Trimethylamine, protonated

• Formula: C₃H₁₀N⁺
• Molecular weight: 60.1177
• Information on this page:
  • Reaction thermochemistry data
  • Ion clustering data
  • References
  • Notes
• Options:
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Reaction thermochemistry data

Go To: Top, Ion clustering data, References, Notes

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

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

(C₃H₁₀N⁺ • 3) +  = (C₃H₁₀N⁺ • 4)

By formula: (C₃H₁₀N⁺ • 3H₂O) + H₂O = (C₃H₁₀N⁺ • 4H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

Free energy of reaction

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + H₂O = (C₃H₁₀N⁺ • H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₃H₉N = (C₃H₁₀N⁺ • C₃H₉N)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₁₂H₂₄O₆ = (C₃H₁₀N⁺ • C₁₂H₂₄O₆)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Free energy of reaction

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • H₂O • C₃H₉N) + H₂O = (C₃H₁₀N⁺ • 2H₂O • C₃H₉N)

Free energy of reaction

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₄H₉NO = (C₃H₁₀N⁺ • C₄H₉NO)

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

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ • 3)

By formula: (C₃H₁₀N⁺ • 2H₂O) + H₂O = (C₃H₁₀N⁺ • 3H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ • 2)

By formula: (C₃H₁₀N⁺ • H₂O) + H₂O = (C₃H₁₀N⁺ • 2H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₈H₁₈O₄ = (C₃H₁₀N⁺ • C₈H₁₈O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₆H₁₄O₃ = (C₃H₁₀N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ •  • )

By formula: (C₃H₁₀N⁺ • C₃H₉N) + CH₄O = (C₃H₁₀N⁺ • CH₄O • C₃H₉N)

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

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ • 3)

By formula: (C₃H₁₀N⁺ • 2CH₄O) + CH₄O = (C₃H₁₀N⁺ • 3CH₄O)

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

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ •  • 2)

By formula: (C₃H₁₀N⁺ • 2C₃H₉N) + H₂O = (C₃H₁₀N⁺ • H₂O • 2C₃H₉N)

Bond type: Hydrogen bond (positive ion to hydride)

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ • 2)

By formula: (C₃H₁₀N⁺ • CH₄O) + CH₄O = (C₃H₁₀N⁺ • 2CH₄O)

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₅H₁₂O₂ = (C₃H₁₀N⁺ • C₅H₁₂O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₁₀H₂₀O₅ = (C₃H₁₀N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₄H₁₀O₂ = (C₃H₁₀N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₈H₁₆O₄ = (C₃H₁₀N⁺ • C₈H₁₆O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₆H₁₁NO₃ = (C₃H₁₀N⁺ • C₆H₁₁NO₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + CH₄O = (C₃H₁₀N⁺ • CH₄O)

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₅H₁₀O = (C₃H₁₀N⁺ • C₅H₁₀O)

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

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • CH₄O • C₃H₉N) + CH₄O = (C₃H₁₀N⁺ • 2CH₄O • C₃H₉N)

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₂H₇N = (C₃H₁₀N⁺ • C₂H₇N)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + CHN = (C₃H₁₀N⁺ • CHN)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₆H₆ = (C₃H₁₀N⁺ • C₆H₆)

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • C₃H₉N • H₂O) + C₃H₉N = (C₃H₁₀N⁺ • 2C₃H₉N • H₂O)

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ • 3)

By formula: (C₃H₁₀N⁺ • 2C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 3C₃H₉N)

(C₃H₁₀N⁺ • 3) +  = (C₃H₁₀N⁺ • 4)

By formula: (C₃H₁₀N⁺ • 3C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 4C₃H₉N)

(C₃H₁₀N⁺ • 4) +  = (C₃H₁₀N⁺ • 5)

By formula: (C₃H₁₀N⁺ • 4C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 5C₃H₉N)

