Di-n-propyl ether, protonated


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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Clustering reactions

C6H15O+ + Acetonitrile = (C6H15O+ • Acetonitrile)

By formula: C6H15O+ + C2H3N = (C6H15O+ • C2H3N)

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
18.7320.ICRBromilow, Abboud, et al., 1980gas phase; switching reaction,n((CH3)2OH+)(CH3)2O; Grimsrud and Kebarle, 1973

C6H15O+ + Ethyl ether = (C6H15O+ • Ethyl ether)

By formula: C6H15O+ + C4H10O = (C6H15O+ • C4H10O)

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

Quantity Value Units Method Reference Comment
Δr29.3kcal/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, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Δr30.0cal/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, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Δr20.4kcal/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, Keesee and Castleman, 1986

C6H15O+ + Di-n-propyl ether = (C6H15O+ • Di-n-propyl ether)

By formula: C6H15O+ + C6H14O = (C6H15O+ • C6H14O)

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

Bond type: Hydrogen bonds between protonated and neutral organics

Quantity Value Units Method Reference Comment
Δr30.9kcal/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase; switching reaction(C2H5)COH+((C2H5)2CO
Δr29.9kcal/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, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Δr40.0cal/mol*KPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase; switching reaction(C2H5)COH+((C2H5)2CO
Δr31.9cal/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, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Δr20.4kcal/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, Keesee and Castleman, 1986

C6H15O+ + Water = (C6H15O+ • Water)

By formula: C6H15O+ + H2O = (C6H15O+ • H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr18.8kcal/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase
Quantity Value Units Method Reference Comment
Δr28.4cal/mol*KPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase

(C6H15O+ • Water) + Water = (C6H15O+ • 2Water)

By formula: (C6H15O+ • H2O) + H2O = (C6H15O+ • 2H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr13.2kcal/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase
Quantity Value Units Method Reference Comment
Δr25.7cal/mol*KPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase

(C6H15O+ • 2Water) + Water = (C6H15O+ • 3Water)

By formula: (C6H15O+ • 2H2O) + H2O = (C6H15O+ • 3H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr12.5kcal/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase
Quantity Value Units Method Reference Comment
Δr27.0cal/mol*KPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase

(C6H15O+ • 3Water) + Water = (C6H15O+ • 4Water)

By formula: (C6H15O+ • 3H2O) + H2O = (C6H15O+ • 4H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr10.5kcal/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase
Quantity Value Units Method Reference Comment
Δr23.7cal/mol*KPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase

(C6H15O+ • 4Water) + Water = (C6H15O+ • 5Water)

By formula: (C6H15O+ • 4H2O) + H2O = (C6H15O+ • 5H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr10.2kcal/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase
Quantity Value Units Method Reference Comment
Δr25.3cal/mol*KPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase

(C6H15O+ • 5Water) + Water = (C6H15O+ • 6Water)

By formula: (C6H15O+ • 5H2O) + H2O = (C6H15O+ • 6H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr9.4kcal/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Δr25.0cal/mol*KN/AMeot-Ner (Mautner), Sieck, et al., 1994gas phase; Entropy change calculated or estimated

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
3.5234.PHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase; Entropy change calculated or estimated

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.

Bromilow, Abboud, et al., 1980
Bromilow, J.; Abboud, J.L.M.; Lebrilla, C.B.; Taft, R.W.; Scorrano, G.; Lucchini, V., Oxonium Ions. Solvation by Single Acetonitrile Molecules in the Gas Phase and by Bulk Solvents, J. Am. Chem. Soc., 1980, 103, 18, 5448, https://doi.org/10.1021/ja00408a028 . [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]

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]

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]

Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Meot-Ner (Mautner), Sieck, et al., 1994
Meot-Ner (Mautner), M.; Sieck, L.W.; Liebman, J.F.; Scheiner, S.; Duan, X., The Ionic Hydrogen Bond. 5. Polydentate and Solvent-Bridged Structures. Complexing of the Proton and the Hydronium Ions by Polyethers, J. Am. Chem. Soc., 1994, 116, 17, 7848, https://doi.org/10.1021/ja00096a047 . [all data]


Notes

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