1-Octanol

Formula: C₈H₁₈O
Molecular weight: 130.2279
IUPAC Standard InChI: InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3
IUPAC Standard InChIKey: KBPLFHHGFOOTCA-UHFFFAOYSA-N
CAS Registry Number: 111-87-5
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: Octyl alcohol; n-Octan-1-ol; n-Octanol; n-Octyl alcohol; Alfol 8; Caprylic alcohol; Heptyl carbinol; Octanol; Octilin; Sipol L8; Alcohol C-8; n-Heptyl carbinol; Octan-1-ol; Prim-n-octyl alcohol; Octanol-(1); Dytol M-83; Lorol 20; Octyl alcohol, normal-primary; Primary octyl alcohol; Epal 8; 1-Hydroxyoctane; Emery 3322; Emery 3324; Lorol C 8-98; 1-Octyl alcohol; NSC 9823
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
Options:
- Switch to calorie-based units

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

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

Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-356. ± 5.	kJ/mol	AVG	N/A	Average of 6 values; Individual data points

Condensed phase thermochemistry data

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

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-426.6 ± 0.6	kJ/mol	Ccb	Mosselman and Dekker, 1975	ALS
Δ_fH°_liquid	-428.0 ± 1.1	kJ/mol	Ccb	Gundry, Harrop, et al., 1969	Heat of formation derived by Cox and Pilcher, 1970; ALS
Δ_fH°_liquid	-425.2 ± 1.1	kJ/mol	Ccb	Chao and Rossini, 1965	see Rossini, 1934; ALS
Δ_fH°_liquid	-435.0 ± 2.7	kJ/mol	Ccb	Green, 1960	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-5294.0 ± 0.6	kJ/mol	Ccb	Mosselman and Dekker, 1975	Corresponding Δ_fHº_liquid = -426.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-5295.5 ± 1.0	kJ/mol	Ccb	Chao and Rossini, 1965	see Rossini, 1934; Corresponding Δ_fHº_liquid = -425.05 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-5285.7 ± 2.7	kJ/mol	Ccb	Green, 1960	Corresponding Δ_fHº_liquid = -434.84 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-5285.6	kJ/mol	Ccb	Verkade and Coops, 1927	Corrected for 298 and 1 atm.; Corresponding Δ_fHº_liquid = -434.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
304.0	298.15	Vesely, Barcal, et al., 1989	T = 298.15 to 318.15 K.; DH
329.5	303.2	Naziev, Bashirov, et al., 1986	T = 303.2 to 448 K. p = 0.1 MPa. Unsmoothed experimental datum given as 2.53 kJ/kg*K.; DH
305.55	298.15	Zegers and Somsen, 1984	DH
318.3	310.67	Griigo'ev, Yanin, et al., 1979	T = 310 to 452 K. p = 0.98 bar.; DH
312.1	298.	Hutchinson and Bailey, 1959	DH
284.5	286.0	Cline and Andrews, 1931	T = 102 to 286 K. Value is unsmoothed experimental datum.; DH
324.3	298.	von Reis, 1881	T = 291 to 470 K.; DH

Reaction thermochemistry data

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

Data compiled as indicated in comments:
B - John E. Bartmess
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

C₈H₁₇O^- + = 1-Octanol

By formula: C₈H₁₇O^- + H⁺ = C₈H₁₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1566. ± 8.8	kJ/mol	G+TS	Higgins and Bartmess, 1998	gas phase; B
Δ_rH°	1563. ± 13.	kJ/mol	CIDC	Haas and Harrison, 1993	gas phase; Kinetic method gives energy-dependent results.; B
Δ_rH°	1556. ± 12.	kJ/mol	G+TS	Boand, Houriet, et al., 1983	gas phase; value altered from reference due to change in acidity scale; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1538. ± 8.4	kJ/mol	IMRE	Higgins and Bartmess, 1998	gas phase; B
Δ_rG°	1535. ± 13.	kJ/mol	H-TS	Haas and Harrison, 1993	gas phase; Kinetic method gives energy-dependent results.; B
Δ_rG°	1528. ± 11.	kJ/mol	CIDC	Boand, Houriet, et al., 1983	gas phase; value altered from reference due to change in acidity scale; B

1-Octanol + = C₈H₁₈O₄S +

By formula: C₈H₁₈O + ClHO₃S = C₈H₁₈O₄S + HCl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	55. ± 1.	kJ/mol	Cm	Markitanova, Barsukov, et al., 1981	liquid phase; solvent: Dichloromethane; Sulfation; ALS

1-Octanol + = C₈H₁₈O₄S

By formula: C₈H₁₈O + O₃S = C₈H₁₈O₄S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	93. ± 2.	kJ/mol	Cm	Markitanova, Barsukov, et al., 1981	liquid phase; solvent: Dichloromethane; ALS

Gas phase ion energetics data

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

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)

