n-Hexane

Formula: C₆H₁₄
Molecular weight: 86.1754
IUPAC Standard InChI: InChI=1S/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3
IUPAC Standard InChIKey: VLKZOEOYAKHREP-UHFFFAOYSA-N
CAS Registry Number: 110-54-3
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.
Isotopologues:
- Hexane-d14
- Hexane-d7
Other names: Hexane; Skellysolve B; n-C6H14; Esani; Heksan; Hexanen; Hexyl hydride; Gettysolve-B; NCI-C60571; NSC 68472
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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, 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

+ = n-Hexane

By formula: H₂ + C₆H₁₂ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-30.0 ± 0.6	kcal/mol	AVG	N/A	Average of 8 values; Individual data points

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-60.3 ± 0.4	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS
Δ_rH°	-60.69 ± 0.65	kcal/mol	Chyd	Molnar, Rachford, et al., 1984	liquid phase; solvent: Dioxane; ALS
Δ_rH°	-60.17 ± 0.37	kcal/mol	Chyd	Turner, Mallon, et al., 1973	liquid phase; solvent: Glacial acetic acid; ALS
Δ_rH°	-60.03 ± 0.10	kcal/mol	Chyd	Kistiakowsky, Ruhoff, et al., 1936	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -60.53 ± 0.15 kcal/mol; At 355 °K; ALS

+ = n-Hexane

By formula: H₂ + C₆H₁₂ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-27.75 ± 0.11	kcal/mol	Chyd	Rogers, Crooks, et al., 1987	liquid phase; ALS
Δ_rH°	-115.0 ± 0.83	kcal/mol	Chyd	Rogers and Crooks, 1983	liquid phase; solvent: Hexane; ALS
Δ_rH°	-26.59 ± 0.27	kcal/mol	Chyd	Rogers, Papadimetriou, et al., 1975	liquid phase; solvent: Hexane; ALS

+ = n-Hexane

By formula: H₂ + C₆H₁₂ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-29.06 ± 0.076	kcal/mol	Chyd	Rogers, Crooks, et al., 1987	liquid phase; ALS
Δ_rH°	-28.52 ± 0.29	kcal/mol	Chyd	Rogers, Papadimetriou, et al., 1975	liquid phase; solvent: Hexane; ALS
Δ_rH°	-28.57 ± 0.29	kcal/mol	Chyd	Rogers and Siddiqui, 1975	liquid phase; solvent: n-Hexane; ALS

+ = n-Hexane

By formula: C₆H₁₂ + H₂ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-28.18 ± 0.17	kcal/mol	Chyd	Rogers, Crooks, et al., 1987	liquid phase; ALS
Δ_rH°	-28.18 ± 0.20	kcal/mol	Chyd	Rogers and Crooks, 1983	liquid phase; solvent: Hexane; ALS
Δ_rH°	-26.24 ± 0.41	kcal/mol	Chyd	Rogers, Papadimetriou, et al., 1975	liquid phase; solvent: Hexane; ALS

+ = n-Hexane

By formula: H₂ + C₆H₁₂ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-28.56 ± 0.16	kcal/mol	Chyd	Rogers, Crooks, et al., 1987	liquid phase; ALS
Δ_rH°	-28.44 ± 0.19	kcal/mol	Chyd	Rogers and Crooks, 1983	liquid phase; solvent: Hexane; ALS
Δ_rH°	-27.05 ± 0.22	kcal/mol	Chyd	Rogers, Papadimetriou, et al., 1975	liquid phase; solvent: Hexane; ALS

3 + = n-Hexane

By formula: 3H₂ + C₆H₈ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-81.0 ± 0.6	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS
Δ_rH°	-80.50 ± 0.33	kcal/mol	Chyd	Turner, Mallon, et al., 1973	liquid phase; solvent: Glacial acetic acid; ALS

3 + = n-Hexane

By formula: 3H₂ + C₆H₈ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-80.0 ± 0.6	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS
Δ_rH°	-79.43 ± 0.22	kcal/mol	Chyd	Turner, Mallon, et al., 1973	liquid phase; solvent: Glacial acetic acid; ALS

