Cyclobutane, methylene-
- Formula: C5H8
- Molecular weight: 68.1170
- 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
View 3d structure (requires JavaScript / HTML 5) - Species with the same structure:
- Other names: Methylenecyclobutane
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Phase change data
Go To: Top, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 314. ± 4. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 138.47 | K | N/A | Slabey, 1946 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 138.530 | K | N/A | Finke, Messerly, et al., 1981 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.005 K; TRC |
Ttriple | 138.62 | K | N/A | Lebedev, Tsvetkova, et al., 1978 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 6.62 ± 0.10 | kcal/mol | E | Good, Moore, et al., 1974 | ALS |
ΔvapH° | 6.62 | kcal/mol | N/A | Good, Moore, et al., 1974 | DRB |
ΔvapH° | 6.62 ± 0.1 | kcal/mol | EB | Good, Moore, et al., 1974 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
315.2 | 0.986 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.24 | 303. | A | Stephenson and Malanowski, 1987 | Based on data from 290. to 316. K.; AC |
6.96 | 299. | A | Stephenson and Malanowski, 1987 | Based on data from 292. to 306. K. See also Lebedev, Tsvetkova, et al., 1978, 2 and Lebedev, Tsvetkova, et al., 1978, 3.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.375 | 138.62 | Lebedev, Tsvetkova, et al., 1978, 4 | DH |
1.375 | 138.62 | Lebedev, Tsvetkova, et al., 1978, 2 | DH |
1.376 | 138.621 | Lebedev, Lebedev, et al., 1975 | DH |
1.40 | 138.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.94 | 138.62 | Lebedev, Tsvetkova, et al., 1978, 4 | DH |
9.94 | 138.62 | Lebedev, Tsvetkova, et al., 1978, 2 | DH |
9.94 | 138.621 | Lebedev, Lebedev, et al., 1975 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.4009 | 138.535 | crystaline, I | liquid | Finke, Messerly, et al., 1981, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
10.11 | 138.535 | crystaline, I | liquid | Finke, Messerly, et al., 1981, 2 | DH |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Slabey, 1946
Slabey, V.A.,
J. Am. Chem. Soc., 1946, 68, 1335. [all data]
Finke, Messerly, et al., 1981
Finke, H.L.; Messerly, J.F.; Lee-Bechtold, S.H.,
Thermodynamic properties of cyclopropylamine,cyclopentylamine,and methylenecyclobutane,
J. Chem. Thermodyn., 1981, 13, 345. [all data]
Lebedev, Tsvetkova, et al., 1978
Lebedev, B.V.; Tsvetkova, L.Ya.; Rabinovich, I.B.,
Thermodynamics of methylenecyclobutane,
J. Chem. Thermodyn., 1978, 10, 809-15. [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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Lebedev, Tsvetkova, et al., 1978, 2
Lebedev, B.V.; Tsvetkova, L.Ya.; Rabinovich, I.B.,
Thermodynamics of methylenecyclobutane,
J. Chem. Thermodyn., 1978, 10, 809-815. [all data]
Lebedev, Tsvetkova, et al., 1978, 3
Lebedev, B.V.; Tsvetkova, L.Y.; Rabinovich, I.B.; Finkel'shtein, E.S.; Strel'chick, B.S.,
Termodin. Org. Soedin., 1978, 7, 3. [all data]
Lebedev, Tsvetkova, et al., 1978, 4
Lebedev, B.V.; Tsvetkova, L.Ya.; Rabinovich, I.B.; Finkel'shtein, E.Sh.; Strel'chik, B.S.,
Thermodynamic characteristics of methylenecyclobutane,
Termodin. Org. Soedin., 1978, (7), 3-7. [all data]
Lebedev, Lebedev, et al., 1975
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, Y.G.; Tsvetkova, L.Ya.; Rabinovich, I.B.,
Thermodynamics of methylenecyclobutane and 1,5-cyclooctadiene,
Quatrieme Conference International de Thermodynamique Chimique, 1975, II, Thermophysique (capacites thermiques) pp. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Finke, Messerly, et al., 1981, 2
Finke, H.L.; Messerly, J.F.; Lee-Bechtold, S.H.,
Thermodynamic properties of cyclopropylamine, cyclopentylamine, and methylenecyclobutane,
J. Chem. Thermodyn., 1981, 13, 345-355. [all data]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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