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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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-39.94	kcal/mol	N/A	Good and Smith, 1969	Value computed using Δ_fH_liquid° value of -198.7±0.7 kj/mol from Good and Smith, 1969 and Δ_vapH° value of 31.6 kj/mol from Prosen and Rossini, 1945.; DRB
Δ_fH°_gas	-39.96 ± 0.19	kcal/mol	Ccb	Prosen and Rossini, 1945	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	92.93 ± 0.20	cal/mol*K	N/A	Scott D.W., 1974	This reference does not contain the original experimental data. Experimental entropy value is based on the results [ Messerly J.F., 1967] for S(liquid).; GT

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
26.429	200.	Scott D.W., 1974, 2	Recommended values were obtained from the consistent correlation scheme for alkanes [ Scott D.W., 1974, Scott D.W., 1974, 2]. This approach gives a better agreement with experimental data than the statistical thermodynamics calculation [ Pitzer K.S., 1944, Pitzer K.S., 1946] (see also [ Waddington G., 1949]).; GT
31.919	273.15
34.08 ± 0.05	298.15
34.240	300.
43.389	400.
51.931	500.
59.300	600.
65.500	700.
70.801	800.
75.301	900.
79.199	1000.
82.500	1100.
85.399	1200.
88.000	1300.
90.000	1400.
93.000	1500.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
37.349 ± 0.074	333.85	Waddington G., 1947	GT
40.220 ± 0.081	365.15
43.301 ± 0.086	398.85
46.391 ± 0.093	433.70
49.460 ± 0.098	468.90

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, IR Spectrum, References, Notes

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

+ = 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

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

References

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Good and Smith, 1969
Good, W.D.; Smith, N.K., Enthalpies of combustion of toluene, benzene, cyclohexane, cyclohexene, methylcyclopentane, 1-methylcyclopentene, and n-hexane, J. Chem. Eng. Data, 1969, 14, 102-106. [all data]

Prosen and Rossini, 1945
Prosen, E.J.; Rossini, F.D., Heats of combustion and formation of the paraffin hydrocarbons at 25° C, J. Res. NBS, 1945, 263-267. [all data]

Scott D.W., 1974
Scott D.W., Correlation of the chemical thermodynamic properties of alkane hydrocarbons, J. Chem. Phys., 1974, 60, 3144-3165. [all data]

Messerly J.F., 1967
Messerly J.F., Low-temperature thermal data for n-pentane, n-heptadecane, and n-octadecane. Revised thermodynamic functions for the n-alkanes, C5-C18, J. Chem. Eng. Data, 1967, 12, 338-346. [all data]

Scott D.W., 1974, 2
Scott D.W., Chemical Thermodynamic Properties of Hydrocarbons and Related Substances. Properties of the Alkane Hydrocarbons, C1 through C10 in the Ideal Gas State from 0 to 1500 K. U.S. Bureau of Mines, Bulletin 666, 1974. [all data]

Pitzer K.S., 1944
Pitzer K.S., Thermodynamics of gaseous paraffins. Specific heat and related properties, Ind. Eng. Chem., 1944, 36, 829-831. [all data]

Pitzer K.S., 1946
Pitzer K.S., The entropies and related properties of branched paraffin hydrocarbons, Chem. Rev., 1946, 39, 435-447. [all data]

Waddington G., 1949
Waddington G., Experimental vapor heat capacities and heats of vaporization of 2-methylpentane, 3-methylpentane, and 2,3-dimethylbutane, J. Am. Chem. Soc., 1949, 71, 3902-3906. [all data]

Waddington G., 1947
Waddington G., Experimental vapor heat capacities and heats of vaporization of n-hexane and 2,2-dimethylbutane, J. Am. Chem. Soc., 1947, 69, 2275-2279. [all data]

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]

Notes

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
S°_gas	Entropy of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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