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Cyclobutane, methylene-

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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 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
Deltafgas106.kJ/molChydRoth, Adamczak, et al., 1991ALS
Deltafgas121.5 ± 0.71kJ/molCcbGood, Moore, et al., 1974ALS
Quantity Value Units Method Reference Comment
gas298.9 ± 1.0J/mol*KN/AFinke H.L., 1981Close 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
87.40298.15Andreevskii D.N., 1976GT
87.99300.
118.41400.
144.98500.
166.90600.
185.06700.
200.29800.
213.22900.
224.261000.

Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid93.85 ± 0.59kJ/molCcbGood, Moore, et al., 1974ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3204.7 ± 0.50kJ/molCcbGood, Moore, et al., 1974Corresponding «DELTA»fliquid = 93.85 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid210.2J/mol*KN/AFinke, Messerly, et al., 1981DH
liquid210.6J/mol*KN/ALebedev, Tsvetkova, et al., 1978DH
liquid210.6J/mol*KN/ALebedev, Tsvetkova, et al., 1978, 2DH
liquid210.6J/mol*KN/ALebedev, Lebedev, et al., 1975DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
131.1298.15Finke, Messerly, et al., 1981T = 12 to 301 K. Equation also given for temperature range 146 to 301 K.; DH
133.6298.15Lebedev, Tsvetkova, et al., 1978T = 12 to 315 K.; DH
133.6298.15Lebedev, Tsvetkova, et al., 1978, 2T = 12 to 315 K.; DH
133.6298.15Lebedev, Lebedev, et al., 1975T = 6 to 320 K.; DH

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 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
Tboil314. ± 4.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus138.47KN/ASlabey, 1946Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Ttriple138.530KN/AFinke, Messerly, et al., 1981, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.005 K; TRC
Ttriple138.62KN/ALebedev, Tsvetkova, et al., 1978, 3Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Deltavap27.7 ± 0.42kJ/molEGood, Moore, et al., 1974ALS
Deltavap27.7kJ/molN/AGood, Moore, et al., 1974DRB
Deltavap27.7 ± 0.4kJ/molEBGood, Moore, et al., 1974AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
315.20.999Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
26.1303.AStephenson and Malanowski, 1987Based on data from 290. - 316. K.; AC
29.1299.AStephenson and Malanowski, 1987Based on data from 292. - 306. K. See also Lebedev, Tsvetkova, et al., 1978, 2 and Lebedev, Tsvetkova, et al., 1978, 4.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
5.755138.62Lebedev, Tsvetkova, et al., 1978DH
5.755138.62Lebedev, Tsvetkova, et al., 1978, 2DH
5.756138.621Lebedev, Lebedev, et al., 1975DH
5.86138.5Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
41.6138.62Lebedev, Tsvetkova, et al., 1978DH
41.6138.62Lebedev, Tsvetkova, et al., 1978, 2DH
41.6138.621Lebedev, Lebedev, et al., 1975DH

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
5.8614138.535crystaline, IliquidFinke, Messerly, et al., 1981DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
42.31138.535crystaline, IliquidFinke, Messerly, et al., 1981DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

C5H7- + Hydrogen cation = Cyclobutane, methylene-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Deltar1620. ± 21.kJ/molG+TSGuo and Kass, 1992gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Deltar1586. ± 21.kJ/molIMRBGuo and Kass, 1992gas phase; Between H2O, MeOH; B

Cyclobutane, methylene- + Hydrogen = Cyclobutane, methyl-

By formula: C5H8 + H2 = C5H10

Quantity Value Units Method Reference Comment
Deltar-123.1 ± 0.3kJ/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid; 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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C5H8+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.19 ± 0.02PEBieri, Burger, et al., 1977LLK
9.14 ± 0.08EIPuttemans and Delvaux, 1973LLK
9.12PEDemeo and Yencha, 1970RDSH
9.16 ± 0.02PIDemeo and El-Sayed, 1970RDSH
9.35PEWiberg, Ellison, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+14.09 ± 0.15C2H4+HEIPuttemans and Delvaux, 1973LLK
C3H4+11.71 ± 0.10C2H4EIPuttemans and Delvaux, 1973LLK
C4H5+11.23 ± 0.08CH3EIPuttemans and Delvaux, 1973LLK
C5H7+10.64 ± 0.10HEIPuttemans and Delvaux, 1973LLK

De-protonation reactions

C5H7- + Hydrogen cation = Cyclobutane, methylene-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Deltar1620. ± 21.kJ/molG+TSGuo and Kass, 1992gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Deltar1586. ± 21.kJ/molIMRBGuo and Kass, 1992gas phase; Between H2O, MeOH; 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 Japan AIST/NIMC Database- Spectrum MS-IW-1088
NIST MS number 227746

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Loeffler and Pickett, 1958
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 12964
Instrument n.i.g.
Melting point - 134.7
Boiling point 41-42/ 739 mm

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-127.536.Heberger, 199025. m/0.25 mm/0.50 «mu»m, He
CapillaryOV-130.546.Heberger, 199025. m/0.25 mm/0.50 «mu»m, He
PackedSqualane27.534.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.536.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.537.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.539.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH535.White, Hackett, et al., 1992100. m/0.25 mm/0.5 «mu»m, He, 1. K/min; Tstart: 30. C; Tend: 220. C

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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]

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, 345-355. [all data]

Lebedev, Tsvetkova, et al., 1978
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, 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, 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]

Slabey, 1946
Slabey, V.A., J. Am. Chem. Soc., 1946, 68, 1335. [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. [all data]

Lebedev, Tsvetkova, et al., 1978, 3
Lebedev, B.V.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of methylenecyclobutane, J. Chem. Thermodyn., 1978, 10, 809-15. [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, 4
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]

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]

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]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Puttemans and Delvaux, 1973
Puttemans, J.-P.; Delvaux, J.C., Ionisation et fragmentation d'isomeres C5H8 sous impact electronique. Spiropentane - methylenecyclobutane - isoprene, Ing. Chim. Brussell, 1973, 55(267-8), 7. [all data]

Demeo and Yencha, 1970
Demeo, D.A.; Yencha, A.J., Photoelectron spectra of bicyclic and exocyclic olefins, J. Chem. Phys., 1970, 53, 4536. [all data]

Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A., Ionization potential and structure of olefins, J. Chem. Phys., 1970, 52, 2622. [all data]

Wiberg, Ellison, et al., 1976
Wiberg, K.B.; Ellison, G.B.; Wendoloski, J.J.; Brundle, C.R.; Kuebler, N.A., Electronic states of organic molecules. 3. Photoelectron spectra of cycloalkenes and methylenecycloalkanes, J. Am. Chem. Soc., 1976, 98, 7179. [all data]

Loeffler and Pickett, 1958
Loeffler, B.; Pickett, L., J. Chem. Phys., 1958, 28, 345. [all data]

Heberger, 1990
Heberger, K., Identification of C5H8 Isomers Through Reactions of Singlet Methylene, CH21A1), 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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References