Methylcyclopropane

Formula: C₄H₈
Molecular weight: 56.1063
IUPAC Standard InChI: InChI=1S/C4H8/c1-4-2-3-4/h4H,2-3H2,1H3
IUPAC Standard InChIKey: VNXBKJFUJUWOCW-UHFFFAOYSA-N
CAS Registry Number: 594-11-6
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.
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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
8.119	50.	Thermodynamics Research Center, 1997	p=1 bar. Selected values are in good agreement with those from other statistical thermodynamics calculation [ Kabo G.Y., 1973].
9.716	100.
11.61	150.
13.83	200.
18.05	273.15
19.65	298.15
19.77	300.
26.061	400.
31.503	500.
35.978	600.
39.694	700.
42.842	800.
45.543	900.
47.880	1000.
49.904	1100.
51.666	1200.
53.196	1300.
54.529	1400.
55.693	1500.
58.01	1750.
59.70	2000.
60.95	2250.
61.90	2500.
62.64	2750.
63.19	3000.

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	0.41 ± 0.16	kcal/mol	Ccb	Good, 1971
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-649.87 ± 0.14	kcal/mol	Ccb	Good, 1971	Corresponding Δ_fHº_liquid = 0.41 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_boil	273.85	K	N/A	Gragson, Greenlee, et al., 1953	Uncertainty assigned by TRC = 0.3 K; TRC
T_boil	273.85	K	N/A	Gragson, Greenlee, et al., 1953	Uncertainty assigned by TRC = 0.3 K; TRC
T_boil	273.88	K	N/A	Anonymous, 1952	Uncertainty assigned by TRC = 0.2 K; TRC
T_boil	277.65	K	N/A	Lagerlof, 1918	Uncertainty assigned by TRC = 3. K; TRC
T_boil	277.65	K	N/A	Demjanoff, 1895	Uncertainty assigned by TRC = 3. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	96.0 ± 0.3	K	AVG	N/A	Average of 8 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_triple	95.640	K	N/A	Pomerantz, Fookson, et al., 1954	Uncertainty assigned by TRC = 0.2 K; TRC

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
5.93	263.	A	Stephenson and Malanowski, 1987	Based on data from 177. to 278. K. See also Stull, 1947.; AC

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
177. to 277.7	3.78280	881.456	-44.806	Stull, 1947	Coefficents calculated by NIST from author's data.

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

C₄H₇^- + = Methylcyclopropane

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	409.2 ± 2.0	kcal/mol	Bran	DePuy, Gronert, et al., 1989	gas phase
Δ_rH°	413.0 ± 3.5	kcal/mol	CIDT	Graul and Squires, 1990	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	401.5 ± 2.1	kcal/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase

C₄H₇^- + = Methylcyclopropane

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	410.5 ± 2.0	kcal/mol	Bran	DePuy, Gronert, et al., 1989	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	402.1 ± 2.1	kcal/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase

C₄H₇^- + = Methylcyclopropane

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	411.0 ± 5.0	kcal/mol	CIDT	Graul and Squires, 1990	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	403.2 ± 5.1	kcal/mol	H-TS	Graul and Squires, 1990	gas phase

Gas phase ion energetics data

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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)

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.30 ± 0.05	EI	Holmes and Lossing, 1991	LL
9.46	EI	Lossing, 1972	LLK
9.9 ± 0.2	EI	Meisels and Giessner, 1971	LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₂H₄⁺	12.5 ± 0.2	?	EI	Meisels, Park, et al., 1970	RDSH
C₃H₅⁺	11.02	CH₃	EI	Lossing, 1972	LLK
C₃H₅⁺	10.9	CH₃	EI	Meisels and Giessner, 1971	LLK
C₄H₇⁺	11.02	H	EI	Lossing, 1972	LLK

De-protonation reactions

C₄H₇^- + = Methylcyclopropane

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	409.2 ± 2.0	kcal/mol	Bran	DePuy, Gronert, et al., 1989	gas phase; B
Δ_rH°	413.0 ± 3.5	kcal/mol	CIDT	Graul and Squires, 1990	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	401.5 ± 2.1	kcal/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase; B

C₄H₇^- + = Methylcyclopropane

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	410.5 ± 2.0	kcal/mol	Bran	DePuy, Gronert, et al., 1989	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	402.1 ± 2.1	kcal/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase; B

C₄H₇^- + = Methylcyclopropane

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	411.0 ± 5.0	kcal/mol	CIDT	Graul and Squires, 1990	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	403.2 ± 5.1	kcal/mol	H-TS	Graul and Squires, 1990	gas phase; B

References

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

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Kabo G.Y., 1973
Kabo G.Y., Thermodynamic properties of some hydrocarbons containing three-membered rings, Vestn. Beloruss. Univ., Ser. 2, 1973, 3-6. [all data]

Good, 1971
Good, W.D., The enthalpies of combustion and formation of some alkyl cyclopropanes, J. Chem. Thermodyn., 1971, 3, 539-546. [all data]

Gragson, Greenlee, et al., 1953
Gragson, J.T.; Greenlee, K.W.; Derfer, J.M.; Boord, C.E., J. Am. Chem. Soc., 1953, 75, 3344-7. [all data]

Anonymous, 1952
Anonymous, R., , Physical Properties of Chemical Substances, Dow Chemical Co., 1952. [all data]

Lagerlof, 1918
Lagerlof, D., Thermodynamic research: reduced formulas for simplified calculations of latent molar heat of evaporation, J. Prakt. Chem., 1918, 98, 136. [all data]

Demjanoff, 1895
Demjanoff, N., Methyltrimethylene, Ber. Dtsch. Chem. Ges., 1895, 28, 21. [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]

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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [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]

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]

Meisels and Giessner, 1971
Meisels, G.G.; Giessner, B.G., Threshold behavior and the determination of appearance potentials from second differential ionization efficiencies, Int. J. Mass Spectrom. Ion Phys., 1971, 7, 489. [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]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
T_boil	Boiling point
T_fus	Fusion (melting) point
T_triple	Triple point temperature
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
Δ_vapH	Enthalpy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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