Benzene, cyclopropyl-

Formula: C₉H₁₀
Molecular weight: 118.1757
IUPAC Standard InChI: InChI=1S/C9H10/c1-2-4-8(5-3-1)9-6-7-9/h1-5,9H,6-7H2
IUPAC Standard InChIKey: VFSFCYAQBIPUSL-UHFFFAOYSA-N
CAS Registry Number: 873-49-4
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: Cyclopropane, phenyl-; Cyclopropylbenzene; Phenylcyclopropane; 1-Phenylcyclopropane
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	150.7 ± 1.0	kJ/mol	Ccb	Fuchs, Hallman, et al., 1982	Heat of combustion is not reported; ALS
Δ_fH°_gas	150.4 ± 0.8	kJ/mol	N/A	Kozina, Lukina, et al., 1961	Value computed using Δ_fH_liquid° value of 100.2±0.8 kj/mol from Kozina, Lukina, et al., 1961 and Δ_vapH° value of 50.2±0.1 kj/mol from missing citation.; DRB

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	100.2 ± 0.8	kJ/mol	Ccb	Kozina, Lukina, et al., 1961	Error in hf by author
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-5076.4	kJ/mol	Ccb	Fierens and Nasielski, 1962	Corresponding Δ_fHº_liquid = 106. kJ/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-5071.0 ± 0.8	kJ/mol	Ccb	Kozina, Lukina, et al., 1961	Error in hf by author; Corresponding Δ_fHº_liquid = 100. kJ/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
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
T_boil	444.	K	N/A	Hahn, Corbin, et al., 1968	Uncertainty assigned by TRC = 4. K; TRC
T_boil	438.	K	N/A	Gragson, Greenlee, et al., 1955	Uncertainty assigned by TRC = 3. K; TRC
T_boil	443.65	K	N/A	Lespieau, 1930	Uncertainty assigned by TRC = 2. K; compound identified as "phenyltrimethylene"; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	50.22	kJ/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	50.2 ± 0.1	kJ/mol	V	Fuchs, Hallman, et al., 1982	Heat of combustion is not reported; ALS

Reduced pressure boiling point

T_boil (K)	Pressure (bar)	Reference	Comment
446.8	1.00	Aldrich Chemical Company Inc., 1990	BS
353.2	0.049	Weast and Grasselli, 1989	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

C₉H₉^- + = Benzene, cyclopropyl-

By formula: C₉H₉^- + H⁺ = C₉H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1631. ± 13.	kJ/mol	G+TS	Chou, Dahlke, et al., 1993	gas phase; Between water, furan
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1599. ± 13.	kJ/mol	IMRB	Chou, Dahlke, et al., 1993	gas phase; Between water, furan
Δ_rG°	1607. ± 13.	kJ/mol	IMRB	Andrist, DePuy, et al., 1984	gas phase

Gas phase ion energetics data

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Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₉H₁₀⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	834.9	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	802.4	kJ/mol	N/A	Hunter and Lias, 1998	HL

Proton affinity at 298K

Proton affinity (kJ/mol)	Reference	Comment
832.2	Aue, Guidoni, et al., 2000	Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol)	Reference	Comment
802.5	Aue, Guidoni, et al., 2000	Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.35	PE	Fu and Dunbar, 1978	LLK
8.3 ± 0.1	EI	Koppel, Schwarz, et al., 1974	LLK
8.6	PE	Fu and Dunbar, 1978	Vertical value; LLK
8.61	PE	Shudo, Kobayashi, et al., 1977	Vertical value; LLK
8.66	PE	Prins, Verhoeven, et al., 1977	Vertical value; LLK
8.71	PE	Bruckmann and Klessinger, 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₉H₉⁺	11.4 ± 0.1	H	EI	Koppel, Schwarz, et al., 1974	LLK