Proton affinity at 298K

Proton affinity (kJ/mol)	Reference	Comment
799.	Holmes, Aubry, et al., 1999	MM

De-protonation reactions

C₈H₁₇O^- + = 1-Octanol

By formula: C₈H₁₇O^- + H⁺ = C₈H₁₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1566. ± 8.8	kJ/mol	G+TS	Higgins and Bartmess, 1998	gas phase; B
Δ_rH°	1563. ± 13.	kJ/mol	CIDC	Haas and Harrison, 1993	gas phase; Kinetic method gives energy-dependent results.; B
Δ_rH°	1556. ± 12.	kJ/mol	G+TS	Boand, Houriet, et al., 1983	gas phase; value altered from reference due to change in acidity scale; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1538. ± 8.4	kJ/mol	IMRE	Higgins and Bartmess, 1998	gas phase; B
Δ_rG°	1535. ± 13.	kJ/mol	H-TS	Haas and Harrison, 1993	gas phase; Kinetic method gives energy-dependent results.; B
Δ_rG°	1528. ± 11.	kJ/mol	CIDC	Boand, Houriet, et al., 1983	gas phase; value altered from reference due to change in acidity scale; B

References

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

Mosselman and Dekker, 1975
Mosselman, C.; Dekker, H., Enthalpies of formation of n-alkan-1-ols, J. Chem. Soc. Faraday Trans. 1, 1975, 417-424. [all data]

Gundry, Harrop, et al., 1969
Gundry, H.A.; Harrop, D.; Head, A.J.; Lewis, G.B., Thermodynamic properties of organic oxygen compounds. 21. Enthalpies of combustion of benzoic acid, pentan-1-ol, octan-1-ol, and hexadecan-1-ol, J. Chem. Thermodyn., 1969, 1, 321-332. [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]

Chao and Rossini, 1965
Chao, J.; Rossini, F.D., Heats of combustion, formation, and isomerization of nineteen alkanols, J. Chem. Eng. Data, 1965, 10, 374-379. [all data]

Rossini, 1934
Rossini, F.D., Heats of combustion and of formation of the normal aliphatic alcohols in the gaseous and liquid states, and the energies of their atomic linkages, J. Res. NBS, 1934, 13, 189-197. [all data]

Green, 1960
Green, J.H.S., Revision of the values of the heats of formation of normal alcohols, Chem. Ind. (London), 1960, 1215-1216. [all data]

Verkade and Coops, 1927
Verkade, P.E.; Coops, J., Jr., Calorimetric researches XIV. Heats of combustion of successive members of homologous series: the normal primary aliphatic alcohols, Recl. Trav. Chim. Pays-Bas, 1927, 46, 903-917. [all data]

Vesely, Barcal, et al., 1989
Vesely, F.; Barcal, P.; Zabransky, M.; Svoboda, V., Heat capacities of 4-methyl-2-pentanone, 2,6-dimethyl-4-heptanone, 1-hexanol, 1-heptanol, and 1-octanol in the temperature range 298-318 K, Collect. Czech. Chem. Commun., 1989, 54, 602-607. [all data]

Naziev, Bashirov, et al., 1986
Naziev, Ya.M.; Bashirov, M.M.; Badalov, Yu.A., Experimental study of isobaric specific heat of higher alcohols at high pressures, Inzh.-Fiz. Zhur., 1986, 51, 998-1004. [all data]

Zegers and Somsen, 1984
Zegers, H.C.; Somsen, G., Partial molar volumes and heat capacities in (dimethylformamide + an n-alkanol), J. Chem. Thermodynam., 1984, 16, 225-235. [all data]

Griigo'ev, Yanin, et al., 1979
Griigo'ev, B.A.; Yanin, G.S.; Rastorguev, Yu.L.; Thermophysical parameters of alcohols, Tr. GIAP, 54, 1979, 57-64. [all data]

Hutchinson and Bailey, 1959
Hutchinson, E.; Bailey, L.G., A thermodynamic study of colloidal electrolyte solutions. II. Heat capacities of solubilized systems, experimental, Z. Physik. Chem. [N.G.], 1959, 21, 30-37. [all data]

Cline and Andrews, 1931
Cline, J.K.; Andrews, D.H., Thermal energy studies. III. The octanols, J. Am. Chem. Soc., 1931, 53, 3668-3673. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Higgins and Bartmess, 1998
Higgins, P.R.; Bartmess, J.E., The Gas Phase Acidities of Long Chain Alcohols., Int. J. Mass Spectrom., 1998, 175, 1-2, 71-79, https://doi.org/10.1016/S0168-1176(98)00125-6 . [all data]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [all data]

Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T., The gas phase acidity of aliphatic alcohols, J. Am. Chem. Soc., 1983, 105, 2203. [all data]

Markitanova, Barsukov, et al., 1981
Markitanova, L.I.; Barsukov, I.I.; Passet, B.V., Determination of heat of sulfation by calorimetric titration, J. Gen. Chem. USSR, 1981, 51, 1286-1289. [all data]

Holmes, Aubry, et al., 1999
Holmes, J.L.; Aubry, C.; Mayer, P.M., Proton affinities of primary alkanols: An appraisal of the kinetic method, J. Phys. Chem. A, 1999, 103, 705. [all data]

Notes

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

Symbols used in this document:

C_p,liquid	Constant pressure heat capacity of liquid
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.