Bicyclo[1.1.0]butane
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChIKey: LASLVGACQUUOEB-UHFFFAOYSA-N
- CAS Registry Number: 157-33-5
- Chemical structure:
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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 |
---|---|---|---|---|---|
ΔfH°gas | 217. ± 0.8 | kJ/mol | Cm | Wiberg and Fenoglio, 1968 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -2648.7 ± 0.79 | kJ/mol | Cm | Wiberg and Fenoglio, 1968 | Corresponding ΔfHºgas = 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 |
---|---|---|---|---|---|
Tboil | 281.4 | K | N/A | Buckingham 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- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1670. ± 17. | kJ/mol | G+TS | Kass and Chou, 1988 | gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1636. ± 17. | kJ/mol | IMRB | Kass and Chou, 1988 | gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B |
By formula: C4H6I2 = C4H6 + I2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 ± 4.2 | kJ/mol | Cm | Sunner and Wulff, 1973 | liquid 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 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.700 ± 0.005 | PIPECO | Bombach, Dannacher, et al., 1983 | LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3+ | 11.9 ± 0.2 | C2H3 | PI | Bombach, Dannacher, et al., 1983 | LBLHLM |
C3H3+ | 10.1 ± 0.1 | CH3 | PI | Bombach, Dannacher, et al., 1983 | LBLHLM |
C4H4+ | 10.6 ± 0.2 | H2 | PI | Bombach, Dannacher, et al., 1983 | LBLHLM |
C4H5+ | 10.33 ± 0.01 | H | PI | Bombach, Dannacher, et al., 1983 | LBLHLM |
De-protonation reactions
C4H5- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1670. ± 17. | kJ/mol | G+TS | Kass and Chou, 1988 | gas phase; Acidity between NH3, Me2NH, near nPrNH2.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1636. ± 17. | kJ/mol | IMRB | Kass and Chou, 1988 | gas 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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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 |
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, NIST Subscription 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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- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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