2-Propanol, 2-methyl-

• Formula: C₄H₁₀O
• Molecular weight: 74.1216
• IUPAC Standard InChI: InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3 Copy

  
• IUPAC Standard InChIKey: DKGAVHZHDRPRBM-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-65-0
• 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.
• Isotopologues:
  • 2-Propanol, 2-methyl-d
  • 2-Propanol, 2-methyl-d
• Other names: tert-Butyl alcohol; tert-Butanol; Ethanol, 1,1-Dimethyl-; Trimethylcarbinol; Trimethylmethanol; 1,1-Dimethylethanol; 2-Methyl-2-propanol; tert-C4H9OH; t-Butanol; tert-Butyl hydroxide; 2-Methylpropanol-2; 2-Methylpropan-2-ol; Alcool butylique tertiaire; Butanol tertiaire; t-Butyl hydroxide; Methanol, trimethyl-; NCI-C55367; 2-Methyl n-propan-2-ol; Methyl-2 propanol-2; Tert.-butyl alcohol
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References, Notes

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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References, Notes

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

Constant pressure heat capacity of solid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References, Notes

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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

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)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References, Notes

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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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

 +  = ( • )

By formula: Cl^- + C₄H₁₀O = (Cl^- • C₄H₁₀O)

C₄H₉O^- +  =

By formula: C₄H₉O^- + H⁺ = C₄H₁₀O

C₄H₉O^- +  = (C₄H₉O^- • )

By formula: C₄H₉O^- + C₄H₁₀O = (C₄H₉O^- • C₄H₁₀O)

 +  = ( • )

By formula: F^- + C₄H₁₀O = (F^- • C₄H₁₀O)

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₄H₁₀O = (C₃H₉Sn⁺ • C₄H₁₀O)

Free energy of reaction

C₅H₁₁O^- +  = (C₅H₁₁O^- • )

By formula: C₅H₁₁O^- + C₄H₁₀O = (C₅H₁₁O^- • C₄H₁₀O)

( • 2) +  = ( • 3)

By formula: (Cl^- • 2C₄H₁₀O) + C₄H₁₀O = (Cl^- • 3C₄H₁₀O)

( • ) +  = ( • 2)

By formula: (Cl^- • C₄H₁₀O) + C₄H₁₀O = (Cl^- • 2C₄H₁₀O)

( • 5) +  = ( • 6)

By formula: (Cl^- • 5C₄H₁₀O) + C₄H₁₀O = (Cl^- • 6C₄H₁₀O)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₁₀O = (CH₆N⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Free energy of reaction

 +  = ( • )

By formula: I^- + C₄H₁₀O = (I^- • C₄H₁₀O)

CN^- +  = (CN^- • )

By formula: CN^- + C₄H₁₀O = (CN^- • C₄H₁₀O)

( • 3) +  = ( • 4)

By formula: (Cl^- • 3C₄H₁₀O) + C₄H₁₀O = (Cl^- • 4C₄H₁₀O)

( • 4) +  = ( • 5)

By formula: (Cl^- • 4C₄H₁₀O) + C₄H₁₀O = (Cl^- • 5C₄H₁₀O)

HS^- +  = (HS^- • )

By formula: HS^- + C₄H₁₀O = (HS^- • C₄H₁₀O)

 +  = ( • )

By formula: NO₂^- + C₄H₁₀O = (NO₂^- • C₄H₁₀O)

 +  = ( • )

By formula: C₅H₅^- + C₄H₁₀O = (C₅H₅^- • C₄H₁₀O)

 +  = ( • )

By formula: Na⁺ + C₄H₁₀O = (Na⁺ • C₄H₁₀O)