4 + = n-Hexane

By formula: 4H₂ + C₆H₆ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-139.3 ± 1.0	kcal/mol	Chyd	Skinner and Snelson, 1959	liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, Original value = -139.4 ± 1.0 kcal/mol; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-53.9 ± 0.3	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-52.9 ± 0.3	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-52.4 ± 0.4	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-58.4 ± 0.4	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-57.6 ± 0.4	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-51.4 ± 0.4	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-50.5 ± 0.4	kcal/mol	Chyd	Fang and Rogers, 1992	liquid phase; solvent: Cyclohexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-63.0 ± 0.2	kcal/mol	Chyd	Roth, Kirmse, et al., 1982	liquid phase; solvent: Isooctane; ALS

4 + = n-Hexane

By formula: 4H₂ + C₆H₆ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-124.7 ± 0.4	kcal/mol	Chyd	Roth, Hopf, et al., 1994	liquid phase; solvent: Isooctane; ALS

C₅O₅W (g) + n-Hexane (g) = C₁₁H₁₄O₅W (g)

By formula: C₅O₅W (g) + C₆H₁₄ (g) = C₁₁H₁₄O₅W (g)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-10.8 ± 3.0	kcal/mol	EqG	Brown, Ishikawa, et al., 1990	Temperature range: ca. 300-350 K; MS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-69.16 ± 0.11	kcal/mol	Chyd	Rogers, Dagdagan, et al., 1979	liquid phase; solvent: Hexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-65.11 ± 0.28	kcal/mol	Chyd	Rogers, Dagdagan, et al., 1979	liquid phase; solvent: Hexane; ALS

2 + = n-Hexane

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-65.7 ± 0.4	kcal/mol	Chyd	Rogers, Dagdagan, et al., 1979	liquid phase; solvent: Hexane; ALS

n-Hexane =

By formula: C₆H₁₄ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-1.30 ± 0.21	kcal/mol	Ciso	Prosen and Rossini, 1941	liquid phase; Calculated from ΔHc; ALS

n-Hexane =

By formula: C₆H₁₄ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-0.76 ± 0.19	kcal/mol	Ciso	Prosen and Rossini, 1941	liquid phase; Calculated from ΔHc; ALS

n-Hexane =

By formula: C₆H₁₄ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-1.96 ± 0.20	kcal/mol	Ciso	Prosen and Rossini, 1941	liquid phase; Calculated from ΔHc; ALS

n-Hexane =

By formula: C₆H₁₄ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-3.49 ± 0.18	kcal/mol	Ciso	Prosen and Rossini, 1941	liquid phase; Calculated from ΔHc; ALS

5 + = n-Hexane

By formula: 5H₂ + C₆H₄ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-168.5 ± 0.4	kcal/mol	Chyd	Roth, Adamczak, et al., 1991	liquid phase; ALS

5 + = n-Hexane

By formula: 5H₂ + C₆H₄ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-169.4 ± 0.4	kcal/mol	Chyd	Roth, Adamczak, et al., 1991	liquid phase; ALS

3 + C₆H₈ = n-Hexane

By formula: 3H₂ + C₆H₈ = C₆H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-103.2 ± 0.3	kcal/mol	Chyd	Roth, Adamczak, et al., 1991	liquid phase; ALS

