Benzene, cyclopropyl-
- Formula: C9H10
- Molecular weight: 118.1757
- 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 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
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 36.02 ± 0.24 | kcal/mol | Ccb | Fuchs, Hallman, et al., 1982 | Heat of combustion is not reported; ALS |
ΔfH°gas | 35.9 ± 0.2 | kcal/mol | N/A | Kozina, Lukina, et al., 1961 | Value computed using ΔfHliquid° value of 100.2±0.8 kj/mol from Kozina, Lukina, et al., 1961 and ΔvapH° value of 50.2±0.1 kj/mol from missing citation.; DRB |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 24.0 ± 0.2 | kcal/mol | Ccb | Kozina, Lukina, et al., 1961 | Error in hf by author |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1213.3 | kcal/mol | Ccb | Fierens and Nasielski, 1962 | Corresponding ΔfHºliquid = 25.3 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -1212.0 ± 0.2 | kcal/mol | Ccb | Kozina, Lukina, et al., 1961 | Error in hf by author; Corresponding ΔfHºliquid = 24.0 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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:
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 |
---|---|---|---|---|---|
Tboil | 444. | K | N/A | Hahn, Corbin, et al., 1968 | Uncertainty assigned by TRC = 4. K; TRC |
Tboil | 438. | K | N/A | Gragson, Greenlee, et al., 1955 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 443.65 | K | N/A | Lespieau, 1930 | Uncertainty assigned by TRC = 2. K; compound identified as "phenyltrimethylene"; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.00 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 12.00 ± 0.02 | kcal/mol | V | Fuchs, Hallman, et al., 1982 | Heat of combustion is not reported; ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
446.8 | 0.991 | Aldrich Chemical Company Inc., 1990 | BS |
353.2 | 0.049 | Weast and Grasselli, 1989 | BS |
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 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- + =
By formula: C9H9- + H+ = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 389.8 ± 3.1 | kcal/mol | G+TS | Chou, Dahlke, et al., 1993 | gas phase; Between water, furan |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.1 ± 3.0 | kcal/mol | IMRB | Chou, Dahlke, et al., 1993 | gas phase; Between water, furan |
ΔrG° | 384.0 ± 3.0 | kcal/mol | IMRB | Andrist, DePuy, et al., 1984 | gas phase |
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 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) | 199.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 191.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
198.9 | 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) (kcal/mol) | Reference | Comment |
---|---|---|
191.8 | 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- + =
By formula: C9H9- + H+ = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 389.8 ± 3.1 | kcal/mol | G+TS | Chou, Dahlke, et al., 1993 | gas phase; Between water, furan; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.1 ± 3.0 | kcal/mol | IMRB | Chou, Dahlke, et al., 1993 | gas phase; Between water, furan; B |
ΔrG° | 384.0 ± 3.0 | kcal/mol | IMRB | Andrist, DePuy, et al., 1984 | gas phase; B |
IR 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
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, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | Lardelli and Jeger, 1949 |
---|---|
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. 5467 |
Instrument | n.i.g. |
Melting point | -31 |
Boiling point | 173.6; 80(37) |
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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 1010. | Peng, Hua, et al., 1992 | 30. m/0.32 mm/1.5 μm, 40. C @ 4. min, 8. K/min; Tend: 280. C |
Capillary | Petrocol DH | 1002. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1020. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1375. | Vejaphan, Hsieh, et al., 1988 | 60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min, 175. C @ 20. min |
Capillary | Supelcowax-10 | 1377. | Vejaphan, Hsieh, et al., 1988 | 60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min, 175. C @ 20. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 995. | Zenkevich, 1995 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1414. | Peng, Yang, et al., 1991 | Program: not specified |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 140.4 | Fuentes, Font, et al., 2007 | Column length: 60. m; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Lardelli and Jeger, 1949
Lardelli, G.; Jeger, O.,
Uber die reduktion von α,β-ungesattigten carbonyl-verbindungen nach Wolff-Kishner,
Helv. Chim. Acta, 1949, 32, 1817-1835. [all data]
Peng, Hua, et al., 1992
Peng, C.T.; Hua, R.L.; Maltby, D.,
Prediction of retention indexes. IV. Chain branching in alkylbenzene isomers with C10-13 alkyl chains identified in a scintillator solvent,
J. Chromatogr., 1992, 589, 1-2, 231-239, https://doi.org/10.1016/0021-9673(92)80027-R
. [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]
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]
Vejaphan, Hsieh, et al., 1988
Vejaphan, W.; Hsieh, T.C.Y.; Williams, S.S.,
Volatile flavor components from boiled crayfish (Procambarus clarkii) tail meat,
J. Food Sci., 1988, 53, 6, 1666-1670, https://doi.org/10.1111/j.1365-2621.1988.tb07811.x
. [all data]
Zenkevich, 1995
Zenkevich, I.G.,
Calculation of Gas-Chromatographic Retention Indices from Physico-Chemical Constants of Organic Compounds,
Z. Anal. Chem., 1995, 50, 10, 1048-1056. [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]
Fuentes, Font, et al., 2007
Fuentes, M.J.; Font, R.; Gomez-Rico, M.F.; Martin-Gullon, I.,
Pyrolysis and combustion of waste lubricant oil from diesel cars: Decomposition and pollutants,
J. Anal. Appl. Pyrolysis, 2007, 79, 1-2, 215-226, https://doi.org/10.1016/j.jaap.2006.12.004
. [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, IR Spectrum, UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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