Free energy of reaction

 + 2 = C₈H₂₀FO₂^-

By formula: F^- + 2C₄H₁₀O = C₈H₂₀FO₂^-

 +  = C₁₀H₁₅OS^-

By formula: C₆H₅S^- + C₄H₁₀O = C₁₀H₁₅OS^-

 + 2 = C₈H₂₀IO₂^-

By formula: I^- + 2C₄H₁₀O = C₈H₂₀IO₂^-

 + 2 = C₈H₂₀BrO₂^-

By formula: Br^- + 2C₄H₁₀O = C₈H₂₀BrO₂^-

 + 3 = C₁₂H₃₀BrO₃^-

By formula: Br^- + 3C₄H₁₀O = C₁₂H₃₀BrO₃^-

 +  = C₄H₁₀BrO^-

By formula: Br^- + C₄H₁₀O = C₄H₁₀BrO^-

 + 3 = C₁₂H₃₀FO₃^-

By formula: F^- + 3C₄H₁₀O = C₁₂H₃₀FO₃^-

C₆H₅NO₂^- +  = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₁₀O = (C₆H₅NO₂^- • C₄H₁₀O)

 +  = C₄H₉D₁₀FO^-

By formula: F^- + C₄H₁₀O = C₄H₉D₁₀FO^-

 +  =

By formula: C₄H₈ + H₂O = C₄H₁₀O

 +  =

By formula: C₂H₂O + C₄H₁₀O = C₆H₁₂O₂

=  + 

By formula: C₄H₁₀O = C₄H₈ + H₂O

 +  = ( • )

By formula: Li⁺ + C₄H₁₀O = (Li⁺ • C₄H₁₀O)

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, Mass spectrum (electron ionization), References, Notes

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₉O^- +  =

By formula: C₄H₉O^- + H⁺ = C₄H₁₀O

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

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

 +  = C₄H₁₀BrO^-

By formula: Br^- + C₄H₁₀O = C₄H₁₀BrO^-

 + 2 = C₈H₂₀BrO₂^-

By formula: Br^- + 2C₄H₁₀O = C₈H₂₀BrO₂^-

 + 3 = C₁₂H₃₀BrO₃^-

By formula: Br^- + 3C₄H₁₀O = C₁₂H₃₀BrO₃^-

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₁₀O = (CH₆N⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Free energy of reaction

CN^- +  = (CN^- • )

By formula: CN^- + C₄H₁₀O = (CN^- • C₄H₁₀O)

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₄H₁₀O = (C₃H₉Sn⁺ • C₄H₁₀O)

Free energy of reaction

C₄H₉O^- +  = (C₄H₉O^- • )

By formula: C₄H₉O^- + C₄H₁₀O = (C₄H₉O^- • C₄H₁₀O)

 +  = ( • )

By formula: C₅H₅^- + C₄H₁₀O = (C₅H₅^- • C₄H₁₀O)

C₅H₁₁O^- +  = (C₅H₁₁O^- • )

By formula: C₅H₁₁O^- + C₄H₁₀O = (C₅H₁₁O^- • C₄H₁₀O)

C₆H₅NO₂^- +  = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₁₀O = (C₆H₅NO₂^- • C₄H₁₀O)

 +  = C₁₀H₁₅OS^-

By formula: C₆H₅S^- + C₄H₁₀O = C₁₀H₁₅OS^-

 +  = ( • )

By formula: Cl^- + C₄H₁₀O = (Cl^- • C₄H₁₀O)

( • ) +  = ( • 2)

By formula: (Cl^- • C₄H₁₀O) + C₄H₁₀O = (Cl^- • 2C₄H₁₀O)

( • 2) +  = ( • 3)

By formula: (Cl^- • 2C₄H₁₀O) + C₄H₁₀O = (Cl^- • 3C₄H₁₀O)

( • 3) +  = ( • 4)

By formula: (Cl^- • 3C₄H₁₀O) + C₄H₁₀O = (Cl^- • 4C₄H₁₀O)

( • 4) +  = ( • 5)

By formula: (Cl^- • 4C₄H₁₀O) + C₄H₁₀O = (Cl^- • 5C₄H₁₀O)

( • 5) +  = ( • 6)

By formula: (Cl^- • 5C₄H₁₀O) + C₄H₁₀O = (Cl^- • 6C₄H₁₀O)

