Pentane

• Formula: C₅H₁₂
• Molecular weight: 72.1488
• IUPAC Standard InChI: InChI=1S/C5H12/c1-3-5-4-2/h3-5H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: OFBQJSOFQDEBGM-UHFFFAOYSA-N Copy
• CAS Registry Number: 109-66-0
• 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: n-Pentane; Skellysolve A; n-C5H12; Pentan; Pentanen; Pentani; Amyl hydride; NSC 72415
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Fluid Properties
• 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

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

 +  =

By formula: C₅H₁₀ + H₂ = C₅H₁₂

C₁₀H₁₂CrO₅ (solution) =  (solution) + C₅CrO₅ (solution)

By formula: C₁₀H₁₂CrO₅ (solution) = C₅H₁₂ (solution) + C₅CrO₅ (solution)

 (solution) +  (solution) = C₁₀H₁₂CrO₅ (solution) +  (solution)

By formula: C₅H₁₂ (solution) + C₆CrO₆ (solution) = C₁₀H₁₂CrO₅ (solution) + CO (solution)

3 +  =

By formula: 3H₂ + C₅H₆ = C₅H₁₂

3 +  =

By formula: 3H₂ + C₅H₆ = C₅H₁₂

2 +  =

By formula: 2H₂ + C₅H₈ = C₅H₁₂

 (solution) + C₅H₁₁BrMg (solution) = C₆H₅BrMgO (solution) +  (solution)

By formula: C₆H₆O (solution) + C₅H₁₁BrMg (solution) = C₆H₅BrMgO (solution) + C₅H₁₂ (solution)

C₅H₁₁BrMg (solution) +  (g) =  (solution) + Br₂Mg (solution)

By formula: C₅H₁₁BrMg (solution) + HBr (g) = C₅H₁₂ (solution) + Br₂Mg (solution)

 (solution) + C₅H₁₁BrMg (solution) = C₂H₅BrMgO (solution) +  (solution)

By formula: C₂H₆O (solution) + C₅H₁₁BrMg (solution) = C₂H₅BrMgO (solution) + C₅H₁₂ (solution)

C₅H₁₁BrMg (solution) +  (solution) = CH₄BrMgN (solution) +  (solution)

By formula: C₅H₁₁BrMg (solution) + CH₅N (solution) = CH₄BrMgN (solution) + C₅H₁₂ (solution)

2 +  =

By formula: 2H₂ + C₅H₈ = C₅H₁₂

C₅O₅W (g) +  (g) = C₁₀H₁₂O₅W (g)

By formula: C₅O₅W (g) + C₅H₁₂ (g) = C₁₀H₁₂O₅W (g)

C₅H₁₁BrMg (solution) +  (solution) =  (solution) + CH₃BrMg (solution)

By formula: C₅H₁₁BrMg (solution) + CH₄ (solution) = C₅H₁₂ (solution) + CH₃BrMg (solution)

 (solution) + C₅H₁₁BrMg (solution) = C₃HBrMgN₂ (solution) +  (solution)

By formula: C₃H₂N₂ (solution) + C₅H₁₁BrMg (solution) = C₃HBrMgN₂ (solution) + C₅H₁₂ (solution)

 (solution) + C₅H₁₁BrMg (solution) = C₁₂H₁₀BrMgN (solution) +  (solution)

By formula: C₁₂H₁₁N (solution) + C₅H₁₁BrMg (solution) = C₁₂H₁₀BrMgN (solution) + C₅H₁₂ (solution)

C₅H₁₁BrMg (solution) +  (solution) = C₂BrF₃MgO₂ (solution) +  (solution)

By formula: C₅H₁₁BrMg (solution) + C₂HF₃O₂ (solution) = C₂BrF₃MgO₂ (solution) + C₅H₁₂ (solution)

C₅H₁₁BrMg (solution) +  (solution) = C₆BrF₅MgO (cr) +  (solution)

By formula: C₅H₁₁BrMg (solution) + C₆HF₅O (solution) = C₆BrF₅MgO (cr) + C₅H₁₂ (solution)

C₅H₁₁BrMg (solution) +  (solution) = C₂H₂BrF₃MgO (solution) +  (solution)

By formula: C₅H₁₁BrMg (solution) + C₂H₃F₃O (solution) = C₂H₂BrF₃MgO (solution) + C₅H₁₂ (solution)

 (solution) + C₅H₁₁BrMg (solution) = CH₃BrMgO (cr) +  (solution)

By formula: CH₄O (solution) + C₅H₁₁BrMg (solution) = CH₃BrMgO (cr) + C₅H₁₂ (solution)

2 +  =

By formula: 2H₂ + C₅H₈ = C₅H₁₂

=

By formula: C₅H₁₂ = C₅H₁₂

 +  =

By formula: H₂ + C₅H₁₀ = C₅H₁₂

 +  =

By formula: H₂ + C₅H₁₀ = C₅H₁₂

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:
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
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

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

Molnar, Rachford, et al., 1984
Molnar, A.; Rachford, R.; Smith, G.V.; Liu, R., Heats of hydrogenation by a simple and rapid flow calorimetric method, Appl. Catal., 1984, 9, 219-223. [all data]

