Pyridine, 3-methyl-
- Formula: C6H7N
- Molecular weight: 93.1265
- IUPAC Standard InChI: InChI=1S/C6H7N/c1-6-3-2-4-7-5-6/h2-5H,1H3
- IUPAC Standard InChIKey: ITQTTZVARXURQS-UHFFFAOYSA-N
- CAS Registry Number: 108-99-6
- 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: 3-Picoline; β-Methylpyridine; β-Picoline; m-Picoline; 3-Methylpyridine; meta-Methylpyridine; beta-Picoline; 5-Methylpyridine; m-Methylpyridine; NSC 18251
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 24.76 ± 0.31 | kcal/mol | Ccb | Gerasimov, Gubareva, et al., 1992 | %hf298_condensed[kJ/mol]=-61.1±1.3; ALS |
| ΔfH°gas | 25.37 ± 0.17 | kcal/mol | Ccb | Scott, Good, et al., 1963 | ALS |
| ΔfH°gas | 27.14 ± 0.24 | kcal/mol | Cm | Andon, Cox, et al., 1957 | ALS |
| ΔfH°gas | 27.16 ± 0.24 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
| ΔfH°gas | 18.0 | kcal/mol | N/A | Constam and White, 1903 | Value computed using ΔfHliquid° value of 33.0 kj/mol from Constam and White, 1903 and ΔvapH° value of 42.5 kj/mol from Gerasimov, Gubareva, et al., 1992.; DRB |
Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | 14.6 ± 0.31 | kcal/mol | Ccb | Gerasimov, Gubareva, et al., 1992 | %hf298_condensed[kJ/mol]=-61.1±1.3; ALS |
| ΔfH°liquid | 14.75 ± 0.14 | kcal/mol | Ccb | Scott, Good, et al., 1963 | ALS |
| ΔfH°liquid | 16.32 ± 0.24 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
| ΔfH°liquid | 7.8 | kcal/mol | Ccb | Constam and White, 1903 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -788.81 ± 0.31 | kcal/mol | Ccb | Gerasimov, Gubareva, et al., 1992 | %hf298_condensed[kJ/mol]=-61.1±1.3; ALS |
| ΔcH°liquid | -818.17 ± 0.12 | kcal/mol | Ccb | Scott, Good, et al., 1963 | ALS |
| ΔcH°liquid | -819.74 ± 0.24 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
| ΔcH°liquid | -813.1 | kcal/mol | Ccb | Constam and White, 1903 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 51.699 | cal/mol*K | N/A | Scott, Good, et al., 1963 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 37.928 | 298.15 | Scott, Good, et al., 1963 | T = 12 to 400 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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° | 377.8 ± 3.1 | kcal/mol | G+TS | DePuy, Kass, et al., 1988 | gas phase; Acid: 3-methylpyridine. Comparable to EtOH.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 371.0 ± 3.0 | kcal/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Acid: 3-methylpyridine. Comparable to EtOH.; B |
+
= (
•
)
By formula: Li+ + C6H7N = (Li+ • C6H7N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 47.0 ± 3.5 | kcal/mol | CIDT | Rodgers, 2001 | RCD |
+
= (
•
)
By formula: Na+ + C6H7N = (Na+ • C6H7N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 31.8 ± 1.0 | kcal/mol | CIDT | Rodgers, 2001 | RCD |
+
= (
•
)
By formula: K+ + C6H7N = (K+ • C6H7N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 23.8 ± 0.8 | kcal/mol | CIDT | Rodgers, 2001 | RCD |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Gerasimov, Gubareva, et al., 1992
Gerasimov, P.A.; Gubareva, A.I.; Tarbeeva, N.A.; Kunderenko, V.M.,
Physicochemical characteristics of β-picoline,
J. Appl. Chem. USSR, 1992, 65, 388-390. [all data]
Scott, Good, et al., 1963
Scott, D.W.; Good, W.D.; Guthrie, G.B.; Todd, S.S.; Hossenlopp, I.A.; Osborn, A.G.; McCullough, J.P.,
Chemical thermodynamic properties and internal rotation of methylpyridines. II. 3-methylpyridine,
J. Phys. Chem., 1963, 67, 685-689. [all data]
Andon, Cox, et al., 1957
Andon, R.J.L.; Cox, J.D.; Herington, E.F.G.; Martin, J.F.,
The second virial coefficients of pyridine and benzene, and certain of their methyl homologues,
Trans. Faraday Soc., 1957, 53, 1074. [all data]
Cox, Challoner, et al., 1954
Cox, J.D.; Challoner, A.R.; Meetham, A.R.,
The heats of combustion of pyridine and certain of its derivatives,
J. Chem. Soc., 1954, 265-271. [all data]
Constam and White, 1903
Constam, E.J.; White, J.,
Physico-chemical investigations in the pyridine series,
Am. Chem. J., 1903, 29, 1-49. [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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