 +  = C₄H₉D₁₀FO^-

By formula: F^- + C₄H₁₀O = C₄H₉D₁₀FO^-

 +  = ( • )

By formula: F^- + C₄H₁₀O = (F^- • C₄H₁₀O)

 + 2 = C₈H₂₀FO₂^-

By formula: F^- + 2C₄H₁₀O = C₈H₂₀FO₂^-

 + 3 = C₁₂H₃₀FO₃^-

By formula: F^- + 3C₄H₁₀O = C₁₂H₃₀FO₃^-

HS^- +  = (HS^- • )

By formula: HS^- + C₄H₁₀O = (HS^- • C₄H₁₀O)

 +  = ( • )

By formula: I^- + C₄H₁₀O = (I^- • C₄H₁₀O)

 + 2 = C₈H₂₀IO₂^-

By formula: I^- + 2C₄H₁₀O = C₈H₂₀IO₂^-

 +  = ( • )

By formula: Li⁺ + C₄H₁₀O = (Li⁺ • C₄H₁₀O)

 +  = ( • )

By formula: NO₂^- + C₄H₁₀O = (NO₂^- • C₄H₁₀O)

 +  = ( • )

By formula: Na⁺ + C₄H₁₀O = (Na⁺ • C₄H₁₀O)

Free energy of reaction

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes

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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Notes

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

Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S., Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols, J. Org. Chem., 1991, 56, 5108-5110. [all data]

Skinner and Snelson, 1960
Skinner, H.A.; Snelson, A., The heats of combustion of the four isomeric butyl alcohols, Trans. Faraday Soc., 1960, 56, 1776-1783. [all data]

Taft and Riesz, 1955
Taft, R.W., Jr.; Riesz, P., Thermodynamic properties for the system isobutene-t-butyl alcohol, J. Am. Chem. Soc., 1955, 77, 902-904. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Beynon E.T., 1963
Beynon E.T., Jr., The thermodynamic properties of 2-methyl-2-propanol, J. Phys. Chem., 1963, 67, 2761-2765. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Stromsoe E., 1970
Stromsoe E., Heat capacity of alcohol vapors at atmospheric pressure, J. Chem. Eng. Data, 1970, 15, 286-290. [all data]

Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M., Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds, J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]

Parks and Anderson, 1926
Parks, G.S.; Anderson, C.T., Thermal data on organic compounds. III. The heat capacities, entropies and free energies of tertiary butyl alcohol, mannitol, erythritol and normal butyric acid, J. Am. Chem. Soc., 1926, 48, 1506-1512. [all data]

Raley, Rust, et al., 1948
Raley, J.H.; Rust, F.F.; Vaughan, W.E., Decompositions of Di-t-alkyl peroxides. I. Kinetics, J. Am. Chem. Soc., 1948, 70, 88-94. [all data]

Oetting F.L., 1963
Oetting F.L., The heat capacity and entropy of 2-methyl-2-propanol from 15 to 330 K, J. Phys. Chem., 1963, 67, 2757-2761. [all data]

Caceres-Alonso, Costas, et al., 1988
Caceres-Alonso, M.; Costas, M.; Andreoli-Ball, L.; Patterson, D., Steric effects on the self-association of branched and cyclic alcohols in inert solvents. Apparent heat capacities of secondary and tertiary alcohols in hydrocarbons, Can. J. Chem., 1988, 66, 989-998. [all data]

Okano, Ogawa, et al., 1988
Okano, T.; Ogawa, H.; Murakami, S., Molar excess volumes, isentropic compressions, and isobaric heat capacities of methanol-isomeric butanol systems at 298.15 K, Can. J. Chem., 1988, 66, 713-717. [all data]

De Visser, Perron, et al., 1977
De Visser, C.; Perron, G.; Desnoyers, J.E., Volumes and heat capacities of ternary aqueous systems at 25°C. Mixtures of urea, tert-butyl alcohol, N,N-dimethylformamide, and water, J. Amer. Chem. Soc., 1977, 99, 5894-5900. [all data]

