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Pyridine, 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

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

C5H6N+ + Ethyl ether = (C5H6N+ bullet Ethyl ether)

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

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

Quantity Value Units Method Reference Comment
Deltar94.1kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Deltar138.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

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

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar106.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; glyme
Quantity Value Units Method Reference Comment
Deltar131.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; glyme

C5H6N+ + Pyridine = (C5H6N+ bullet Pyridine)

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

Quantity Value Units Method Reference Comment
Deltar105.kJ/molPHPMSMeot-Ner (Mautner), 1992gas phase
Deltar103.kJ/molPHPMSMeot-Ner M. and Sieck, 1983gas phase
Deltar110.kJ/molHPMSHolland and Castleman, 1982gas phase
Deltar99.2kJ/molPHPMSMeot-Ner (Mautner), 1979gas phase
Deltar99.2kJ/molPHPMSMeot-Ner (Mautner), 1979gas phase
Quantity Value Units Method Reference Comment
Deltar124.J/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase
Deltar118.J/mol*KPHPMSMeot-Ner M. and Sieck, 1983gas phase
Deltar134.J/mol*KHPMSHolland and Castleman, 1982gas phase
Deltar120.J/mol*KPHPMSMeot-Ner (Mautner), 1979gas phase
Deltar120.J/mol*KPHPMSMeot-Ner (Mautner), 1979gas phase

(C5H6N+ bullet Pyridine) + Pyridine = (C5H6N+ bullet 2Pyridine)

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

Quantity Value Units Method Reference Comment
Deltar52.7kJ/molHPMSHolland and Castleman, 1982gas phase
Quantity Value Units Method Reference Comment
Deltar124.J/mol*KHPMSHolland and Castleman, 1982gas phase

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

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

Quantity Value Units Method Reference Comment
Deltar56.9kJ/molHPMSHolland and Castleman, 1982gas phase; Entropy change is questionable
Quantity Value Units Method Reference Comment
Deltar159.J/mol*KHPMSHolland and Castleman, 1982gas phase; Entropy change is questionable

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

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar111.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Deltar150.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

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

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

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

Quantity Value Units Method Reference Comment
Deltar98.3kJ/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Deltar130.J/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated

Free energy of reaction

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

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

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar132.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; diglyme
Quantity Value Units Method Reference Comment
Deltar153.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; diglyme

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

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar151.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Deltar167.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

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

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar145.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Deltar160.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

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

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar172.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase
Quantity Value Units Method Reference Comment
Deltar178.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase

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

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar180. ± 20.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Deltar180.J/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated

Free energy of reaction

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

C5H6N+ + Water = (C5H6N+ bullet Water)

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

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar67.4kJ/molPHPMSMeot-Ner M. and Sieck, 1983gas phase
Deltar62.8kJ/molPHPMSDavidson, Sunner J., et al., 1979gas phase
Quantity Value Units Method Reference Comment
Deltar113.J/mol*KPHPMSMeot-Ner M. and Sieck, 1983gas phase
Deltar107.J/mol*KPHPMSDavidson, Sunner J., et al., 1979gas phase

(C5H6N+ bullet Water) + Water = (C5H6N+ bullet 2Water)

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

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar40.kJ/molPHPMSDavidson, Sunner J., et al., 1979gas phase
Quantity Value Units Method Reference Comment
Deltar82.0J/mol*KPHPMSDavidson, Sunner J., et al., 1979gas phase

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

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

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar35.kJ/molPHPMSDavidson, Sunner J., et al., 1979gas phase
Quantity Value Units Method Reference Comment
Deltar82.0J/mol*KPHPMSDavidson, Sunner J., et al., 1979gas phase

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 (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 (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, 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

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