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 | 150.7 ± 1.0 | kJ/mol | Ccb | Fuchs, Hallman, et al., 1982 | Heat of combustion is not reported; ALS |
ΔfH°gas | 150.4 ± 0.8 | kJ/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 | 100.2 ± 0.8 | kJ/mol | Ccb | Kozina, Lukina, et al., 1961 | Error in hf by author |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5076.4 | kJ/mol | Ccb | Fierens and Nasielski, 1962 | Corresponding ΔfHºliquid = 106. kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -5071.0 ± 0.8 | kJ/mol | Ccb | Kozina, Lukina, et al., 1961 | Error in hf by author; Corresponding ΔfHºliquid = 100. kJ/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° | 50.22 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 50.2 ± 0.1 | kJ/mol | V | Fuchs, Hallman, et al., 1982 | Heat of combustion is not reported; ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
446.8 | 1.00 | 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° | 1631. ± 13. | kJ/mol | G+TS | Chou, Dahlke, et al., 1993 | gas phase; Between water, furan |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1599. ± 13. | kJ/mol | IMRB | Chou, Dahlke, et al., 1993 | gas phase; Between water, furan |
ΔrG° | 1607. ± 13. | kJ/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) | 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- + =
By formula: C9H9- + H+ = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1631. ± 13. | kJ/mol | G+TS | Chou, Dahlke, et al., 1993 | gas phase; Between water, furan; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1599. ± 13. | kJ/mol | IMRB | Chou, Dahlke, et al., 1993 | gas phase; Between water, furan; B |
ΔrG° | 1607. ± 13. | kJ/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 |
Mass spectrum (electron ionization)
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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
Spectrum
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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. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-IW- 581 |
NIST MS number | 238986 |
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, Mass spectrum (electron ionization), 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]
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, Mass spectrum (electron ionization), 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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