1-Hexanol

• Formula: C₆H₁₄O
• Molecular weight: 102.1748
• IUPAC Standard InChI: InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3 Copy

  
• IUPAC Standard InChIKey: ZSIAUFGUXNUGDI-UHFFFAOYSA-N Copy
• CAS Registry Number: 111-27-3
• 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:
  • hexanol-d3
  • hexyl-d11 acetate
• Other names: Hexyl alcohol; n-Hexan-1-ol; n-Hexanol; n-Hexyl alcohol; Amylcarbinol; Caproyl alcohol; Hexanol; Pentylcarbinol; 1-Hexyl alcohol; 1-Hydroxyhexane; n-C6H13OH; Hexan-1-ol; Hexanol-(1); Epal 6; NSC 9254
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Gas phase 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-αT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Henry's Law 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 by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

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 compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Proton affinity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₁₃O^- +  =

By formula: C₆H₁₃O^- + H⁺ = C₆H₁₄O

Ion clustering 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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₆H₁₄O = (C₃H₉Sn⁺ • C₆H₁₄O)

Free energy of reaction

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Notes

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

Green J.H.S., 1961
Green J.H.S., Thermodynamic properties of the normal alcohols C1-C12, J. Appl. Chem., 1961, 11, 397-404. [all data]

Chermin H.A.G., 1961
Chermin H.A.G., Thermo data for petrochemicals. Part 28. Gaseous normal alcohols. The important thermo properties are presented for all the gaseous normal alcohols from methanol through n-decanol, Petrol. Refiner, 1961, 40 (4), 127-130. [all data]

Kelley, 1929
Kelley, K.K., The heat capacities of ethyl and hexyl alcohols from 16 to 298 K and the corresponding entropies and free energies, J. Am. Chem. Soc., 1929, 51, 779-87. [all data]

Gude and Teja, 1995
Gude, M.; Teja, A.S., Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols, J. Chem. Eng. Data, 1995, 40, 1025-1036. [all data]

Quadri, Khilar, et al., 1991
Quadri, S.K.; Khilar, K.C.; Kudchadker, A.P.; Patni, M.J., Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable alkanols, J. Chem. Thermodyn., 1991, 23, 67-76. [all data]

Rosenthal and Teja, 1990
Rosenthal, D.J.; Teja, A.S., The Critical Pressures and temperatures of Isomeric Alkanols, Ind. Eng. Chem. to be published 1990 1990, 1990. [all data]

Rosenthal and Teja, 1989
Rosenthal, D.J.; Teja, A.S., Critical pressures and temperatures of isomeric alkanols, Ind. Eng. Chem. Res., 1989, 28, 1693. [all data]

Teja, Lee, et al., 1989
Teja, A.S.; Lee, R.J.; Rosenthal, D.J.; Anselme, M.J., Correlation of the Critical Properties of Alkanes and Alkanols in 5th IUPAC Conference on Alkanes and AlkanolsGradisca, 1989. [all data]

Anselme and Teja, 1988
Anselme, M.J.; Teja, A.S., Critical Temperatures and Densities of Isomeric Alkanols with Six to Ten Carbon Atoms, Fluid Phase Equilib., 1988, 40, 127-34. [all data]

Efremov, 1966
Efremov, Yu.V., Density, Surface Tension, Saturated Vapor Pressurs and Critical Parameters of Alcohols, Zh. Fiz. Khim., 1966, 40, 1240. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Gierycz, Kosowski, et al., 2009
Gierycz, Pawel; Kosowski, Andrzej; Swietlik, Ryszard, Vapor-Liquid Equilibria in Binary Systems Formed by Cyclohexane with Alcohols, J. Chem. Eng. Data, 2009, 54, 11, 2996-3001, https://doi.org/10.1021/je900050z . [all data]

Tan, Li, et al., 2004
Tan, Taijun; Li, Haoran; Wang, Congmin; Jiang, Hui; Han, Shijun, Isothermal and isobaric vapor--liquid equilibria for the binary system trimethylbenzoquinone + n-hexanol, Fluid Phase Equilibria, 2004, 224, 2, 279-283, https://doi.org/10.1016/j.fluid.2004.06.056 . [all data]

Kulikov, Verevkin, et al., 2001
Kulikov, Dmitry; Verevkin, Sergey P.; Heintz, Andreas, Enthalpies of vaporization of a series of aliphatic alcohols, Fluid Phase Equilibria, 2001, 192, 1-2, 187-207, https://doi.org/10.1016/S0378-3812(01)00633-1 . [all data]

