1-Pentanol

• Formula: C₅H₁₂O
• Molecular weight: 88.1482
• IUPAC Standard InChI: InChI=1S/C5H12O/c1-2-3-4-5-6/h6H,2-5H2,1H3 Copy

  
• IUPAC Standard InChIKey: AMQJEAYHLZJPGS-UHFFFAOYSA-N Copy
• CAS Registry Number: 71-41-0
• 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: Pentyl alcohol; n-Amyl alcohol; n-Butylcarbinol; n-Pentan-1-ol; n-Pentanol; n-Pentyl alcohol; Amyl alcohol; Amylol; Pentanol; 1-Pentyl alcohol; n-C5H11OH; Pentan-1-ol; Pentanol-1; Pentasol; n-Amylalkohol; Alcool amylique; Amyl alcohol, n-; Amyl alcohol, normal; Primary amyl alcohol; UN 1105; 1-Pentol; Primary-N-amyl alcohol; Butyl carbinol; NSC 5707
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
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

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of vaporization

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

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Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C₅H₁₂O⁺ (ion structure unspecified)

Proton affinity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₅H₁₁O^- +  =

By formula: C₅H₁₁O^- + H⁺ = C₅H₁₂O

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

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₅H₁₂O = (C₃H₉Si⁺ • C₅H₁₂O)

Free energy of reaction

(C₅H₁₃O⁺ • ) +  = (C₅H₁₃O⁺ • 2)

By formula: (C₅H₁₃O⁺ • C₅H₁₂O) + C₅H₁₂O = (C₅H₁₃O⁺ • 2C₅H₁₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

(C₅H₁₃O⁺ • 2) +  = (C₅H₁₃O⁺ • 3)

By formula: (C₅H₁₃O⁺ • 2C₅H₁₂O) + C₅H₁₂O = (C₅H₁₃O⁺ • 3C₅H₁₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₅H₁₃O⁺ • 3) +  = (C₅H₁₃O⁺ • 4)

By formula: (C₅H₁₃O⁺ • 3C₅H₁₂O) + C₅H₁₂O = (C₅H₁₃O⁺ • 4C₅H₁₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₅H₁₃O⁺ • 4) +  = (C₅H₁₃O⁺ • 5)

By formula: (C₅H₁₃O⁺ • 4C₅H₁₂O) + C₅H₁₂O = (C₅H₁₃O⁺ • 5C₅H₁₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

References

Go To: Top, Phase change 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.

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Tschamler, Richter, et al., 1949
Tschamler, H.; Richter, E.; Wettig, F., Mixtures of Primry Aliphatic Alcohols with Chlorex and Other Organic Substances. Binary Liquid Mixtures XII., Monatsh. Chem., 1949, 80, 749. [all data]

Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F., Freezing points of orgainic substances VI. New experimental determinations., Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]

Counsell, Lees, et al., 1968
Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XIX. Low-temperature heat capacity and entropy of propan-1-ol, 2-methylpropan-1-ol, and pentan-1-ol, J. Chem. Soc., A, 1968, 1819, https://doi.org/10.1039/j19680001819 . [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal Data on Organic Compounds. XI. The Heat Capacities, Entropies and Free Energies of Ten Compounds Containing Oxygen or Nitrogen, J. Am. Chem. Soc., 1933, 55, 7, 2733, https://doi.org/10.1021/ja01334a016 . [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]

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]

Smith, Anselme, et al., 1986
Smith, R.L.; Anselme, M.J.; Teja, A.S., The Critical Temperatures of Isomeric Pentanols and Heptanols, Fluid Phase Equilib., 1986, 31, 161. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Wormald and James, 2000
Wormald, Christopher J.; James, Gareth F., Specific Enthalpy Increments for Pentan-1-ol at Temperatures up to 623.2 K and 10.1 MPa, J. Chem. Eng. Data, 2000, 45, 2, 348-352, https://doi.org/10.1021/je990275y . [all data]

