1-Pentanethiol

• Formula: C₅H₁₂S
• Molecular weight: 104.214
• IUPAC Standard InChI: InChI=1S/C5H12S/c1-2-3-4-5-6/h6H,2-5H2,1H3 Copy

  
• IUPAC Standard InChIKey: ZRKMQKLGEQPLNS-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-66-7
• 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: n-Amyl mercaptan; n-Pentyl mercaptan; Amyl hydrosulfide; Amyl mercaptan; Amyl sulfhydrate; Amyl thioalcohol; Pentane-1-thiol; Pentanethiol; Pentyl mercaptan; 1-Mercaptopentane; CH3(CH2)4SH; Mercaptan amylique; Pentalarm; 1-Pentanthiol; 1-Pentylthiol
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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  • Gas Phase Kinetics Database
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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

Condensed 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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(-βT_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

Reaction 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:
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

C₅H₁₁S^- +  =

By formula: C₅H₁₁S^- + H⁺ = C₅H₁₂S

2 +  = 2 + 

By formula: 2C₅H₁₂S + I₂ = 2HI + C₁₀H₂₂S₂

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 by: John E. Bartmess

De-protonation reactions

C₅H₁₁S^- +  =

By formula: C₅H₁₁S^- + H⁺ = C₅H₁₂S

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID; BAIRD (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

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

• gas; HP-GC/MS/IRD

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Kovats' RI, polar column, isothermal

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Kovats' RI, polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

Sunner, 1963
Sunner, S., Corrected heat of combustion and formation values for a number of organic sulphur compounds, Acta Chem. Scand., 1963, 17, 728-730. [all data]

Hubbard, Katz, et al., 1954
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Sunner, 1955
Sunner, S., Thermochemical investigation on organic sulfur compounds IV. On thermochemical sulfur bond energy terms, Acta Chem. Scand., 1955, 9, 837-846. [all data]

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Berthelot, M., Chimie Organique. - Nouvelles recherches sur l'isomerie des ethers sulfocyaniques, Compt. Rend., 1901, 132, 57-58. [all data]

Finke, Scott, et al., 1952
Finke, H.L.; Scott, D.W.; Gross, M.E.; Waddington, G.; Huffman, H.M., The entropy and vapor pressure of 1-pentanethiol, J. Am. Chem. Soc., 1952, 74, 2804-2806. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

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

Cossar, Fournier, et al., 1962
Cossar, B.C.; Fournier, J.O.; Fields, D.L.; Reynolds, D.D., Prepartion of Thiols, J. Org. Chem., 1962, 27, 93. [all data]

Mann and Purdie, 1935
Mann, F.G.; Purdie, D., The Constitution of Complex Metallic Salts III. The Parachors of Palladium and Mercury in Simple and Complex Compounds, J. Chem. Soc., 1935, 1935, 1549. [all data]

Teets, 1934
Teets, D.E., The Relation of the Melting Point to the Number of Carbon Atoms in a Series of Normal Mercaptans, J. Am. Chem. Soc., 1934, 56, 1143. [all data]

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Ellis, L.M.; Reid, E.E., The Preparation and Properties of A Double Series of Aliphatic Mercaptans, J. Am. Chem. Soc., 1932, 54, 1674. [all data]

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Finke, H.L.; McCullough, J.P.; Messerly, J.F.; Guthrie, G.B.; Douslin, D.R., Chemical thermodynamic properties for 1-alkanethiols, J. Chem. Thermodyn., 1970, 2, 27. [all data]

Finke, Scott, et al., 1952, 2
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Reid, 1972
Reid, Robert C., Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00, AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637 . [all data]

Finke, Hossenlopp, et al., 1965
Finke, H.L.; Hossenlopp, I.A.; Berg, W.T., 1-pentanethiol: Heat of vaporization and heat capacity of the vapor, J. Phys. Chem., 1965, 69, 3030. [all data]

Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R., Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [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]

Osborn and Douslin, 1966
Osborn, A.G.; Douslin, D.R., Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum., J. Chem. Eng. Data, 1966, 11, 4, 502-509, https://doi.org/10.1021/je60031a014 . [all data]

Finke, Hossenlopp, et al., 1965, 2
Finke, Herman L.; Hossenlopp, Isham A.; Berg, William T., 1-Pentanethiol: Heat of Vaporization and Heat Capacity of the Vapor ¹, J. Phys. Chem., 1965, 69, 9, 3030-3031, https://doi.org/10.1021/j100893a035 . [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]

Janousek, Reed, et al., 1980
Janousek, B.K.; Reed, K.J.; Brauman, J.I., Electron photodetachment from mercaptyl anions (RS- electron affinities of mercaptyl radicals and the S-H bond strength in mercaptans), J. Am. Chem. Soc., 1980, 102, 3125. [all data]

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Haines, W.E.; Helm, R.V.; Bailey, c.W.; Ball, J.S., Purification and properties of ten organic sulfur compounds, J. Phys. Chem., 1954, 58, 270-278. [all data]

Miller and Bruno, 2003
Miller, K.E.; Bruno, T.J., Isothermal Kováts retention indices of sulfur compounds on a poly(5% diphenyl-95% dimethylsiloxane) stationary phase, J. Chromatogr. A, 2003, 1007, 1-2, 117-125, https://doi.org/10.1016/S0021-9673(03)00958-0 . [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

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Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

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Dutoit, J., Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phases, J. Chromatogr., 1991, 555, 1-2, 191-204, https://doi.org/10.1016/S0021-9673(01)87179-X . [all data]

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Garbuzov, V.G.; Misharina, T.A.; Aerov, A.F.; Golovnya, R.V., Gas chromatographic retention indices for sulphur(II)-containing organic substances, J. Anal. Chem. USSR (Engl. Transl.), 1985, 40, 4, 576-586. [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid 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
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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