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Benzene, cyclopropyl-

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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
Deltafgas36.02 ± 0.24kcal/molCcbFuchs, Hallman, et al., 1982Heat of combustion is not reported; ALS
Deltafgas35.9 ± 0.2kcal/molN/AKozina, Lukina, et al., 1961Value computed using «DELTA»fHliquid° value of 100.2±0.8 kj/mol from Kozina, Lukina, et al., 1961 and «DELTA»vapH° 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
Deltafliquid24.0 ± 0.2kcal/molCcbKozina, Lukina, et al., 1961Error in hf by author
Quantity Value Units Method Reference Comment
Deltacliquid-1213.3kcal/molCcbFierens and Nasielski, 1962Corresponding «DELTA»fliquid = 25.3 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-1212.0 ± 0.2kcal/molCcbKozina, Lukina, et al., 1961Error in hf by author; Corresponding «DELTA»fliquid = 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
Tboil444.KN/AHahn, Corbin, et al., 1968Uncertainty assigned by TRC = 4. K; TRC
Tboil438.KN/AGragson, Greenlee, et al., 1955Uncertainty assigned by TRC = 3. K; TRC
Tboil443.65KN/ALespieau, 1930Uncertainty assigned by TRC = 2. K; compound identified as "phenyltrimethylene"; TRC
Quantity Value Units Method Reference Comment
Deltavap12.00kcal/molN/AMajer and Svoboda, 1985 
Deltavap12.00 ± 0.02kcal/molVFuchs, Hallman, et al., 1982Heat of combustion is not reported; ALS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
446.80.991Aldrich Chemical Company Inc., 1990BS
353.20.049Weast and Grasselli, 1989BS

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 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- + Hydrogen cation = Benzene, cyclopropyl-

By formula: C9H9- + H+ = C9H10

Quantity Value Units Method Reference Comment
Deltar389.8 ± 3.1kcal/molG+TSChou, Dahlke, et al., 1993gas phase; Between water, furan
Quantity Value Units Method Reference Comment
Deltar382.1 ± 3.0kcal/molIMRBChou, Dahlke, et al., 1993gas phase; Between water, furan
Deltar384.0 ± 3.0kcal/molIMRBAndrist, DePuy, et al., 1984gas 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)199.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity191.8kcal/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
198.9Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
191.8Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.35PEFu and Dunbar, 1978LLK
8.3 ± 0.1EIKoppel, Schwarz, et al., 1974LLK
8.6PEFu and Dunbar, 1978Vertical value; LLK
8.61PEShudo, Kobayashi, et al., 1977Vertical value; LLK
8.66PEPrins, Verhoeven, et al., 1977Vertical value; LLK
8.71PEBruckmann and Klessinger, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C9H9+11.4 ± 0.1HEIKoppel, Schwarz, et al., 1974LLK

De-protonation reactions

C9H9- + Hydrogen cation = Benzene, cyclopropyl-

By formula: C9H9- + H+ = C9H10

Quantity Value Units Method Reference Comment
Deltar389.8 ± 3.1kcal/molG+TSChou, Dahlke, et al., 1993gas phase; Between water, furan; B
Quantity Value Units Method Reference Comment
Deltar382.1 ± 3.0kcal/molIMRBChou, Dahlke, et al., 1993gas phase; Between water, furan; B
Deltar384.0 ± 3.0kcal/molIMRBAndrist, DePuy, et al., 1984gas 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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IR 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

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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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Mass spectrum
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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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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UVVis 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

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Column type Active phase I Reference Comment
CapillaryDB-11010.Peng, Hua, et al., 199230. m/0.32 mm/1.5 «mu»m, 40. C @ 4. min, 8. K/min; Tend: 280. C
CapillaryPetrocol DH1002.White, Hackett, et al., 1992100. m/0.25 mm/0.5 «mu»m, He, 1. K/min; Tstart: 30. C; Tend: 220. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
PackedSE-301020.Peng, Ding, et al., 1988Supelcoport; 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

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Column type Active phase I Reference Comment
CapillarySupelcowax-101375.Vejaphan, Hsieh, et al., 198860. m/0.25 mm/0.25 «mu»m, 40. C @ 5. min, 2. K/min, 175. C @ 20. min
CapillarySupelcowax-101377.Vejaphan, Hsieh, et al., 198860. m/0.25 mm/0.25 «mu»m, 40. C @ 5. min, 2. K/min, 175. C @ 20. min

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone995.Zenkevich, 1995Program: not specified

Normal alkane RI, polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryDB-Wax1414.Peng, Yang, et al., 1991Program: not specified

Lee's RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryDB-5140.4Fuentes, Font, et al., 2007Column 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), 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 «gamma»-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 «pi»-systemen, Chem. Ber., 1974, 107, 1108. [all data]

Lardelli and Jeger, 1949
Lardelli, G.; Jeger, O., Uber die reduktion von «alpha»,«beta»-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, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References