De-protonation reactions

C₉H₉^- + = Benzene, cyclopropyl-

By formula: C₉H₉^- + H⁺ = C₉H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1631. ± 13.	kJ/mol	G+TS	Chou, Dahlke, et al., 1993	gas phase; Between water, furan; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1599. ± 13.	kJ/mol	IMRB	Chou, Dahlke, et al., 1993	gas phase; Between water, furan; B
Δ_rG°	1607. ± 13.	kJ/mol	IMRB	Andrist, DePuy, et al., 1984	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

Fuchs, Hallman, et al., 1982
Fuchs, R.; Hallman, J.H.; Perlman, M.O., Thermochemistry of conjugation of simple cyclopropane derivatives, Can. J. Chem., 1982, 60, 1832-1835. [all data]

Kozina, Lukina, et al., 1961
Kozina, M.P.; Lukina, M.Yu.; Zubareya, N.D.; Safonova, I.L.; Skuratov, S.M.; Kazansky, B.A., The energy of combustion of some phenylcyclopropanes, Dokl. Akad. Nauk SSSR, 1961, 138, 843-845. [all data]

Fierens and Nasielski, 1962
Fierens, P.J.C.; Nasielski, J., Chaleurs de combustion de derives cyclopropaniques et pouvoir de conjugaison du groupe cyclopropyle, Bull. Soc. Chim. Belg., 1962, 71, 187-202. [all data]

Hahn, Corbin, et al., 1968
Hahn, R.C.; Corbin, T.F.; Shechter, H., Electrical Effects of Cycloalkyl Groups, J. Am. Chem. Soc., 1968, 90, 3404-15. [all data]

Gragson, Greenlee, et al., 1955
Gragson, J.T.; Greenlee, K.W.; Derfer, J.M.; Boord, C.E., Cyclopropane Hydrocarbons from γ-Bromo Ethers, J. Org. Chem., 1955, 20, 275. [all data]

Lespieau, 1930
Lespieau, R., Phenyltrimethylene, C. R. Hebd. Seances Acad. Sci., 1930, 190, 1129-31. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Chou, Dahlke, et al., 1993
Chou, P.K.; Dahlke, G.D.; Kass, S.R., Unimolecular Rearrangements of Carbanions in the Gas Phase .2. Cyclopropyl Anions, J. Chem. Soc. Chem. Comm., 1993, 115, 1, 315, https://doi.org/10.1021/ja00054a045 . [all data]

Andrist, DePuy, et al., 1984
Andrist, A.H.; DePuy, C.H.; Squires, R.R., Structures of ssomeric anions in the gas phase: Arylallyl and arylcyclopropyl anions, J. Am. Chem. Soc., 1984, 106, 845. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Fu and Dunbar, 1978
Fu, E.W.; Dunbar, R.C., Photodissociation spectroscopy and structural rearrangements in ions of cyclooctatetraene, styrene and related molecules, J. Am. Chem. Soc., 1978, 100, 2283. [all data]

Koppel, Schwarz, et al., 1974
Koppel, C.; Schwarz, H.; Bohlmann, F., Elektronenstossinduzierte fragmentierung von acetylenverbindungen. VIII. Struktur der stabilen und instabilen ionen[C₉H₉]⁺ aus isomeren C₉H₁₀- kohlenwasserstoffen, Org. Mass Spectrom., 1974, 8, 25. [all data]

Shudo, Kobayashi, et al., 1977
Shudo, K.; Kobayashi, T.; Utsunomiya, C., Photoelectron spectral studies on the interaction of three-membered rings with aryl groups, Tetrahedron, 1977, 33, 1721. [all data]

Prins, Verhoeven, et al., 1977
Prins, I.; Verhoeven, J.W.; DeBoer, Th.J.; Worrell, C., Conformational studies on arylcyclopropanes-I, Tetrahedron, 1977, 33, 127. [all data]

Bruckmann and Klessinger, 1974
Bruckmann, P.; Klessinger, M., Photoelektronenspektren organischer verbindungen. V. Wechselwirkung kleiner ringe mit π-systemen, Chem. Ber., 1974, 107, 1108. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
T_boil	Boiling point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas 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 at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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