Cyclobutylcarboxylic acid

Formula: C₅H₈O₂
Molecular weight: 100.1158
IUPAC Standard InChI: InChI=1S/C5H8O2/c6-5(7)4-2-1-3-4/h4H,1-3H2,(H,6,7)
IUPAC Standard InChIKey: TXWOGHSRPAYOML-UHFFFAOYSA-N
CAS Registry Number: 3721-95-7
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.
Other names: Cyclobutanecarboxylic acid
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NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-101.6 ± 0.43	kcal/mol	Ccb	Gutner, Ryadnenko, et al., 1984
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-641.87 ± 0.43	kcal/mol	Ccb	Gutner, Ryadnenko, et al., 1984	Corresponding Δ_fHº_liquid = -101.6 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-641.6	kcal/mol	Ccb	Roth and Ostling, 1913	Corresponding Δ_fHº_liquid = -101.9 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director

Quantity	Value	Units	Method	Reference	Comment
T_boil	468.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
Quantity	Value	Units	Method	Reference	Comment
T_fus	266.05	K	N/A	Pomerantz, Fookson, et al., 1954	Uncertainty assigned by TRC = 1. K; TRC

Reduced pressure boiling point

T_boil (K)	Pressure (atm)	Reference	Comment
359. to 363.	0.020	Frinton Laboratories Inc., 1986	BS

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 compiled by: John E. Bartmess

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

C₅H₇O₂^- + = Cyclobutylcarboxylic acid

By formula: C₅H₇O₂^- + H⁺ = C₅H₈O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	345.8 ± 2.2	kcal/mol	G+TS	Caldwell, Renneboog, et al., 1989	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	338.8 ± 2.0	kcal/mol	IMRE	Caldwell, Renneboog, et al., 1989	gas phase

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

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

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Column type	Active phase	I	Reference	Comment
Packed	SE-30	966.	Peng, Ding, et al., 1988	He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-1	987.	Peng, 2000	15. m/0.53 mm/1. μm, He; Program: 40C(3min) => 8C/min => 200(1min) => 5C/min => 300C(25min)

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1885.	Peng, 2000	15. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1831.	Peng, Yang, et al., 1991	Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes

Gutner, Ryadnenko, et al., 1984
Gutner, N.M.; Ryadnenko, V.L.; Karpenko, N.A.; Makhinya, E.F.; Kiseleva, N.N., Standard enthalpies of formation of some cyclic derivatives, Probl. Kalorim. Khim. Termodin., Dokl. Vses. Konf., 10th, 1984, 1, 196-198. [all data]

Roth and Ostling, 1913
Roth, W.A.; Ostling, G.J., Thermochemische Untersuchungen in der alicyclischen Reihe, Ber., 1913, 46, 309-327. [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]

Pomerantz, Fookson, et al., 1954
Pomerantz, P.; Fookson, A.; Mears, T.W.; Rothberg, S.; Howard, F.L., Synth. and Phys. Prop. of Several Aliphatic and Alicyclic Hydrocarbons hydrocarbons, J. Res. Natl. Bur. Stand. (U. S.), 1954, 52, 59-65. [all data]

Frinton Laboratories Inc., 1986
Frinton Laboratories Inc., Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Peng, 2000
Peng, C.T., Prediction of retention indices. V. Influence of electronic effects and column polarity on retention index, J. Chromatogr. A, 2000, 903, 1-2, 117-143, https://doi.org/10.1016/S0021-9673(00)00901-8 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

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Symbols used in this document:

T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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