Pyridine
- Formula: C5H5N
- Molecular weight: 79.0999
- IUPAC Standard InChIKey: JUJWROOIHBZHMG-UHFFFAOYSA-N
- CAS Registry Number: 110-86-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Isotopologues:
- Other names: Azabenzene; Azine; NCI-C55301; Piridina; Pirydyna; Pyridin; Rcra waste number U196; UN 1282; Pyr; CP 32; NSC 406123
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Ion clustering 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
B - John E. Bartmess
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
By formula: (Ag+ • 2C5H5N) + C5H5N = (Ag+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 69.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 117. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Ag+ • 3C5H5N) + C5H5N = (Ag+ • 4C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 74.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 169. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: Al+ + C5H5N = (Al+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 190. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: C5H6N+ + C5H5N = (C5H6N+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 105. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 103. | kJ/mol | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrH° | 110. | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrH° | 99.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrH° | 99.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 124. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 118. | J/mol*K | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrS° | 134. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
By formula: (C5H6N+ • C5H5N) + C5H5N = (C5H6N+ • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.7 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 124. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (C5H6N+ • 2C5H5N) + C5H5N = (C5H6N+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 56.9 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 159. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
By formula: Cl- + C5H5N = (Cl- • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 53.1 ± 8.4 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 82.4 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 28. ± 11. | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B |
By formula: (Cl- • C5H5N) + C5H5N = (Cl- • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 49.0 | kJ/mol | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 94.6 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
By formula: Co+ + C5H5N = (Co+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 247. ± 13. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cr+ + C5H5N = (Cr+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 197. ± 12. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cu+ + C5H5N = (Cu+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 246. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Fe+ + C5H5N = (Fe+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 223. ± 9.2 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: H2O3- + C5H5N + H2O = C5H7NO3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 137. ± 9.6 | kJ/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: K+ + C5H5N = (K+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 90. ± 4. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 86.6 | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 77.8 | J/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: Li+ + C5H5N = (Li+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 181. ± 15. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 180. | kJ/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: Mg+ + C5H5N = (Mg+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 200. ± 6.7 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mn+ + C5H5N = (Mn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 182. ± 8.8 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
+
= C5H5N2O-
By formula: NO- + C5H5N = C5H5N2O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 56.9 ± 9.6 | kJ/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: Na+ + C5H5N = (Na+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 127. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
By formula: Ni+ + C5H5N = (Ni+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 255. ± 15. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
+
= C5H5NO2-
By formula: O2- + C5H5N = C5H5NO2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 90.8 ± 9.6 | kJ/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: Sc+ + C5H5N = (Sc+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 231. ± 10. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ti+ + C5H5N = (Ti+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 217. ± 9.6 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: V+ + C5H5N = (V+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 218. ± 13. | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Zn+ + C5H5N = (Zn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 247. ± 7.1 | kJ/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
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.
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]
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]
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]
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]
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]
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]
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]
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]
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]
Notes
Go To: Top, Ion clustering data, References
- Symbols used in this document:
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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