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1-Butanol

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Ion clustering 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar

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Clustering reactions

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

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

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

Quantity Value Units Method Reference Comment
Deltar23.5kcal/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Free energy of reaction

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

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

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

Quantity Value Units Method Reference Comment
Deltar44.2kcal/molPHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar31.1cal/mol*KN/AWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (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+ bullet 1-Butanol)

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

Quantity Value Units Method Reference Comment
Deltar36.5kcal/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar32.4cal/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (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

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

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

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

Quantity Value Units Method Reference Comment
Deltar31.5kcal/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
Deltar30.9cal/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
Deltar22.3kcal/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

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

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

Quantity Value Units Method Reference Comment
Deltar14.6kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar25.0cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar17.6 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar23.2cal/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
Deltar10.7 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M

Fluorine anion + 1-Butanol = C4H9D10FO-

By formula: F- + C4H10O = C4H9D10FO-

Quantity Value Units Method Reference Comment
Deltar24.1 ± 2.0kcal/molIMREWilkinson, Szulejko, et al., 1992gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B

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

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

Quantity Value Units Method Reference Comment
Deltar32.2 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar25.9cal/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
Deltar24.5 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B,M

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

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

Quantity Value Units Method Reference Comment
Deltar42.5 ± 1.9kcal/molCIDTRodgers and Armentrout, 2000RCD

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

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

Quantity Value Units Method Reference Comment
Deltar65. ± 5.kcal/molICROperti, Tews, et al., 1988gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M

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

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

Quantity Value Units Method Reference Comment
Deltar26.1 ± 1.2kcal/molCIDTRodgers and Armentrout, 1999RCD

Free energy of reaction

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

References

Go To: Top, Ion clustering data, Notes

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

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]

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]

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]

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]

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]

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]

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]

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]

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]

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]


Notes

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