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
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes
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 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Gas Chromatography, References, Notes
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 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
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, Gas phase ion energetics data, 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]
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]
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]
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, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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