Rogers and Skanupong, 1974
Rogers, D.W.; Skanupong, S., Heats of hydrogenation of sixteen terminal monoolefins. The alternating effect, J. Phys. Chem., 1974, 78, 2569-2572. [all data]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]

Morse, Parker, et al., 1989
Morse, J.M., Jr.; Parker, G.H.; Burkey, T.J., Organometallics, 1989, 8, 2471. [all data]

Lewis, Golden, et al., 1984
Lewis, K.E.; Golden, D.M.; Smith, G.P., Organometallic bond dissociation energies: Laser pyrolysis of Fe(CO)₅, Cr(CO)₆, Mo(CO)₆, and W(CO)₆, J. Am. Chem. Soc., 1984, 106, 3905. [all data]

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [all data]

Skinner and Snelson, 1959
Skinner, H.A.; Snelson, A., Heats of hydrogenation Part 3., Trans. Faraday Soc., 1959, 55, 405-407. [all data]

Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene, J. Am. Chem. Soc., 1936, 58, 146-153. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Holm, 1983
Holm, T., Acta Chem. Scand. B, 1983, 37, 797. [all data]

Holm, 1981
Holm, T., J. Chem. Soc., Perkin Trans. II, 1981, 464.. [all data]

Roth, Kirmse, et al., 1982
Roth, W.R.; Kirmse, W.; Hoffmann, W.; Lennartz, H.W., Heats of hydrogenation. III. Effect of fluoro substituents on the thermal rearrangement of cyclopropane systems, Chem. Ber., 1982, 115, 2508-2515. [all data]

Brown, Ishikawa, et al., 1990
Brown, C.E.; Ishikawa, Y.; Hackett, P.A.; Rayner, D.M., J. Am. Chem. Soc., 1990, 112, 2530. [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [all data]

Pines, Kvetinskas, et al., 1945
Pines, H.; Kvetinskas, B.; Kassel, L.S.; Ipatieff, V.N., Determination of equilibrium constants for butanes and pentanes, J. Am. Chem. Soc., 1945, 67, 631-637. [all data]

Egger and Benson, 1966
Egger, K.W.; Benson, S.W., Nitric oxide and iodine catalyzed isomerization of olefins. VI. Thermodynamic data from equilibrium studies of the geometrical and positional isomerization of n-pentenes, J. Am. Chem. Soc., 1966, 88, 236-240. [all data]

Traeger, Hudson, et al., 1996
Traeger, J.C.; Hudson, C.E.; McAdoo, D.J., A photoionization study of the ion-neutral complexes [CH₃CH⁺CH₃CH₂CH₃] and [CH₃CH₂CH⁺CH₃CH₃] in the gas phase: Formation, H-transfer and C-C bond formation between partners, and channeling of energy into dissociation, J. Am. Soc. Mass Spectrom., 1996, 7, 73. [all data]

Luo and Pacey, 1992
Luo, Y.-R.; Pacey, P.D., Effects of alkyl substitution on ionization energies of alkanes and haloalkanes and on heats of formation of their molecular cations. Part 2. Alkanes and chloro-, bromo- and iodoalkanes, Int. J. Mass Spectrom. Ion Processes, 1992, 112, 63. [all data]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Lias, 1982
Lias, S.G., Thermochemical information from ion-molecule rate constants, Ion Cyclotron Reson. Spectrom. 1982, 1982, 409. [all data]

Mautner(Meot-Ner), Sieck, et al., 1981
Mautner(Meot-Ner), M.; Sieck, L.W.; Ausloos, P., Ionization of normal alkanes: Enthalpy, entropy, structural, and isotope effects, J. Am. Chem. Soc., 1981, 103, 5342. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Lias, Ausloos, et al., 1976
Lias, S.G.; Ausloos, P.; Horvath, Z., Charge transfer reactions in alkane and cycloalkane systems. Estimated ionization potentials, Int. J. Chem. Kinet., 1976, 8, 725. [all data]

Ikuta, Yoshihara, et al., 1973
Ikuta, S.; Yoshihara, K.; Shiokawa, T.; Jinno, M.; Yokoyama, Y.; Ikeda, S., Photoelectron spectroscopy of cyclohexane, cyclopentane, and some related compounds, Chem. Lett., 1973, 1237. [all data]

Flesch and Svec, 1973
Flesch, G.D.; Svec, H.J., Fragmentation reactions in the mass spectrometer for C₂-C₅ alkanes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 1187. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Steiner, Giese, et al., 1961
Steiner, B.; Giese, C.F.; Inghram, M.G., Photoionization of alkanes. Dissociation of excited molecular ions, J. Chem. Phys., 1961, 34, 189. [all data]

Wolkoff and Holmes, 1978
Wolkoff, P.; Holmes, J.L., Fragmentations of alkane molecular ions, J. Am. Chem. Soc., 1978, 100, 7346. [all data]

Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L., Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Org. Mass Spectrom., 1982, 17, 123. [all data]

Lossing and Semeluk, 1970
Lossing, F.P.; Semeluk, G.P., Free radicals by mass spectrometry. XLII.Ionization potentials and ionic heats of formation for C₁-C₄ alkyl radicals, Can. J. Chem., 1970, 48, 955. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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