Pyridine, 4-methyl-
- Formula: C6H7N
- Molecular weight: 93.1265
- IUPAC Standard InChI: InChI=1S/C6H7N/c1-6-2-4-7-5-3-6/h2-5H,1H3
- IUPAC Standard InChIKey: FKNQCJSGGFJEIZ-UHFFFAOYSA-N
- CAS Registry Number: 108-89-4
- 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. - Other names: 4-Picoline; γ-Methylpyridine; γ-Picoline; p-Methylpyridine; p-Picoline; Ba 35846; 4-Methylpyridine; para-Methylpyridine; gamma-Picoline; NSC 18252
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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 as indicated in comments:
B - John E. Bartmess
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
C6H6N- + =
By formula: C6H6N- + H+ = C6H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 369.7 ± 5.1 | kcal/mol | G+TS | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
| ΔrH° | 374.8 ± 3.1 | kcal/mol | G+TS | DePuy, Kass, et al., 1988 | gas phase; Acid: p-methylpyridine. Between iPrOH, MeCN.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 362.9 ± 5.0 | kcal/mol | IMRB | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
| ΔrG° | 368.0 ± 3.0 | kcal/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Acid: p-methylpyridine. Between iPrOH, MeCN.; B |
+
= (
•
)
By formula: Li+ + C6H7N = (Li+ • C6H7N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 46.9 ± 3.3 | kcal/mol | CIDT | Rodgers, 2001 | RCD |
+
= (
•
)
By formula: Na+ + C6H7N = (Na+ • C6H7N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 31.9 ± 0.9 | kcal/mol | CIDT | Rodgers, 2001 | RCD |
+
= (
•
)
By formula: K+ + C6H7N = (K+ • C6H7N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 23.6 ± 1.0 | kcal/mol | CIDT | Rodgers, 2001 | RCD |
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 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]
Rodgers, 2001
Rodgers, M.T.,
Substituent Effects in the Binding of Alkali Metal Ions to Pyridines, Studied by Threshold Collision-Induced Dissociation and ab Initio Theory: The Methylpyridines,
J. Phys. Chem. A, 2001, 105, 11, 2374, https://doi.org/10.1021/jp004055z
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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