Cyclobutane, methylene-
- Formula: C5H8
- Molecular weight: 68.1170
- IUPAC Standard InChI: InChI=1S/C5H8/c1-5-3-2-4-5/h1-4H2
- IUPAC Standard InChIKey: QIRVGKYPAOQVNP-UHFFFAOYSA-N
- CAS Registry Number: 1120-56-5
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Species with the same structure:
- Other names: Methylenecyclobutane
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas Chromatography, References, Notes
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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 106. | kJ/mol | Chyd | Roth, Adamczak, et al., 1991 | ALS |
| ΔfH°gas | 121.5 ± 0.71 | kJ/mol | Ccb | Good, Moore, et al., 1974 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 298.9 ± 1.0 | J/mol*K | N/A | Finke H.L., 1981 | Close value of S(298.15 K)=298.6(1.7) J/mol*K was calculated by [ Andreevskii D.N., 1983] using other value for the entropy of the liquid state.; GT |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 87.40 | 298.15 | Andreevskii D.N., 1976 | GT |
| 87.99 | 300. | ||
| 118.41 | 400. | ||
| 144.98 | 500. | ||
| 166.90 | 600. | ||
| 185.06 | 700. | ||
| 200.29 | 800. | ||
| 213.22 | 900. | ||
| 224.26 | 1000. |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas Chromatography, References, Notes
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
C5H7- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1620. ± 21. | kJ/mol | G+TS | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1586. ± 21. | kJ/mol | IMRB | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
+
=
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -123.1 ± 0.3 | kJ/mol | Chyd | Turner, Goebel, et al., 1968 | liquid phase; solvent: Acetic acid; ALS |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | OV-1 | 27. | 536. | Heberger, 1990 | 25. m/0.25 mm/0.50 μm, He |
| Capillary | OV-1 | 30. | 546. | Heberger, 1990 | 25. m/0.25 mm/0.50 μm, He |
| Packed | Squalane | 27. | 534. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 49. | 536. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 67. | 537. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 86. | 539. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Petrocol DH | 535. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas Chromatography, 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]
Good, Moore, et al., 1974
Good, W.D.; Moore, R.T.; Osborn, A.G.; Douslin, D.R.,
The enthalpies of formation of ethylcyclobutane, methylenecyclobutane, and 1,1-dimethylcyclopropane,
J. Chem. Thermodyn., 1974, 6, 303-310. [all data]
Finke H.L., 1981
Finke H.L.,
Thermodynamic properties of cyclopropylamine, cyclopentylamine, and methylenecyclobutane,
J. Chem. Thermodyn., 1981, 13, 345-355. [all data]
Andreevskii D.N., 1983
Andreevskii D.N.,
Value of the S(298.15) entropy of methylenecyclobutane in the gaseous state,
Zh. Fiz. Khim., 1983, 57, 2109. [all data]
Andreevskii D.N., 1976
Andreevskii D.N.,
The similar structures method in thermodynamics of C3-C5 methylenecycloalkanes,
Zh. Strukt. Khim., 1976, 17, 51-57. [all data]
Guo and Kass, 1992
Guo, H.Z.; Kass, S.R.,
Vinylcyclopropyl Anion - Structure, Reactivity, Thermodynamic Properties, and an Unusual Rearrangement,
J. Am. Chem. Soc., 1992, 114, 4, 1244, https://doi.org/10.1021/ja00030a019
. [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]
Heberger, 1990
Heberger, K.,
Identification of C5H8 Isomers Through Reactions of Singlet Methylene, CH2(ã1A1), with Unsaturated Hydrocarbons Using Capillary Gas Chromatography - Mass Spectrometry,
Analyst, 1990, 115, 6, 725-729, https://doi.org/10.1039/an9901500725
. [all data]
Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203
. [all data]
White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas S°gas Entropy 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.