2-Butanol

• Formula: C₄H₁₀O
• Molecular weight: 74.1216
• IUPAC Standard InChI: InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: BTANRVKWQNVYAZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 78-92-2
• 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.
• Species with the same structure:
  • 2-Butanol
• Stereoisomers:
  • 2-Butanol, (R)-
  • (S)-butan-2-ol
• Other names: sec-Butyl Alcohol; sec-Butanol; CCS 301; Ethyl methyl carbinol; Methyl ethyl carbinol; 1-Methyl-1-propanol; 1-Methylpropyl alcohol; 2-Hydroxybutane; sec-C4H9OH; Butane, 2-hydroxy-; Butanol-2; Butan-2-ol; 2-Butyl alcohol; s-Butyl alcohol; Butylene hydrate; DL-sec-Butanol; DL-2-Butanol; Alcool butylique secondaire; Butanol secondaire; s-Butanol; 1-Methyl propanol; n-Butan-2-ol; NSC 25499
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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
RCD - Robert C. Dunbar

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

C₄H₉O^- +  =

By formula: C₄H₉O^- + H⁺ = C₄H₁₀O

 +  =

By formula: H₂ + C₄H₈O = C₄H₁₀O

=  + 

By formula: C₄H₁₀O = H₂ + C₄H₈O

 +  =

By formula: C₄H₈ + C₄H₁₀O = C₈H₁₈O

 +  =

By formula: C₂H₂O + C₄H₁₀O = C₆H₁₂O₂

 +  = ( • )

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

 +  = ( • )

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

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 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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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

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

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics 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.

Chao and Rossini, 1965
Chao, J.; Rossini, F.D., Heats of combustion, formation, and isomerization of nineteen alkanols, J. Chem. Eng. Data, 1965, 10, 374-379. [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]

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]

Andon R.J.L., 1971
Andon R.J.L., Thermodynamic properties of organic oxygen compounds. Part XXVII. (+/-)-Butan-2-ol and (+)-butan-2-ol, J. Chem. Soc. A, 1971, 661-664. [all data]

Buckley E., 1965
Buckley E., Equilibria in some secondary alcohol + hydrogen + ketone systems, Trans. Faraday Soc., 1965, 61, 1618-1625. [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]

Rodionov P.P., 1969
Rodionov P.P., Thermodynamic functions of 2-butanol (d,l), Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol., 1969, 12, 1214-1218. [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]

Berman N.S., 1962
Berman N.S., Thermodynamic properties of 2-butanol, J. Phys. Chem., 1962, 66, 1444-1448. [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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [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]

Buckley and Herington, 1965
Buckley, E.; Herington, E.F.G., Equilibria in some secondary alcohol + hydrogen + ketone systems, Trans. Faraday Soc., 1965, 61, 1618-1625. [all data]

Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B., Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol, J. Am. Chem. Soc., 1946, 68, 1149-1151. [all data]

Kolb and Burwell, 1945
Kolb, H.J.; Burwell, R.L., Jr., Equilibrium in the dehydrogenation of secondary propyl and butyl alcohols, J. Am. Chem. Soc., 1945, 67, 1084-1088. [all data]

Sharonov, Mishentseva, et al., 1991
Sharonov, K.G.; Mishentseva, Y.B.; Rozhnov, A.M.; Miroshnichenko, E.A.; Korchatova, L.I., Molar enthalpies of formation and vaporizqation of t-butoxybutanes and thermodynamics of their synthesis from a butanol and 2-methylpropene I. Equilibria of synthesis reactions of t-butoxybutanes in the liquid phase, J. Chem. Thermodyn., 1991, 23, 141-145. [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]

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]

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]

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]

Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A., Low energy, low temperature mass spectra, Org. Mass Spectrom., 1984, 19, 379. [all data]

Holmes, Burgers, et al., 1982
Holmes, J.L.; Burgers, P.C.; Mollah, Y.A., Alkane elimination from ionized alkanols, Org. Mass Spectrom., 1982, 17, 127. [all data]

Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P., Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations, Can. J. Chem., 1981, 59, 80. [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]

Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L., Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Org. Mass Spectrom., 1982, 17, 123. [all data]

Holmes, Rye, et al., 1979
Holmes, J.L.; Rye, R.T.B.; Terlouw, J.K., On the loss of ethylene from [C₃H₇O]⁺ ions of structure CH₃CH₂CHOH, Org. Mass Spectrom., 1979, 14, 606. [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]

Holmes, Lossing, et al., 1988
Holmes, J.L.; Lossing, F.P.; Maccoll, A., Heats of formation of alkyl radicals from appearance energies, J. Am. Chem. Soc., 1988, 110, 7339. [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]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  IE (evaluated)	Recommended ionization energy
  S°gas	Entropy of gas at standard conditions
  ΔfH°gas	Enthalpy of formation of gas 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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