(C₃H₁₀N⁺ • 5) +  = (C₃H₁₀N⁺ • 6)

By formula: (C₃H₁₀N⁺ • 5C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 6C₃H₉N)

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ • 2)

By formula: (C₃H₁₀N⁺ • C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 2C₃H₉N)

Ion clustering data

Go To: Top, Reaction thermochemistry data, References, Notes

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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + CHN = (C₃H₁₀N⁺ • CHN)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + CH₄O = (C₃H₁₀N⁺ • CH₄O)

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

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ • 2)

By formula: (C₃H₁₀N⁺ • CH₄O) + CH₄O = (C₃H₁₀N⁺ • 2CH₄O)

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

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ • 3)

By formula: (C₃H₁₀N⁺ • 2CH₄O) + CH₄O = (C₃H₁₀N⁺ • 3CH₄O)

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

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • CH₄O • C₃H₉N) + CH₄O = (C₃H₁₀N⁺ • 2CH₄O • C₃H₉N)

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₂H₇N = (C₃H₁₀N⁺ • C₂H₇N)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₃H₉N = (C₃H₁₀N⁺ • C₃H₉N)

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ •  • )

By formula: (C₃H₁₀N⁺ • C₃H₉N) + CH₄O = (C₃H₁₀N⁺ • CH₄O • C₃H₉N)

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

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ • 2)

By formula: (C₃H₁₀N⁺ • C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 2C₃H₉N)

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ • 3)

By formula: (C₃H₁₀N⁺ • 2C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 3C₃H₉N)

(C₃H₁₀N⁺ • 3) +  = (C₃H₁₀N⁺ • 4)

By formula: (C₃H₁₀N⁺ • 3C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 4C₃H₉N)

(C₃H₁₀N⁺ • 4) +  = (C₃H₁₀N⁺ • 5)

By formula: (C₃H₁₀N⁺ • 4C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 5C₃H₉N)

(C₃H₁₀N⁺ • 5) +  = (C₃H₁₀N⁺ • 6)

By formula: (C₃H₁₀N⁺ • 5C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 6C₃H₉N)

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ •  • 2)

By formula: (C₃H₁₀N⁺ • 2C₃H₉N) + H₂O = (C₃H₁₀N⁺ • H₂O • 2C₃H₉N)

Bond type: Hydrogen bond (positive ion to hydride)

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • C₃H₉N • H₂O) + C₃H₉N = (C₃H₁₀N⁺ • 2C₃H₉N • H₂O)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₄H₉NO = (C₃H₁₀N⁺ • C₄H₉NO)

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₄H₁₀O₂ = (C₃H₁₀N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₅H₁₀O = (C₃H₁₀N⁺ • C₅H₁₀O)

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₅H₁₂O₂ = (C₃H₁₀N⁺ • C₅H₁₂O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₆H₆ = (C₃H₁₀N⁺ • C₆H₆)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₆H₁₁NO₃ = (C₃H₁₀N⁺ • C₆H₁₁NO₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₆H₁₄O₃ = (C₃H₁₀N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₈H₁₆O₄ = (C₃H₁₀N⁺ • C₈H₁₆O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₈H₁₈O₄ = (C₃H₁₀N⁺ • C₈H₁₈O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₁₀H₂₀O₅ = (C₃H₁₀N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₁₂H₂₄O₆ = (C₃H₁₀N⁺ • C₁₂H₂₄O₆)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Free energy of reaction

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + H₂O = (C₃H₁₀N⁺ • H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • H₂O • C₃H₉N) + H₂O = (C₃H₁₀N⁺ • 2H₂O • C₃H₉N)

Free energy of reaction

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ • 2)

By formula: (C₃H₁₀N⁺ • H₂O) + H₂O = (C₃H₁₀N⁺ • 2H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ • 3)

By formula: (C₃H₁₀N⁺ • 2H₂O) + H₂O = (C₃H₁₀N⁺ • 3H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₃H₁₀N⁺ • 3) +  = (C₃H₁₀N⁺ • 4)