Verevkin, 1998
Verevkin, Sergey P., Thermochemistry of phenols: experimental standard molar enthalpies of formation of 2-phenylphenol, 4-phenylphenol, 2,6-diphenylphenol, and 2,2´- and 4,4´-dihydroxybiphenyl, The Journal of Chemical Thermodynamics, 1998, 30, 3, 389-396, https://doi.org/10.1006/jcht.1997.0316 . [all data]

N'Guimbi, Kasehgari, et al., 1992
N'Guimbi, J.; Kasehgari, H.; Mokbel, I.; Jose, J., Tensions de vapeur d'alcools primaires dans le domaine 0,3 Pa à 1,5 kPa, Thermochimica Acta, 1992, 196, 2, 367-377, https://doi.org/10.1016/0040-6031(92)80100-B . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Kemme and Kreps, 1969
Kemme, Herbert R.; Kreps, Saul I., Vapor pressure of primary n-alkyl chlorides and alcohols, J. Chem. Eng. Data, 1969, 14, 1, 98-102, https://doi.org/10.1021/je60040a011 . [all data]

Majer, Svoboda, et al., 1985
Majer, V.; Svoboda, V.; Uchytilová, V.; Finke, M., Enthalpies of vaporization of aliphatic C5 and C6 alcohols, Fluid Phase Equilibria, 1985, 20, 111-118, https://doi.org/10.1016/0378-3812(85)90026-3 . [all data]

Reddy, Rao, et al., 1985
Reddy, K. Dayananda; Rao, M.V. Prabhakara; Ramakrishna, M., Activity coefficients and excess Gibbs free energies for the systems isobutyl methyl ketone(1)-1-pentanol(2) and isobutyl methyl ketone(1)-1-hexanol (2), J. Chem. Eng. Data, 1985, 30, 4, 394-397, https://doi.org/10.1021/je00042a008 . [all data]

Wilhoit and Zwolinski, 1973
Wilhoit, R.C.; Zwolinski, B.J., Physical and thermodynamic properties of aliphatic alcohols, J. Phys. Chem. Ref. Data Suppl., 1973, 1, 2, 1. [all data]

Rose and Supina, 1961
Rose, Arthur; Supina, W.R., Vapor Pressure and Vapor-Liquid Equilibrium Data for Methyl Esters of the Common Saturated Normal Fatty Acids., J. Chem. Eng. Data, 1961, 6, 2, 173-179, https://doi.org/10.1021/je60010a003 . [all data]

Butler, Ramchandani, et al., 1935
Butler, J.A.V.; Ramchandani, C.N.; Thomson, D.W., 58. The solubility of non-electrolytes. Part I. The free energy of hydration of some aliphatic alcohols, J. Chem. Soc., 1935, 280, https://doi.org/10.1039/jr9350000280 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Kelley, 1929, 2
Kelley, K.K., The heat capacities of ethyl and hexyl alcohols from 16°K to 298°K and the corresponding entropies and free energies, J. Am. Chem. Soc., 1929, 51, 779-786. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Buttery, Ling, et al., 1969
Buttery, R.G.; Ling, L.C.; Guadagni, D.G., Volatilities Aldehydes, Ketones, and Esters in Dilute Water Solution, J. Agric. Food Chem., 1969, 17, 385-389. [all data]

Butler, Ramchandani, et al., 1935, 2
Butler, J.A.V.; Ramchandani, C.N.; Thomson, D.W., The Solubility of Non-Electrolytes. Part 1. The Free Energy of Hydration of Some Alphatic Alcohols, J. Chem. Soc., 1935, 280-285, https://doi.org/10.1039/jr9350000280 . [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]

Ashmore and Burgess, 1977
Ashmore, F.S.; Burgess, A.R., Study of Some Medium Size Alcohols and Hydroperoxides by Photoelectron Spectroscopy, J. Chem. Soc. Faraday Trans. 2, 1977, 73, 1247. [all data]

Holmes, Terlouw, et al., 1976
Holmes, J.L.; Terlouw, J.K.; Lossing, F.P., The thermochemistry of C₂H₄O⁺ ions, J. Phys. Chem., 1976, 80, 2860. [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]

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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]

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Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH₃)₃Sn⁺ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Pc	Critical pressure
  S°gas	Entropy of gas at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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