De Visser, Perron, et al., 1977, 2
De Visser, C.; Perron, G.; Desnoyers, J.E., The heat capacities, volumes and expansibilities of tert-butyl alcohol - water mixtures form 6 to 65°C, Can. J. Chem., 1977, 55, 856-762. [all data]

Murthy and Subrahmanyam, 1977
Murthy, N.M.; Subrahmanyam, S.V., Behaviour of excess heat capacity of aqueous non-electrolytes, Indian J. Pure Appl. Phys., 1977, 15, 485-489. [all data]

Skold, Suurkuusk, et al., 1976
Skold, R.; Suurkuusk, J.; Wadso, I., Thermochemistry of solutions of biochemical model compounds. 7. Aqueous solutions of some amides, t-butanol, and pentanol, J. Chem. Thermodynam., 1976, 8, 1075-1080. [all data]

Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R., Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases, J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]

Oetting, 1963
Oetting, F.L., The heat capacity and entropy of 2-methyl-2-propanol from 15 to 330!31k, J. Phys. Chem., 1963, 67, 2757-61. [all data]

Parks and Anderson, 1926, 2
Parks, G.S.; Anderson, C.T., Thermal data on organic compounds. III. The heat capacities, entropies and free energies of tertiary butyl alcohol, mannitol, erythritol and normal butyric acid, J. Am. Chem. Soc., 1926, 48, 1506-12. [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]

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]

Ambrose and Townsend, 1963
Ambrose, D.; Townsend, R., Thermodynamic Properties of Organic Oxygen Compounds IX. The Critical Properties and Vapor Pressures Above Five Atmospheres of Six Aliphatic Alcohols, J. Chem. Soc., 1963, 54, 3614-25. [all data]

Krone and Johnson, 1956
Krone, L.H.; Johnson, R.C., Thermodynamic Properties of tert-Butyl ALcohol, AIChE J., 1956, 2, 552-4. [all data]

Pawlewski, 1883
Pawlewski, B., Critical temperatures of some liquids, Ber. Dtsch. Chem. Ges., 1883, 16, 2633-36. [all data]

Ortega, Espiau, et al., 2003
Ortega, Juan; Espiau, Fernando; Postigo, Miguel, Isobaric Vapor-Liquid Equilibria and Excess Quantities for Binary Mixtures of an Ethyl Ester + tert -Butanol and a New Approach to VLE Data Processing, J. Chem. Eng. Data, 2003, 48, 4, 916-924, https://doi.org/10.1021/je0202073 . [all data]

Aucejo, Loras, et al., 1999
Aucejo, Antonio; Loras, Sonia; Muñoz, Rosa; Ordoñez, Luis Miguel, Isobaric vapor--liquid equilibrium for binary mixtures of 2-methylpentane+ethanol and +2-methyl-2-propanol, Fluid Phase Equilibria, 1999, 156, 1-2, 173-183, https://doi.org/10.1016/S0378-3812(99)00029-1 . [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, Counsell, et al., 1970
Ambrose, D.; Counsell, J.F.; Davenport, A.J., The use of Chebyshev polynomials for the representation of vapour pressures between the triple point and the critical point, The Journal of Chemical Thermodynamics, 1970, 2, 2, 283-294, https://doi.org/10.1016/0021-9614(70)90093-5 . [all data]

Beynon and McKetta, 1963
Beynon, Eugene T.; McKetta, John J., THE THERMODYNAMIC PROPERTIES OF 2-METHYL-2-PROPANOL, J. Phys. Chem., 1963, 67, 12, 2761-2765, https://doi.org/10.1021/j100806a060 . [all data]

Majer, Svoboda, et al., 1984
Majer, V.; Svoboda, V.; Hynek, V., On the enthalpy of vaporization of isomeric butanols, J. Chem. Thermodyn., 1984, 16, 1059-1066. [all data]

