1-Butanol

• Formula: C₄H₁₀O
• Molecular weight: 74.1216
• IUPAC Standard InChI: InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 Copy

  
• IUPAC Standard InChIKey: LRHPLDYGYMQRHN-UHFFFAOYSA-N Copy
• CAS Registry Number: 71-36-3
• 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: Butyl alcohol; n-Butan-1-ol; n-Butanol; n-Butyl alcohol; Butyl hydroxide; CCS 203; Hemostyp; Methylolpropane; Propylcarbinol; n-C4H9OH; Butanol; Butan-1-ol; 1-Hydroxybutane; Alcool butylique; Butanolo; Butylowy alkohol; Butyric alcohol; Propylmethanol; Butanolen; 1-Butyl alcohol; Rcra waste number U031; Butanol-1; NSC 62782
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• 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

C₄H₉O^- +  =

By formula: C₄H₉O^- + H⁺ = C₄H₁₀O

C₄H₁₁O⁺ +  = (C₄H₁₁O⁺ • )

By formula: C₄H₁₁O⁺ + C₄H₁₀O = (C₄H₁₁O⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₄H₁₀O = (C₃H₉Si⁺ • C₄H₁₀O)

Free energy of reaction

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

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

Free energy of reaction

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: F^- + C₄H₁₀O = (F^- • C₄H₁₀O)

 +  = ( • )

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

 +  = ( • )

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

Free energy of reaction

 +  =

By formula: C₄H₈O + H₂ = C₄H₁₀O

 +  = ( • )

By formula: C₆H₅S^- + C₄H₁₀O = (C₆H₅S^- • C₄H₁₀O)

 +  =

By formula: C₇H₅NO + C₄H₁₀O = C₁₁H₁₅NO₂

 +  = C₄H₉D₁₀FO^-

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

 +  = ( • )

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

 +  =  + 

By formula: C₄H₁₀O + ClHO₃S = C₄H₁₀O₄S + HCl

 +  =  + 

By formula: C₄H₁₀O + C₃H₄O₂ = C₇H₁₂O₂ + H₂O

 +  =  + 

By formula: C₆H₁₂O₂ + H₂O = C₂H₄O₂ + C₄H₁₀O

 +  =

By formula: C₄H₂O₃ + C₄H₁₀O = C₈H₁₂O₄

 +  =

By formula: C₄H₈ + C₄H₁₀O = C₈H₁₈O

 +  =

By formula: C₂H₂O + C₄H₁₀O = C₆H₁₂O₂

 +  = ( • )

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.

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]

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]

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]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [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]

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]

Larson and McMahon, 1984
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]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [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]

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Buckley and Cox, 1967
Buckley, E.; Cox, J.D., Chemical equilibria. Part 2.-Dehydrogenation of propanol and butanol, Trans. Faraday Soc., 1967, 63, 895-901. [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]

Pannone and Macosko, 1987
Pannone, M.C.; Macosko, C.W., Kinetics of isocyanate amine reactions, J. Appl. Polym. Sci., 1987, 34, 2409-2432. [all data]

Lovering and Laidler, 1962
Lovering, E.G.; Laidler, K.J., Thermochemical studies of some alcohol-isocyanate reactions, Can. J. Chem., 1962, 40, 26-30. [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]

Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Markitanova, Barsukov, et al., 1981
Markitanova, L.I.; Barsukov, I.I.; Passet, B.V., Determination of heat of sulfation by calorimetric titration, J. Gen. Chem. USSR, 1981, 51, 1286-1289. [all data]

Selyakova, Vytnov, et al., 1976
Selyakova, V.A.; Vytnov, G.F.; Sineokov, A.P., Study of the esterification of acrylic acid by butyl alcohol, Russ. J. Phys. Chem. (Engl. Transl.), 1976, 50, 1692-1694. [all data]

Wadso, 1958
Wadso, I., The heats of hydrolysis of some alkyl acetates, Acta Chem. Scand., 1958, 12, 630-633. [all data]

Merca, Poraicu, et al., 1978
Merca, E.; Poraicu, M.; Tribunescu, P., Kinetics of maleic monoester formation with n-butanol, Bull. Stiint. Teh. Inst. Politeh. "Traian Vuia" Timisoara, Ser. Chim., 1978, 23, 160-163. [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, 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]

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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