By formula: (C₃H₁₀N⁺ • 3H₂O) + H₂O = (C₃H₁₀N⁺ • 4H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

Free energy of reaction

References

Go To: Top, Reaction thermochemistry data, 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 (Mautner), 1984
Meot-Ner (Mautner), M., The Ionic Hydrogen Bond and Ion Solvation. 2. Hydration of Onium Ions by 1 - 7 H2O Molecules. Relations Between Monomolecular, Specific and Bulk Hydration, J. Am. Chem. Soc., 1984, 106, 5, 1265, https://doi.org/10.1021/ja00317a016 . [all data]

El-Shall, Daly, et al., 1992
El-Shall, M.S.; Daly, G.M.; Gao, J.; Meot-Ner (Mautner), M.; Sieck, L.W., How Sensitive are Cluster Compositions to Energetics? A Joint Beam Expansion/ Thermochemical Study of Water - Methanol - Trimethylamine Clusters, J. Phys. Chem., 1992, 96, 2, 507, https://doi.org/10.1021/j100181a002 . [all data]

Meot-Ner M. and Sieck, 1983
Meot-Ner M.; Sieck, L.W., The Ionic Hydrogen Bond. 1. Sterically Hindered Bonds. Solvation and Clustering of Sterically Hindered Amines and Pyridines, J. Am. Chem. Soc., 1983, 105, 10, 2956, https://doi.org/10.1021/ja00348a005 . [all data]

Banic and Iribarne, 1985
Banic, C.M.; Iribarne, J.V., Equilibrium Constants for Clustering of Neutral Molecules about Gaseous Ions, J. Chem. Phys., 1985, 83, 12, 6432, https://doi.org/10.1063/1.449543 . [all data]

Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M., Intermolecular Forces in Organic Clusters, J. Am. Chem. Soc., 1992, 114, 9, 3312, https://doi.org/10.1021/ja00035a024 . [all data]

Wei, Tzeng, et al., 1991
Wei, S.; Tzeng, W.B.; Castleman, A.W., Structure of protonated solvation complexes - ammonia trimethylamine cluster ions and their metastable decompositions, J. Phys. Chem., 1991, 95, 2, 585, https://doi.org/10.1021/j100155a019 . [all data]

Yamdagni and Kebarle, 1973
Yamdagni, R.; Kebarle, P., Gas - Phase Basicites of Amines. Hydrogen Bonding in Proton - Bound Amine Dimers and Proton - Induced Cyclization of alpha, omega - Diamines, J. Am. Chem. Soc., 1973, 95, 11, 3504, https://doi.org/10.1021/ja00792a010 . [all data]

Meot-Ner (Mautner), 1983
Meot-Ner (Mautner), M., The Ionic Hydrogen Bond. 3. Multiple and -CH+...O- Bonds. Complexes of Ammonium Ions with Polyethers and Crown Ethers, J. Am. Chem. Soc., 1983, 105, 15, 4912, https://doi.org/10.1021/ja00353a012 . [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]

Meot-Ner, 1984, 2
Meot-Ner, (Mautner), The Ionic Hydrogen Bond. 4. Intramolecular and Multiple Bonds. Proton Affinities, Hydration and Complexes of Amides and Amino Acid Derivatives, J. Am. Chem. Soc., 1984, 106, 2, 278, https://doi.org/10.1021/ja00314a003 . [all data]

Speller and Meot-Ner (Mautner), 1985
Speller, C.V.; Meot-Ner (Mautner), M., The Ionic Hydrogen Bond and Ion Solvation. 3. Bonds Involving Cyanides. Correlations with Proton Affinites, J. Phys. Chem., 1985, 81, 24, 5217, https://doi.org/10.1021/j100270a020 . [all data]

Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M., Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives, J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034 . [all data]

Notes

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• 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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