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Bicyclo[1.1.0]butane

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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
Deltafgas217. ± 0.8kJ/molCmWiberg and Fenoglio, 1968 
Quantity Value Units Method Reference Comment
Deltacgas-2648.7 ± 0.79kJ/molCmWiberg and Fenoglio, 1968Corresponding «DELTA»fgas = 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
Deltar1670. ± 17.kJ/molG+TSKass and Chou, 1988gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B
Quantity Value Units Method Reference Comment
Deltar1636. ± 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
Deltar59.0 ± 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
Deltar1670. ± 17.kJ/molG+TSKass and Chou, 1988gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B
Quantity Value Units Method Reference Comment
Deltar1636. ± 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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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 Chemical Concepts
NIST MS number 151948

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References

Go To: Top, Gas 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.

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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