Sachek, Peshchenko, et al., 1982
Sachek, A.I.; Peshchenko, A.D.; Markovnik, V.S.; Ral'ko, O.V.; Andreevskii, D.N.; Leont'eva, A.A., Termodin. Org. Soedin., 1982, 94. [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]

Brown, Fock, et al., 1969
Brown, I.; Fock, W.; Smith, F., The thermodynamic properties of solutions of normal and branched alcohols in benzene and n-hexane, The Journal of Chemical Thermodynamics, 1969, 1, 3, 273-291, https://doi.org/10.1016/0021-9614(69)90047-0 . [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]

Ambrose and Townsend, 1963, 2
Ambrose, D.; Townsend, R., 681. Thermodynamic properties of organic oxygen compounds. Part IX. The critical properties and vapour pressures, above five atmospheres, of six aliphatic alcohols, J. Chem. Soc., 1963, 3614, https://doi.org/10.1039/jr9630003614 . [all data]

Parks and Barton, 1928
Parks, George S.; Barton, Bernard, VAPOR PRESSURE DATA FOR ISOPROPYL ALCOHOL AND TERTIARY BUTYL ALCOHOL, J. Am. Chem. Soc., 1928, 50, 1, 24-26, https://doi.org/10.1021/ja01388a004 . [all data]

Ambrose and Townsend, 1963, 3
Ambrose, D.; Townsend, R., Thermodynamic Properties of Organic Oxygen Compounds. Part 9. The Critical Properties and Vapour Pressures, above Five Atmospheres, of Six Aliphatic Alcohols, J. Chem. Soc., 1963, 3614-3625, https://doi.org/10.1039/jr9630003614 . [all data]

Biddiscombe, Collerson, et al., 1963
Biddiscombe, D.P.; Collerson, R.R.; Handley, R.; Herington, E.F.G.; Martin, J.F.; Sprake, C.H.S., Thermodynamic Properties of Organic Oxygen Compounds. Part 8. Purification and Vapor Pressures of the Propyl and Butyl Alcohols, J. Chem. Soc., 1963, 1954-1957, https://doi.org/10.1039/jr9630001954 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

Hiraoka and Mizuse, 1987
Hiraoka, K.; Mizuse, S., Gas-Phase Solvation of Cl- with H2O, CH3OH, C2H4OH, i-C3H7OH, n-C3H7OH, and t-C4H9OH, Chem. Phys., 1987, 118, 3, 457, https://doi.org/10.1016/0301-0104(87)85078-4 . [all data]

Sieck, 1985
Sieck, L.W., Thermochemistry of Solvation of NO₂^- and C₆H₅NO₂^- by Polar Molecules in the Vapor Phase. Comparison with Cl^- and Variation with Ligand Structure., J. Phys. Chem., 1985, 89, 25, 5552, https://doi.org/10.1021/j100271a049 . [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Kebarle, 1977
Kebarle, P., Ion Thermochemistry and Solvation from Gas Phase Ion Equilibria, Ann. Rev. Phys. Chem., 1977, 28, 1, 445, https://doi.org/10.1146/annurev.pc.28.100177.002305 . [all data]

Yamdagni and Kebarle, 1971
Yamdagni, R.; Kebarle, P., Hydrogen bonding energies to negative ions from gas phase measurements of ionic equilibria, J. Am. Chem. Soc., 1971, 93, 7139. [all data]

Bogdanov, Peschke, et al., 1999
Bogdanov, B.; Peschke, M.; Tonner, D.S.; Szulejko, J.E.; McMahon, T.B., Stepwise solvation of halides by alcohol molecules in the gas phase, Int. J. Mass Spectrom., 1999, 187, 707-725, https://doi.org/10.1016/S1387-3806(98)14180-5 . [all data]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

Ramond, Davico, et al., 2000
Ramond, T.M.; Davico, G.E.; Schwartz, R.L.; Lineberger, W.C., Vibronic structure of alkoxy radicals via photoelectron spectroscopy, J. Chem. Phys., 2000, 112, 3, 1158-1169, https://doi.org/10.1063/1.480767 . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

