Benzene, (1-methylethyl)-

• Formula: C₉H₁₂
• Molecular weight: 120.1916
• IUPAC Standard InChI: InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 Copy

  
• IUPAC Standard InChIKey: RWGFKTVRMDUZSP-UHFFFAOYSA-N Copy
• CAS Registry Number: 98-82-8
• 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: Cumene; Cumol; Isopropylbenzene; 2-Phenylpropane; (1-Methylethyl)benzene; Isopropylbenzol; Benzene, isopropyl-; Cumeen; Isopropilbenzene; Isopropylbenzeen; Propane, 2-phenyl-; 2-Fenilpropano; 2-Fenyl-propaan; Rcra waste number U055; UN 1918; (Methylethyl)benzene; Benzene, i-propyl-; i-Propylbenzene; NSC 8776; iso-propylbenzene (cumene); (1-methylethyl)benzene (cumene)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C₉H₁₁^- +  =

By formula: C₉H₁₁^- + H⁺ = C₉H₁₂

 +  = ( • )

By formula: NO^- + C₉H₁₂ = (NO^- • C₉H₁₂)

 +  = ( • )

By formula: Cl^- + C₉H₁₂ = (Cl^- • C₉H₁₂)

Free energy of reaction

 +  =

By formula: H₂ + C₉H₁₀ = C₉H₁₂

 +  =  + 

By formula: C₉H₁₁Cl + C₆H₆ = C₆H₅Cl + C₉H₁₂

 +  =  + 

By formula: C₁₀H₁₄ + C₆H₆ = C₇H₈ + C₉H₁₂

2 =  + 

By formula: 2C₉H₁₂ = C₁₂H₁₈ + C₆H₆

2 =  + 

By formula: 2C₉H₁₂ = C₆H₆ + C₁₂H₁₈

3 +  =

By formula: 3H₂ + C₉H₁₂ = C₉H₁₈

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₉H₁₂⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₉H₁₁^- +  =

By formula: C₉H₁₁^- + H⁺ = C₉H₁₂

Ion clustering data

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, UV/Visible spectrum, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Cl^- + C₉H₁₂ = (Cl^- • C₉H₁₂)

Free energy of reaction

 +  = ( • )

By formula: NO^- + C₉H₁₂ = (NO^- • C₉H₁₂)

UV/Visible spectrum

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Abboud, Jimenez, et al., 1995
Abboud, J.-L.M.; Jimenez, P.; Roux, M.V.; Turrion, C.; Lopez-Mardomingo, C.; Podosenin, A.; Rogers, D.W.; Liebman, J.F., Interrelations of the energetics of amides and alkenes: enthalpies of formation of N,N-dimethyl dertivatives of pivalamide, 1-adamantylcarboxamide and benzamide, and of styrene and its a-, trans-β- and β,β-methylated derivates, J. Phys. Org. Chem., 1995, 8, 15-25. [all data]

Nesterova, Rozhnov, et al., 1985
Nesterova, T.N.; Rozhnov, A.M.; Malova, T.N.; Kovzel, E.N., Molar enthalpies of formation of isopropylchlorobenzenes derived from equilibrium measurements, J. Chem. Thermodyn., 1985, 17, 649-656. [all data]

Tsvetkov, Rozhnov, et al., 1985
Tsvetkov, V.F.; Rozhnov, A.M.; Nesterova, T.N., Study of the equilibrium of isomerization and transalkylation of isopropyltoluenes, Neftekhimiya, 1985, 53-57. [all data]

Popov, Rozhnov, et al., 1974
Popov, V.E.; Rozhnov, A.M.; Satronov, V.S.; Volkova, A.G., Disproportionation equilibrium for isopropylbenzene, Neftekhimiya, 1974, 14, 364-367. [all data]

Miki, 1975
Miki, Y., The thermodynamic properties of C₉H₁₈ naphthenes. I. The determination of the equilibrium constants of the hydrogenation of propyl- and isopropylbenzene and ethyltoluenes, Bull. Chem. Soc. Jpn., 1975, 48, 201-208. [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]

McLoughlin, Morrison, et al., 1979
McLoughlin, R.G.; Morrison, J.D.; Traeger, J.C., Photoionization of the C-1 - C-4 monosubstituted alkyl benzenes: Thermochemistry of [C₇H₇]⁺ and [C₈H₉]⁺ formation, Org. Mass Spectrom., 1979, 14, 104. [all data]

Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J., eIonization energies of organic compounds by equilibrium measurements, J. Am. Chem. Soc., 1978, 100, 6027. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Hammond, Price, et al., 1950
Hammond, V.J.; Price, W.C.; Teegan, J.P.; Walsh, A.D., The absorption spectra of some substituted benzenes and naphthalenes in the vacuum ultra-violet, Faraday Discuss. Chem. Soc., 1950, 9, 53. [all data]

Howell, Goncalves, et al., 1984
Howell, J.O.; Goncalves, J.M.; Amatore, C.; Klasinc, L.; Wightman, R.M.; Kochi, J.K., Electron transfer from aromatic hydrocarbons and their π-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials, J. Am. Chem. Soc., 1984, 106, 3968. [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]

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]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]

Kuskov, et al., 1963
Kuskov, M.M., et al., Ultraviolet Absorption Spectra of Aromatic Hydrocarbons, 1963, 45. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  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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