Pentane

Formula: C₅H₁₂
Molecular weight: 72.1488
IUPAC Standard InChI: InChI=1S/C5H12/c1-3-5-4-2/h3-5H2,1-2H3
IUPAC Standard InChIKey: OFBQJSOFQDEBGM-UHFFFAOYSA-N
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
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Other names: n-Pentane; Skellysolve A; n-C5H12; Pentan; Pentanen; Pentani; Amyl hydride; NSC 72415
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Reaction thermochemistry data

Go To: Top, References, Notes

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

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Individual Reactions

+ = Pentane

By formula: C₅H₁₀ + H₂ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-30.27 ± 0.58	kcal/mol	Chyd	Molnar, Rachford, et al., 1984	liquid phase; solvent: Dioxane; ALS
Δ_rH°	-29.87 ± 0.42	kcal/mol	Chyd	Molnar, Rachford, et al., 1984	liquid phase; solvent: Hexane; ALS
Δ_rH°	-29.30 ± 0.57	kcal/mol	Chyd	Rogers and Skanupong, 1974	liquid phase; solvent: Hexane; ALS
Δ_rH°	-28.5 ± 0.3	kcal/mol	Chyd	Rogers and McLafferty, 1971	liquid phase; solvent: Hydrocarbon; ALS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	8.91	kcal/mol	N/A	Morse, Parker, et al., 1989	solvent: Pentane; The reaction enthalpy was derived by using the LPHP value for the enthalpy of cleavage of Cr-CO bond in Cr(CO)6, 36.81 kcal/mol Lewis, Golden, et al., 1984, toghether with a PAC value for the reaction Cr(CO)6(solution) + n-C5H12(solution) = Cr(CO)5(n-C5H12)(solution) + CO(solution), 27.89 kcal/mol Morse, Parker, et al., 1989; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	27.9 ± 2.5	kcal/mol	PAC	Morse, Parker, et al., 1989	solvent: Pentane; The reaction enthalpy relies on 0.67 for the quantum yield of CO dissociation; MS

3 + = Pentane

By formula: 3H₂ + C₅H₆ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-96.8 ± 0.1	kcal/mol	Chyd	Roth, Adamczak, et al., 1991	liquid phase; ALS
Δ_rH°	-95.6 ± 1.1	kcal/mol	Chyd	Skinner and Snelson, 1959	liquid phase; solvent: Acetic acid; ALS

3 + = Pentane

By formula: 3H₂ + C₅H₆ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-97.0 ± 0.3	kcal/mol	Chyd	Roth, Adamczak, et al., 1991	liquid phase; ALS
Δ_rH°	-96.0 ± 0.4	kcal/mol	Chyd	Skinner and Snelson, 1959	liquid phase; solvent: Acetic acid; ALS

2 + = Pentane

By formula: 2H₂ + C₅H₈ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-60.22 ± 0.15	kcal/mol	Chyd	Kistiakowsky, Ruhoff, et al., 1936	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -60.79 ± 0.15 kcal/mol; At 355 °K; ALS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-48.4 ± 1.0	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-73.21 ± 0.53	kcal/mol	RSC	Holm, 1981	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-47.7 ± 1.0	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-31.19 ± 0.60	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

2 + = Pentane

By formula: 2H₂ + C₅H₈ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-65.5 ± 0.2	kcal/mol	Chyd	Roth, Kirmse, et al., 1982	liquid phase; solvent: Isooctane; ALS

C₅O₅W (g) + Pentane (g) = C₁₀H₁₂O₅W (g)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-10.6 ± 3.0	kcal/mol	EqG	Brown, Ishikawa, et al., 1990	Temperature range: ca. 300-350 K; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-3.6 ± 1.0	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-48.59	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-28.39	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-65.39	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-55.90	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-47.71	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-52.51	kcal/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

2 + = Pentane

By formula: 2H₂ + C₅H₈ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-54.11 ± 0.15	kcal/mol	Chyd	Dolliver, Gresham, et al., 1937	gas phase; At 355 °K; ALS

Pentane =

By formula: C₅H₁₂ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-1.861	kcal/mol	Eqk	Pines, Kvetinskas, et al., 1945	gas phase; Heat of isomerization; ALS

+ = Pentane

By formula: H₂ + C₅H₁₀ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-28.1 ± 0.2	kcal/mol	Chyd	Egger and Benson, 1966	gas phase; ALS

+ = Pentane

By formula: H₂ + C₅H₁₀ = C₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-27.2 ± 0.2	kcal/mol	Chyd	Egger and Benson, 1966	gas phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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]

Notes

Go To: Top, Reaction thermochemistry data, References

Symbols used in this document:

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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