Aucejo, Burguet, et al., 1994
Aucejo, Antonio; Burguet, M.C.; Monton, Juan B.; Munoz, Rosa; Sanchotello, Margarita; Vazquez, M. Isabel, Isothermal Vapor-Liquid Equilibria of 1-Pentanol with 2-Methyl-1-butanol, 2-Methyl-2-butanol, and 3-Methyl-2-butanol, J. Chem. Eng. Data, 1994, 39, 3, 578-580, https://doi.org/10.1021/je00015a040 . [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]

Ambrose, Sprake, et al., 1972
Ambrose, D.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XXIX. The vapour pressure of diethyl ether, The Journal of Chemical Thermodynamics, 1972, 4, 2, 247-254, https://doi.org/10.1016/0021-9614(72)90063-8 . [all data]

Majer, Svoboda, et al., 1985
Majer, V.; Svoboda, V.; Lencka, M., Enthalpies of vaporization and cohesive energies of dimethylpyridines and trimethylpyridines, The Journal of Chemical Thermodynamics, 1985, 17, 4, 365-370, https://doi.org/10.1016/0021-9614(85)90133-8 . [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]

Counsell, Fenwick, et al., 1970
Counsell, J.F.; Fenwick, J.O.; Lees, E.B., Thermodynamic properties of organic oxygen compounds 24. Vapour heat capacities and enthalpies of vaporization of ethanol, 2-methylpropan-1-ol, and pentan-1-ol, The Journal of Chemical Thermodynamics, 1970, 2, 3, 367-372, https://doi.org/10.1016/0021-9614(70)90007-8 . [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]

Ambrose, Sprake, et al., 1975
Ambrose, D.; Sprake, C.H.S.; Townsend, R., Thermodynamic Properties of Organic Oxygen Compounds. XXXVII. Vapour Pressures of Methanol, Ethanol, Pentan-1-ol, and Octan-1-ol from the Normal Boiling Temperature to the Critical Temperature, J. Chem. Thermodyn., 1975, 7, 2, 185-190, https://doi.org/10.1016/0021-9614(75)90267-0 . [all data]

Ambrose and Sprake, 1970
Ambrose, D.; Sprake, C.H.S., Thermodynamic properties of organic oxygen compounds XXV. Vapour pressures and normal boiling temperatures of aliphatic alcohols, The Journal of Chemical Thermodynamics, 1970, 2, 5, 631-645, https://doi.org/10.1016/0021-9614(70)90038-8 . [all data]

Counsell, Lees, et al., 1968, 2
Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XIX. Low temperature heat capacity and entropy of propan-1-ol, 2-methyl-propan-1-ol, and pentan-1-ol, 1968, J. [all data]

van Miltenburg and van den Berg, 2004
van Miltenburg, J. Cees; van den Berg, Gerrit J.K., Heat Capacities and Derived Thermodynamic Functions of 1-Propanol between 10 K and 350 K and of 1-Pentanol between 85 K and 370 K, J. Chem. Eng. Data, 2004, 49, 3, 735-739, https://doi.org/10.1021/je0499768 . [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]

Parks, Huffman, et al., 1933, 2
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [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]

Peel and Willett, 1975
Peel, J.B.; Willett, G.D., Photoelectron spectroscopic studies of the higher alcohols, Aust. J. Chem., 1975, 28, 2357. [all data]

Harnish, Holmes, et al., 1990
Harnish, D.; Holmes, J.L.; Lossing, F.P.; Mommers, A.A.; Maccoll, A.; Mruzek, M.N., Assigining structures to isomeric [C₅H₁₀]⁺ Ions: the generation of ionized ethylcyclopropane from pentan-1-ol and 1-chloropentane, Org. Mass Spectrom., 1990, 25, 381. [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]

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [all data]

Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M., Intermolecular Forces in Organic Clusters, J. Am. Chem. Soc., 1992, 114, 9, 3312, https://doi.org/10.1021/ja00035a024 . [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Pc	Critical pressure
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  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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