Pyridine

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Reaction thermochemistry 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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

C5H4N- + Hydrogen cation = Pyridine

By formula: C5H4N- + H+ = C5H5N

Quantity Value Units Method Reference Comment
Δr389.9 ± 2.0kcal/molIMRESchafman and Wenthold, 2007gas phase; B
Δr391.0 ± 2.5kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Quantity Value Units Method Reference Comment
Δr382.7 ± 2.0kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Δr384.0 ± 3.0kcal/molIMRBDePuy, Kass, et al., 1988gas phase; Comparable to water in acidity; B
Δr<376.3 ± 2.0kcal/molIMRBBruins, Ferrer-Correia, et al., 1978gas phase; O- deprotonates; B

C5H6N+ + Pyridine = (C5H6N+ • Pyridine)

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

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

Pyridine + 3Hydrogen = Piperidine

By formula: C5H5N + 3H2 = C5H11N

Quantity Value Units Method Reference Comment
Δr-46.31 ± 0.18kcal/molEqkHales and Herington, 1957gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -48.32 ± 0.18 kcal/mol; At 400-550 K; ALS
Δr-46.12 ± 0.50kcal/molEqkBurrows and King, 1935liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -45.00 kcal/mol; At 423-443 K; ALS

Chlorine anion + Pyridine = (Chlorine anion • Pyridine)

By formula: Cl- + C5H5N = (Cl- • C5H5N)

Quantity Value Units Method Reference Comment
Δr12.7 ± 2.0kcal/molTDAsHiraoka, Mizuse, et al., 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr19.7cal/mol*KPHPMSHiraoka, Mizuse, et al., 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr6.8 ± 2.6kcal/molTDAsHiraoka, Mizuse, et al., 1988gas phase; B

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

Lithium ion (1+) + Pyridine = (Lithium ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr43.2 ± 3.5kcal/molCIDTAmunugama and Rodgers, 2000RCD
Δr44.kcal/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M

Potassium ion (1+) + Pyridine = (Potassium ion (1+) • Pyridine)

By formula: K+ + C5H5N = (K+ • C5H5N)

Quantity Value Units Method Reference Comment
Δr21.6 ± 0.9kcal/molCIDTAmunugama and Rodgers, 2000RCD
Δr20.7kcal/molHPMSDavidson and Kebarle, 1976gas phase; M
Quantity Value Units Method Reference Comment
Δr18.6cal/mol*KHPMSDavidson and Kebarle, 1976gas phase; M

(Silver ion (1+) • 2Pyridine) + Pyridine = (Silver ion (1+) • 3Pyridine)

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

Quantity Value Units Method Reference Comment
Δr16.7kcal/molHPMSHolland and Castleman, 1982gas phase; M
Quantity Value Units Method Reference Comment
Δr28.0cal/mol*KHPMSHolland and Castleman, 1982gas phase; M

(Silver ion (1+) • 3Pyridine) + Pyridine = (Silver ion (1+) • 4Pyridine)

By formula: (Ag+ • 3C5H5N) + C5H5N = (Ag+ • 4C5H5N)

Quantity Value Units Method Reference Comment
Δr17.9kcal/molHPMSHolland and Castleman, 1982gas phase; M
Quantity Value Units Method Reference Comment
Δr40.3cal/mol*KHPMSHolland and Castleman, 1982gas phase; M

(Chlorine anion • Pyridine) + Pyridine = (Chlorine anion • 2Pyridine)

By formula: (Cl- • C5H5N) + C5H5N = (Cl- • 2C5H5N)

Quantity Value Units Method Reference Comment
Δr11.7kcal/molPHPMSHiraoka, Mizuse, et al., 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr22.6cal/mol*KPHPMSHiraoka, Mizuse, et al., 1988gas phase; M

(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; M
Quantity Value Units Method Reference Comment
Δr29.7cal/mol*KHPMSHolland and Castleman, 1982gas phase; M

H2O3- + Pyridine + Water = C5H7NO3-

By formula: H2O3- + C5H5N + H2O = C5H7NO3-

Quantity Value Units Method Reference Comment
Δr32.7 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

Oxygen anion + Pyridine = C5H5NO2-

By formula: O2- + C5H5N = C5H5NO2-

Quantity Value Units Method Reference Comment
Δr21.7 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

Nitric oxide anion + Pyridine = C5H5N2O-

By formula: NO- + C5H5N = C5H5N2O-

Quantity Value Units Method Reference Comment
Δr13.6 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

3Pyridine, 1-oxide + potassium chloride = 3Pyridine + KClO3

By formula: 3C5H5NO + ClK = 3C5H5N + KClO3

Quantity Value Units Method Reference Comment
Δr75.2 ± 2.4kcal/molCmShaofeng and Pilcher, 1988solid phase; ALS

3Pyridine, 1-oxide + potassium bromide = 3Pyridine + KBrO3

By formula: 3C5H5NO + BrK = 3C5H5N + KBrO3

Quantity Value Units Method Reference Comment
Δr75.0 ± 2.3kcal/molCmShaofeng and Pilcher, 1988solid phase; ALS

