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 Copy

  
• IUPAC Standard InChIKey: VFSFCYAQBIPUSL-UHFFFAOYSA-N Copy
• 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
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• Other names: Cyclopropane, phenyl-; Cyclopropylbenzene; Phenylcyclopropane; 1-Phenylcyclopropane
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Gas Chromatography
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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.

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

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

Reduced pressure boiling point

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

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

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

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

References

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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]

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]

Notes

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• Symbols used in this document:
  

  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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