DeTuri and Ervin, 1999
DeTuri, V.F.; Ervin, K.M., Competitive threshold collision-induced dissociation: Gas-phase acidities and bond dissociation energies for a series of alcohols, J. Phys. Chem. A, 1999, 103, 35, 6911-6920, https://doi.org/10.1021/jp991459m . [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]

Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E., Anion-alcohol hydrogen bond strengths in the gas phase, J. Am. Chem. Soc., 1984, 106, 4660. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase, J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076 . [all data]

Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W., Relative acidities of water and methanol, and the stabilities of the dimer adducts, J. Phys. Chem., 1986, 90, 6687. [all data]

Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M., Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol, J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014 . [all data]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

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]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Caldwell and Kebarle, 1984
Caldwell, G.; Kebarle, P., Binding energies and structural effects in halide anion-ROH and -RCOOH complexes from gas phase equilibria measurements, J. Am. Chem. Soc., 1984, 106, 967. [all data]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids, J. Am. Chem. Soc., 1987, 109, 6230. [all data]

Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P., Hydration of CN-, NO₂-, NO₃-, and HO- in the gas phase, Can. J. Chem., 1971, 49, 3308. [all data]

Sieck and Meot-ner, 1989
Sieck, L.W.; Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities., J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079 . [all data]

Meot-ner, 1988
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]

Rodgers and Armentrout, 2000
Rodgers, M.T.; Armentrout, P.B., Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation, Mass Spectrom. Rev., 2000, 19, 4, 215, https://doi.org/10.1002/1098-2787(200007)19:4<215::AID-MAS2>3.0.CO;2-X . [all data]

Rodgers and Armentrout, 1999
Rodgers, M.T.; Armentrout, P.B., Absolute Binding Energies of Sodium Ions to Short-Chain Alcohols, CnH2n+2O, n=1-4, Determined by Threshold Collision-Induced Dissociation Experiments and Ab Initio Theory, 1999, 4955. [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Wilkinson, Szulejko, et al., 1992
Wilkinson, F.E.; Szulejko, J.E.; Allison, C.E.; Mcmahon, T.B., Fourier Transform Ion Cyclotron Resonance Investigation of the Deuterium Isotope Effect on Gas Phase Ion/Molecule Hydrogen Bonding Interactions in Alcohol-Fluoride Adduct Ions, Int. J. Mass Spectrom., 1992, 117, 487-505, https://doi.org/10.1016/0168-1176(92)80110-M . [all data]

Eberz and Lucas, 1934
Eberz, W.F.; Lucas, H.J., The hydration of unsaturated compounds. II. The equilibrium between i-butene and t-butanol and the free energy of hydration of i-butene, J. Am. Chem. Soc., 1934, 56, 1230-1234. [all data]

Rice and Greenberg, 1934
Rice, F.O.; Greenberg, J., Ketene. III. Heat of formation and heat of reaction with alcohols, J. Am. Chem. Soc., 1934, 38, 2268-2270. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Shao, Baer, et al., 1988
Shao, J.D.; Baer, T.; Lewis, D.K., Dissociation dynamics of energy-selected ion-dipole complexes. 2. Butyl alcohol ions, J. Phys. Chem., 1988, 92, 5123. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Baker, Betteridge, et al., 1971
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E., Application of photoelectron spectrometry to pesticide analysis. II.Photoelectron spectra of hydroxy-, and halo-alkanes and halohydrins, Anal. Chem., 1971, 43, 375. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [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]

Robin and Kuebler, 1973
Robin, M.B.; Kuebler, N.A., Excited electronic states of the simple alcohols, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 13. [all data]

Lossing, 1977
Lossing, F.P., Heats of formation of some isomeric [C_nH_2n+1]⁺ ions. Substitutional effects on ion stability, J. Am. Chem. Soc., 1977, 99, 7526. [all data]