dissociations: The fragmentation pathways of excited bicyclobutane cations, Helv. Chim. Acta, 1983, 66, 701. [all data]


Notes

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