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, References, Notes

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

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	10.13 ± 0.10	eV	N/A	N/A	L

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.29	EST	Luo and Pacey, 1992	LL
9.97	EQ	Sieck and Mautner(Meot-Ner), 1982	LBLHLM
10.13 ± 0.10	EVAL	Lias, 1982	LBLHLM
10.03 ± 0.15	EQ	Mautner(Meot-Ner), Sieck, et al., 1981	LLK
10.16	EQ	Lias, Ausloos, et al., 1976	LLK
10.22	PE	Ikuta, Yoshihara, et al., 1973	LLK
10.27	PE	Dewar and Worley, 1969	RDSH
10.18	PI	Watanabe, Nakayama, et al., 1962	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₆⁺	11.00 ± 0.035	C₃H₈	PI	Steiner, Giese, et al., 1961	RDSH
C₃H₇⁺	11.42	C₃H₇	EI	Potzinger and Bunau, 1969	RDSH
C₃H₇⁺	11.33 ± 0.055	C₃H₇	PI	Steiner, Giese, et al., 1961	RDSH
C₄H₈⁺	11.00 ± 0.015	C₂H₆	PI	Steiner, Giese, et al., 1961	RDSH
C₄H₉⁺	11.05	C₂H₅	EI	Potzinger and Bunau, 1969	RDSH
C₄H₉⁺	11.03 ± 0.07	C₂H₅	PI	Steiner, Giese, et al., 1961	RDSH
C₅H₁₀⁺	11.005 ± 0.055	CH₄	PI	Steiner, Giese, et al., 1961	RDSH
C₅H₁₁⁺	11.045 ± 0.085	CH₃	PI	Steiner, Giese, et al., 1961	RDSH

References

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

Fang and Rogers, 1992
Fang, W.; Rogers, D.W., Enthalpy of hydrogenation of the hexadienes and cis- and trans-1,3,5-hexatriene, J. Org. Chem., 1992, 57, 2294-2297. [all data]

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]

Turner, Mallon, et al., 1973
Turner, R.B.; Mallon, B.J.; Tichy, M.; Doering, W.v.E.; Roth, W.R.; Schroder, G., Heats of hydrogenation. X. Conjugative interaction in cyclic dienes and trienes, J. Am. Chem. Soc., 1973, 95, 8605-8610. [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]

Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K., Enthalpies of hydrogenation of the hexenes, J. Chem. Thermodyn., 1987, 19, 1209-1215. [all data]

Rogers and Crooks, 1983
Rogers, D.W.; Crooks, E.L., Enthalpies of hydrogenation of the isomers of n-hexene, J. Chem. Thermodyn., 1983, 15, 1087-1092. [all data]

Rogers, Papadimetriou, et al., 1975
Rogers, D.W.; Papadimetriou, P.M.; Siddiqui, N.A., An improved hydrogen microcalorimeter for use with large molecules, Mikrochim. Acta, 1975, 2, 389-400. [all data]

Rogers and Siddiqui, 1975
Rogers, D.W.; Siddiqui, N.A., Heats of hydrogenation of large molecules. I. Esters of unsaturated fatty acids, J. Phys. Chem., 1975, 79, 574-577. [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]

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]

Roth, Hopf, et al., 1994
Roth, W.R.; Hopf, H.; Horn, C., Propargyl-Stabilisierungsenergie, Chem. Ber., 1994, 127, 1781-1795. [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]

Rogers, Dagdagan, et al., 1979
Rogers, D.W.; Dagdagan, O.A.; Allinger, N.L., Heats of hydrogenation and formation of linear alkynes and a molecular mechanics interpretation, J. Am. Chem. Soc., 1979, 101, 671-676. [all data]

Prosen and Rossini, 1941
Prosen, E.J.R.; Rossini, F.D., Heats of isomerization of the five hexanes, J. Res. NBS, 1941, 27, 289-310. [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]

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]

Sieck and Mautner(Meot-Ner), 1982
Sieck, L.W.; Mautner(Meot-Ner), M., Ionization energies and entropies of cycloalkanes. Kinetics of free energy controlled charge-transfer reactions, J. Phys. Chem., 1982, 86, 3646. [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]

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]

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]

Potzinger and Bunau, 1969
Potzinger, P.; Bunau, G.v., Empirische Beruksichtigung von Uberschussenergien bei der Auftrittspotentialbestimmung, Ber. Bunsen-Ges. Phys. Chem., 1969, 73, 466. [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

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
IE (evaluated)	Recommended ionization energy
Δ_rH°	Enthalpy of reaction at standard conditions