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
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering 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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Gas phase thermochemistry data

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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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

References

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

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]

Beauchamp, Caserio, et al., 1974
Beauchamp, J.L.; Caserio, M.C.; McMahon, T.B., Ion-molecule reactions of tert-butyl alcohol by ion cyclotron resonance spectroscopy, J. Am. Chem. Soc., 1974, 96, 6243. [all data]

Potapov and Sorokin, 1972
Potapov, V.K.; Sorokin, V.V., Kinetic energies of products of dissociative photoionization of molecules. I. Aliphatic ketones and alcohols, Khim. Vys. Energ., 1972, 6, 387. [all data]

Potapov and Sorokin, 1970
Potapov, V.K.; Sorokin, V.V., Investigation of ionic molecular reactions proceeding during photoionization of aromatic compounds and alcohols, Dokl. Akad. Nauk SSSR, 1970, 195, 616, In original 848. [all data]

Harrison, Ivko, et al., 1966
Harrison, A.G.; Ivko, A.; Van Raalte, D., Energetics of formation of some oxygenated ions and the proton affinities of carbonyl compounds, Can. J. Chem., 1966, 44, 1625. [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]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  Cp,solid	Constant pressure heat capacity of solid
  IE (evaluated)	Recommended ionization energy
  S°liquid	Entropy of liquid at standard conditions
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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