1-Butanol

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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
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- + Hydrogen cation = 1-Butanol

By formula: C4H9O- + H+ = C4H10O

Quantity Value Units Method Reference Comment
Δr375.3 ± 2.0kcal/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Δr375.4 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr375.0 ± 2.9kcal/molG+TSBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr368.7 ± 2.1kcal/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Δr368.8 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr368.4 ± 2.8kcal/molCIDCBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale; B

C4H11O+ + 1-Butanol = (C4H11O+ • 1-Butanol)

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

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

Quantity Value Units Method Reference Comment
Δr31.5kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity Value Units Method Reference Comment
Δr30.9cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity Value Units Method Reference Comment
Δr22.3kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M

C3H9Si+ + 1-Butanol = (C3H9Si+ • 1-Butanol)

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

Quantity Value Units Method Reference Comment
Δr44.2kcal/molPHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr31.1cal/mol*KN/AWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
29.7468.PHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M

C3H9Sn+ + 1-Butanol = (C3H9Sn+ • 1-Butanol)

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

Quantity Value Units Method Reference Comment
Δr36.5kcal/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr32.4cal/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
19.5525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

CH6N+ + 1-Butanol = (CH6N+ • 1-Butanol)

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

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

Quantity Value Units Method Reference Comment
Δr23.5kcal/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr26.cal/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
10.6495.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Fluorine anion + 1-Butanol = (Fluorine anion • 1-Butanol)

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

Quantity Value Units Method Reference Comment
Δr32.2 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B,M
Quantity Value Units Method Reference Comment
Δr25.9cal/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Δr24.5 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B,M

Chlorine anion + 1-Butanol = (Chlorine anion • 1-Butanol)

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

Quantity Value Units Method Reference Comment
Δr17.6 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Δr23.2cal/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)CH3OH, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Δr10.7 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M

Sodium ion (1+) + 1-Butanol = (Sodium ion (1+) • 1-Butanol)

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

Quantity Value Units Method Reference Comment
Δr26.1 ± 1.2kcal/molCIDTRodgers and Armentrout, 1999RCD

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
19.7298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

Butanal + Hydrogen = 1-Butanol

By formula: C4H8O + H2 = C4H10O

Quantity Value Units Method Reference Comment
Δr-19.57 ± 0.18kcal/molCmWiberg, Crocker, et al., 1991liquid phase; ALS
Δr-16.85 ± 0.30kcal/molChydBuckley and Cox, 1967gas phase; ALS

thiophenoxide anion + 1-Butanol = (thiophenoxide anion • 1-Butanol)

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

Quantity Value Units Method Reference Comment
Δr14.6kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr25.0cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

Benzene, isocyanato- + 1-Butanol = Carbamic acid, phenyl-, butyl ester

By formula: C7H5NO + C4H10O = C11H15NO2

Quantity Value Units Method Reference Comment
Δr-20.1 ± 1.1kcal/molCmPannone and Macosko, 1987liquid phase; ALS
Δr-25.1 ± 0.3kcal/molCmLovering and Laidler, 1962solid phase; ALS

Fluorine anion + 1-Butanol = C4H9D10FO-

By formula: F- + C4H10O = C4H9D10FO-

Quantity Value Units Method Reference Comment
Δr24.1 ± 2.0kcal/molIMREWilkinson, Szulejko, et al., 1992gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B

Magnesium ion (1+) + 1-Butanol = (Magnesium ion (1+) • 1-Butanol)

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

Quantity Value Units Method Reference Comment
Δr65. ± 5.kcal/molICROperti, Tews, et al., 1988gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M

1-Butanol + Chloridosulfuric acid = Butyl sulfuric acid + Hydrogen chloride

By formula: C4H10O + ClHO3S = C4H10O4S + HCl

Quantity Value Units Method Reference Comment
Δr14. ± 0.2kcal/molCmMarkitanova, Barsukov, et al., 1981liquid phase; solvent: Dichloromethane; Sulfation; ALS

1-Butanol + 2-Propenoic acid = 2-Propenoic acid, butyl ester + Water

By formula: C4H10O + C3H4O2 = C7H12O2 + H2O

Quantity Value Units Method Reference Comment
Δr3.9kcal/molEqkSelyakova, Vytnov, et al., 1976liquid phase; Heat of esterification 60-180 C; ALS

Acetic acid, butyl ester + Water = Acetic acid + 1-Butanol

By formula: C6H12O2 + H2O = C2H4O2 + C4H10O

Quantity Value Units Method Reference Comment
Δr0.80 ± 0.05kcal/molCmWadso, 1958liquid phase; Heat of hydrolysis; ALS

Maleic anhydride + 1-Butanol = 2-Butenedioic acid (Z)-, monobutyl ester

By formula: C4H2O3 + C4H10O = C8H12O4

Quantity Value Units Method Reference Comment
Δr-9.3kcal/molKinMerca, Poraicu, et al., 1978solid phase; solvent: n-Butanol; DTA; ALS

1-Propene, 2-methyl- + 1-Butanol = 1-Tert-butoxybutane

By formula: C4H8 + C4H10O = C8H18O

Quantity Value Units Method Reference Comment
Δr-8.32 ± 0.65kcal/molEqkSharonov, Mishentseva, et al., 1991liquid phase; ALS

Ketene + 1-Butanol = Acetic acid, butyl ester

By formula: C2H2O + C4H10O = C6H12O2

Quantity Value Units Method Reference Comment
Δr-35.11kcal/molCmRice and Greenberg, 1934liquid phase; ALS

Lithium ion (1+) + 1-Butanol = (Lithium ion (1+) • 1-Butanol)

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

Quantity Value Units Method Reference Comment
Δr42.5 ± 1.9kcal/molCIDTRodgers and Armentrout, 2000RCD

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

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