p-Aminotoluene
- Formula: C7H9N
- Molecular weight: 107.1531
- IUPAC Standard InChI: InChI=1S/C7H9N/c1-6-2-4-7(8)5-3-6/h2-5H,8H2,1H3
- IUPAC Standard InChIKey: RZXMPPFPUUCRFN-UHFFFAOYSA-N
- CAS Registry Number: 106-49-0
- 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: p-Toluidine; p-Methylaniline; p-Methylbenzenamine; p-Tolylamine; C.I. Azoic coupling component 107; 1-Amino-4-methylbenzene; 4-Aminotoluene; 4-Methylaniline; 4-Methylbenzenamine; 4-Toluidine; Benzenamine, 4-methyl-; 4-Amino-1-methylbenzene; 4-Tolylamine; p-Toluidin; Aniline, p-methyl-; 4-Aminotoluen; Rcra waste number U353; C.I. 37107; Naphtol AS-KG; Naphtol AS-KGLL; NSC 15350
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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 | 41.8 | kJ/mol | Ccb | Draeger, 1984 | ALS |
| ΔfH°gas | 62.2 | kJ/mol | N/A | Pushin, 1954 | Value computed using ΔfHliquid° value of 19 kj/mol from Pushin, 1954 and ΔvapH° value of 43.18 kj/mol from missing citation.; 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 | 19. | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=1.8 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -4059. | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=1.8 kcal/mol; ALS |
| ΔcH°liquid | -4061.4 | kJ/mol | Ccb | Swarts, 1909 | ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 165.2 | 298.15 | Meva'a and Lichanot, 1990 | T = 273 to 368 K. Cp(c) = 147.505 + 0.604T + 3.525x10-3T2 + 2.351x10-5T3 J/mol*K (-100 to 30 C). Cp(liq) = 212.982 + 0.182T J/mol*K (50 to 95 C).; DH |
| 124.3 | 293. | Campbell and Campbell, 1940 | DH |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
C7H8N- + =
By formula: C7H8N- + H+ = C7H9N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1537. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1507. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
+
=
+
By formula: C7H9N + C7H5IO = HI + C14H13NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -168. ± 2. | kJ/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid phase; solvent: Benzene; ALS |
+
=
+
By formula: C7H9N + C7H5BrO = HBr + C14H13NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -170. ± 0.8 | kJ/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid phase; solvent: Benzene; ALS |
+
=
+
By formula: C7H9N + C7H5ClO = C14H13NO + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -164. ± 1. | kJ/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid phase; solvent: Benzene; ALS |
C15H16N2O = +
By formula: C15H16N2O = C7H9N + C8H7NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 146.1 ± 0.9 | kJ/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase; Dissociation; ALS |
= 0.5
+ 0.5
By formula: C8H11N = 0.5C7H9N + 0.5C9H13N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1. | kJ/mol | Kin | Kachurin, Matvienko, et al., 1980 | liquid phase; ALS |
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.
Draeger, 1984
Draeger, J.A.,
Chemical-thermodynamic properties of molecules that undergo inversion. II. The methylanilines,
J. Chem. Thermodyn., 1984, 16, 1067-1073. [all data]
Pushin, 1954
Pushin, N.A.,
Heats of combustion and heats of formation of isomeric organic compounds,
Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]
Swarts, 1909
Swarts, M.F.,
Sur la chaleur de formation de l'aniline et de quelquesuns de ses derives,
Recl. Trav. Chim. Pays-Bas, 1909, 28, 155-165. [all data]
Meva'a and Lichanot, 1990
Meva'a, L.M.; Lichanot, A.,
Proprietes thermodynamiques en phase condensee des ortho, meta et para fluorotoluene, cresol et toluidine,
Thermochim. Acta, 1990, 158, 335-345. [all data]
Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R.,
The heats of solution, heats of formation,
specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Kiselev, Khuzyasheva, et al., 1979
Kiselev, V.D.; Khuzyasheva, d.G.; Konovalov, A.I.,
Thermochemical study of the acylation of para-substituted anilines,
J. Gen. Chem. USSR, 1979, 49, 2273-2276. [all data]
Chimishkyan, Svetlova, et al., 1984
Chimishkyan, A.L.; Svetlova, L.P.; Leonova, T.V.; Gluyaev, N.D.,
Thermal decomposition of substituted ureas,
J. Gen. Chem. USSR, 1984, 54, 1317-1320. [all data]
Kachurin, Matvienko, et al., 1980
Kachurin, O.I.; Matvienko, N.M.; Chekhuta, V.G.,
N-Methylated p-toluidines,
Russ. Chem. Rev., 1980, 46, 64-67. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid 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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