Pyridine, protonated


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 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

C5H6N+ + Pyridine = (C5H6N+ • Pyridine)

By formula: C5H6N+ + C5H5N = (C5H6N+ • C5H5N)

Quantity Value Units Method Reference Comment
Δr25.2kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase
Δr24.6kcal/molPHPMSMeot-Ner M. and Sieck, 1983gas phase
Δr26.3kcal/molHPMSHolland and Castleman, 1982gas phase
Δr23.7kcal/molPHPMSMeot-Ner (Mautner), 1979gas phase
Δr23.7kcal/molPHPMSMeot-Ner (Mautner), 1979gas phase
Quantity Value Units Method Reference Comment
Δr29.6cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase
Δr28.2cal/mol*KPHPMSMeot-Ner M. and Sieck, 1983gas phase
Δr32.1cal/mol*KHPMSHolland and Castleman, 1982gas phase
Δr28.cal/mol*KPHPMSMeot-Ner (Mautner), 1979gas phase
Δr28.cal/mol*KPHPMSMeot-Ner (Mautner), 1979gas phase

C5H6N+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C5H6N+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C5H6N+ + C12H24O6 = (C5H6N+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr42. ± 4.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Δr44.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
16.550.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated

C5H6N+ + Di-n-propyl ether = (C5H6N+ • Di-n-propyl ether)

By formula: C5H6N+ + C6H14O = (C5H6N+ • C6H14O)

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
Quantity Value Units Method Reference Comment
Δr31.cal/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
8.0500.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated

C5H6N+ + Water = (C5H6N+ • Water)

By formula: C5H6N+ + H2O = (C5H6N+ • H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr16.1kcal/molPHPMSMeot-Ner M. and Sieck, 1983gas phase
Δr15.0kcal/molPHPMSDavidson, Sunner J., et al., 1979gas phase
Quantity Value Units Method Reference Comment
Δr27.0cal/mol*KPHPMSMeot-Ner M. and Sieck, 1983gas phase
Δr25.5cal/mol*KPHPMSDavidson, Sunner J., et al., 1979gas phase

C5H6N+ + Ethane, 1,1'-oxybis[2-methoxy- = (C5H6N+ • Ethane, 1,1'-oxybis[2-methoxy-)

By formula: C5H6N+ + C6H14O3 = (C5H6N+ • C6H14O3)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr31.5kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; diglyme
Quantity Value Units Method Reference Comment
Δr36.5cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; diglyme

C5H6N+ + Ethane, 1,2-dimethoxy- = (C5H6N+ • Ethane, 1,2-dimethoxy-)

By formula: C5H6N+ + C4H10O2 = (C5H6N+ • C4H10O2)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr25.4kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; glyme
Quantity Value Units Method Reference Comment
Δr31.4cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; glyme

(C5H6N+ • 2Pyridine) + Pyridine = (C5H6N+ • 3Pyridine)

By formula: (C5H6N+ • 2C5H5N) + C5H5N = (C5H6N+ • 3C5H5N)

Quantity Value Units Method Reference Comment
Δr13.6kcal/molHPMSHolland and Castleman, 1982gas phase; Entropy change is questionable
Quantity Value Units Method Reference Comment
Δr37.9cal/mol*KHPMSHolland and Castleman, 1982gas phase; Entropy change is questionable

(C5H6N+ • 2Water) + Water = (C5H6N+ • 3Water)

By formula: (C5H6N+ • 2H2O) + H2O = (C5H6N+ • 3H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr8.3kcal/molPHPMSDavidson, Sunner J., et al., 1979gas phase
Quantity Value Units Method Reference Comment
Δr19.6cal/mol*KPHPMSDavidson, Sunner J., et al., 1979gas phase

C5H6N+ + Propane, 1,3-dimethoxy- = (C5H6N+ • Propane, 1,3-dimethoxy-)

By formula: C5H6N+ + C5H12O2 = (C5H6N+ • C5H12O2)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr26.5kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Δr35.8cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

C5H6N+ + 15-Crown-5 = (C5H6N+ • 15-Crown-5)

By formula: C5H6N+ + C10H20O5 = (C5H6N+ • C10H20O5)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr41.0kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Δr42.6cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

(C5H6N+ • Water) + Water = (C5H6N+ • 2Water)

By formula: (C5H6N+ • H2O) + H2O = (C5H6N+ • 2H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr9.6kcal/molPHPMSDavidson, Sunner J., et al., 1979gas phase
Quantity Value Units Method Reference Comment
Δr19.6cal/mol*KPHPMSDavidson, Sunner J., et al., 1979gas phase

C5H6N+ + 2,5,8,11-Tetraoxadodecane = (C5H6N+ • 2,5,8,11-Tetraoxadodecane)

By formula: C5H6N+ + C8H18O4 = (C5H6N+ • C8H18O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr34.7kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Δr38.3cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

C5H6N+ + 12-Crown-4 = (C5H6N+ • 12-Crown-4)

By formula: C5H6N+ + C8H16O4 = (C5H6N+ • C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr36.1kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Δr40.0cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

C5H6N+ + Ethyl ether = (C5H6N+ • Ethyl ether)

By formula: C5H6N+ + C4H10O = (C5H6N+ • C4H10O)

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

Quantity Value Units Method Reference Comment
Δr22.5kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Δr32.9cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

(C5H6N+ • Pyridine) + Pyridine = (C5H6N+ • 2Pyridine)

By formula: (C5H6N+ • C5H5N) + C5H5N = (C5H6N+ • 2C5H5N)

Quantity Value Units Method Reference Comment
Δr12.6kcal/molHPMSHolland and Castleman, 1982gas phase
Quantity Value Units Method Reference Comment
Δr29.7cal/mol*KHPMSHolland and Castleman, 1982gas phase

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.

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]

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]

Holland and Castleman, 1982
Holland, P.M.; Castleman, A.W., The Thermochemical Properties of Gas - Phase Transition Metal Ion Complexes, J. Chem. Phys., 1982, 76, 8, 4195, https://doi.org/10.1063/1.443497 . [all data]

Meot-Ner (Mautner), 1979
Meot-Ner (Mautner), M., Ion Thermochemistry of Low Volatility Compounds in the Gas Phase. II. Intrinsic Basicities and Hydrogen Bonded Dimers of Nitrogen Heterocyclics and Nucleic Bases, J. Am. Chem. Soc., 1979, 101, 9, 2396, https://doi.org/10.1021/ja00503a027 . [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]

Davidson, Sunner J., et al., 1979
Davidson, W.R.; Sunner J.; Kebarle, P., Hydrogen Bonding of Water to Onium Ions. Hydration of Substituted Pyridinium Ions and Related Systems, J. Am. Chem. Soc., 1979, 101, 7, 1675, https://doi.org/10.1021/ja00501a005 . [all data]


Notes

Go To: Top, Reaction thermochemistry data, References