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:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, 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)

References

Go To: Top, Reaction thermochemistry data, Notes

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

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]

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]

Notes

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:
  

  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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