Cyclobutane

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 phase ion energetics data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, 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: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
34.1550.Dorofeeva O.V., 1986Discrepancies between selected values and those calculated earlier [ Rathjens G.W., 1953] increase as the temperature increases and amount to 5.4 and 3.1 J/mol*K for S(1500 K) and Cp(1500 K), respectively.
38.19100.
42.28150.
48.84200.
64.23273.15
70.6 ± 1.5298.15
71.05300.
97.67400.
122.03500.
142.64600.
159.92700.
174.52800.
186.99900.
197.671000.
206.851100.
214.761200.
221.591300.
227.501400.
232.621500.

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, 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

C4H7- + Hydrogen cation = Cyclobutane

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Δr1746. ± 8.4kJ/molBranDePuy, Gronert, et al., 1989gas phase; B
Δr1757. ± 8.4kJ/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Quantity Value Units Method Reference Comment
Δr1709. ± 8.8kJ/molH-TSDePuy, Gronert, et al., 1989gas phase; B
Δr1719. ± 8.8kJ/molH-TSPeerboom, Rademaker, et al., 1992gas phase; B

2Ethylene = Cyclobutane

By formula: 2C2H4 = C4H8

Quantity Value Units Method Reference Comment
Δr-86.6 ± 4.2kJ/molEqkQuick, Knecht, et al., 1972gas phase; At 750 K; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, References, Notes

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
LL - Sharon G. Lias and Joel F. Liebman
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 C4H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.8 ± 0.1eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.82 ± 0.05EIHolmes and Lossing, 1991LL
9.6 ± 0.1PEBieri, Burger, et al., 1977LLK
9.92 ± 0.05PERaymonda, 1972LLK
10.06EILossing, 1972LLK
≤10.3PIDoepker and Ausloos, 1966Personal communication from P. Natalis, B. Steiner, and M.G. Inghram; RDSH
10.7 ± 0.1PEBieri, Burger, et al., 1977Vertical value; LLK
10.7 ± 0.1PEBischof, Haselbach, et al., 1970Vertical value; RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H2+16.8?EIHughes and Tiernan, 1969RDSH
C2H3+17.7?EIHughes and Tiernan, 1969RDSH
C2H4+11.0 ± 0.15?EIMeisels, Park, et al., 1970RDSH
C2H5+13.8?EIHughes and Tiernan, 1969RDSH
C3H3+14.8?EIHughes and Tiernan, 1969RDSH
C3H5+11.00CH3EILossing, 1972LLK
C4H6+11.2 ± 0.1H2EIHolmes, Weese, et al., 1977LLK
C4H7+10.91HEILossing, 1972LLK

De-protonation reactions

C4H7- + Hydrogen cation = Cyclobutane

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Δr1746. ± 8.4kJ/molBranDePuy, Gronert, et al., 1989gas phase; B
Δr1757. ± 8.4kJ/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Quantity Value Units Method Reference Comment
Δr1709. ± 8.8kJ/molH-TSDePuy, Gronert, et al., 1989gas phase; B
Δr1719. ± 8.8kJ/molH-TSPeerboom, Rademaker, et al., 1992gas phase; B

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, 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

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

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.
NIST MS number 107

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.


Vibrational and/or electronic energy levels

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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: Takehiko Shimanouchi

Symmetry:   D2d     Symmetry Number σ = 4


 Sym.   No   Approximate   Selected Freq.  Infrared   Raman   Comments 
 Species   type of mode   Value   Rating   Value  Phase  Value  Phase

a1 1 CH2 s-str 2895  D  ia 2916 p liq. FR(2ν2,2ν13)
a1 1 CH2 s-str 2895  D  ia 2866 p liq. FR(2ν2,2ν13)
a1 2 CH2 scis 1443  C  ia 1443 p liq. SF13)
a1 3 Ring str 1001  C  ia 1001 p liq. SF14)
a1 4 CH2 a-str 2975  E  ia CF
a1 5 CH2 rock 741  C  ia 741 dp liq.
a1 6 Ring puck 197  C  ia 197 liq. CF
a2 7 CH2 wag 1260  E  ia  ia CF
a2 8 CH2 twist 1257  E  ia  ia CF
b1 9 CH2 wag 1219  C  ia 1219 dp liq.
b1 10 Ring deform 926  C  ia 926 dp liq.
b1 11 CH2 twist 1222  E  ia CF
b2 12 CH2 s-str 2893  E CF
b2 13 CH2 scis 1443  C 1443 dp liq. SF2)
b2 14 Ring deform 1001  D 1001 p liq. SF3)
b2 15 CH2 a-str 2987  C 2987 S gas
b2 16 CH2 rock 627  C 627 S gas
e 17 CH2 a-str 2952  C 2952 liq.
e 18 CH2 twist 1223  C 1223 W gas
e 19 CH2 rock 749  C 749 W gas
e 20 CH2 s-str 2887  D 2897 S gas
e 20 CH2 s-str 2887  D 2878 S gas
e 21 CH2 scis 1447  C 1447 S gas
e 22 CH2 wag 1257  C 1257 S gas
e 23 Ring deform 898  C 898 S gas

Source: Shimanouchi, 1972

Notes

SStrong
WWeak
iaInactive
pPolarized
dpDepolarized
FRFermi resonance with an overtone or a combination tone indicated in the parentheses.
CFCalculated frequency
SFCalculation shows that the frequency approximately equals that of the vibration indicated in the parentheses.
C3~6 cm-1 uncertainty
D6~15 cm-1 uncertainty
E15~30 cm-1 uncertainty

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Rathjens G.W., 1953
Rathjens G.W., Jr., Infrared absorption spectra, structure and thermodynamic properties of cyclobutane, J. Am. Chem. Soc., 1953, 75, 5634-5642. [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Quick, Knecht, et al., 1972
Quick, L.M.; Knecht, D.A.; Back, M.H., Kinetics of the formation of cyclobutane from ethylene, Int. J. Chem. Kinet., 1972, 4, 61-68. [all data]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [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]

Raymonda, 1972
Raymonda, J.W., Rydberg states in cyclic alkanes, J. Chem. Phys., 1972, 56, 3912. [all data]

Lossing, 1972
Lossing, F.P., Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C3H3, C3H5, and C4H7 radicals and ions, Can. J. Chem., 1972, 50, 3973. [all data]

Doepker and Ausloos, 1966
Doepker, R.D.; Ausloos, P., Gas-phase radiolysis of cyclobutane, J. Chem. Phys., 1966, 44, 1641. [all data]

Bischof, Haselbach, et al., 1970
Bischof, P.; Haselbach, E.; Heilbronner, E., Photoelectron spectrum of cyclobutane, Angew. Chem. Int. Ed. Engl., 1970, 9, 953. [all data]

Hughes and Tiernan, 1969
Hughes, B.M.; Tiernan, T.O., Ionic reactions in gaseous cyclobutane, J. Chem. Phys., 1969, 51, 4373. [all data]

Meisels, Park, et al., 1970
Meisels, G.G.; Park, J.Y.; Giessner, B.G., Ionization and dissociation of C4H8 isomers, J. Am. Chem. Soc., 1970, 92, 254. [all data]

Holmes, Weese, et al., 1977
Holmes, J.L.; Weese, G.M.; Blair, A.S.; Terlouw, J.K., Metastable ion studies IX-Thermochemistry and ion structures among fragmenting [C4H8]+ ions, an electron impact and field ionization investigation, Org. Mass Spectrom., 1977, 12, 424. [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, References