Iron ion (1+) + Pyridine = (Iron ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr53.4 ± 2.2kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Chromium ion (1+) + Pyridine = (Chromium ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr47.1 ± 2.8kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Titanium ion (1+) + Pyridine = (Titanium ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr51.9 ± 2.3kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Manganese ion (1+) + Pyridine = (Manganese ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr43.4 ± 2.1kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Scandium ion (1+) + Pyridine = (Scandium ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr55.3 ± 2.5kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Magnesium ion (1+) + Pyridine = (Magnesium ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr47.8 ± 1.6kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Vanadium ion (1+) + Pyridine = (Vanadium ion (1+) • Pyridine)

By formula: V+ + C5H5N = (V+ • C5H5N)

Quantity Value Units Method Reference Comment
Δr52.2 ± 3.2kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Nickel ion (1+) + Pyridine = (Nickel ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr60.9 ± 3.7kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Aluminum ion (1+) + Pyridine = (Aluminum ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr45.5 ± 2.5kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Zinc ion (1+) + Pyridine = (Zinc ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr59.0 ± 1.7kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Cobalt ion (1+) + Pyridine = (Cobalt ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr59.0 ± 3.0kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Copper ion (1+) + Pyridine = (Copper ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr58.7 ± 2.5kcal/molCIDTRodgers, Stanley, et al., 2000RCD

Sodium ion (1+) + Pyridine = (Sodium ion (1+) • Pyridine)

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

Quantity Value Units Method Reference Comment
Δr30.3 ± 0.7kcal/molCIDTAmunugama and Rodgers, 2000RCD

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.

Schafman and Wenthold, 2007
Schafman, B.S.; Wenthold, P.G., Regioselectivity of pyridine deprotonation in the gas phase, J. Org. Chem., 2007, 72, 5, 1645-1651, https://doi.org/10.1021/jo062117x . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P., Formation and Reactions of Heteroaromatic Anions in the Gas Phase, J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001 . [all data]

Bruins, Ferrer-Correia, et al., 1978
Bruins, A.P.; Ferrer-Correia, A.J.; Harrison, A.G.; Jennings, K.R.; Mithcum, R.K., Negative ion chemical ionization mass spectrometry of some aromatic compounds using O-. as the reagent ion, Adv. Mass Spectrom., 1978, 7, 355. [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]

Hales and Herington, 1957
Hales, J.L.; Herington, E.F.G., Equilibrium between pyridine and piperidine, Trans. Faraday Soc., 1957, 53, 616-622. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Burrows and King, 1935
Burrows, G.H.; King, L.A., Jr., The free energy change that accompanies hydrogenation of pyridine to piperidine, J. Am. Chem. Soc., 1935, 57, 1789-1791. [all data]

Hiraoka, Mizuse, et al., 1988
Hiraoka, K.; Mizuse, S.; Yamabe, S., Determination of the Stabilities and Structures of X-(C6H6) Clusters (X = Cl, Br, and I), Chem. Phys. Lett., 1988, 147, 2-3, 174, https://doi.org/10.1016/0009-2614(88)85078-4 . [all data]

Amunugama and Rodgers, 2000
Amunugama, R.; Rodgers, M.T., Absolute Alkali Metal Ion Binding Affinities of Several Azines Determined by Threshold Collision-Induced Dissociation and Ab Initio Theory, Int. J. Mass Spectrom., 2000, 195/196, 439, https://doi.org/10.1016/S1387-3806(99)00145-1 . [all data]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P., Binding Energies and Stabilities of Potassium Ion Complexes from Studies of Gas Phase Ion Equilibria K+ + M = K+.M, J. Am. Chem. Soc., 1976, 98, 20, 6133, https://doi.org/10.1021/ja00436a011 . [all data]

Le Barbu, Schiedt, et al., 2002
Le Barbu, K.; Schiedt, J.; Weinkauf, R.; Schlag, E.W.; Nilles, J.M.; Xu, S.J.; Thomas, O.C.; Bowen, K.H., Microsolvation of small anions by aromatic molecules: An exploratory study, J. Chem. Phys., 2002, 116, 22, 9663-9671, https://doi.org/10.1063/1.1475750 . [all data]

Shaofeng and Pilcher, 1988
Shaofeng, L.; Pilcher, G., Enthalpy of formation of pyridine-N-oxide: the dissociation enthalpy of the (N-O) bond, J. Chem. Thermodyn., 1988, 20, 463-465. [all data]

Rodgers, Stanley, et al., 2000
Rodgers, M.T.; Stanley, J.R.; Amunugama, R., Periodic Trends in the Binding of Metal Ions to Pyridine Studied by Threshold Collision-Induced Dissociation and Density Functional Theory, J. Am. Chem. Soc., 2000, 122, 44, 10969, https://doi.org/10.1021/ja0027923 . [all data]


Notes

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