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
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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
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 9.99 | kcal/mol | Ccb | Draeger, 1984 | ALS |
| ΔfH°gas | 14.9 | kcal/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 |
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° | 367.3 ± 2.1 | kcal/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° | 360.1 ± 2.0 | kcal/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° | -40.2 ± 0.4 | kcal/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° | -40.7 ± 0.2 | kcal/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° | -39.3 ± 0.3 | kcal/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° | 34.9 ± 0.2 | kcal/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° | -0.3 | kcal/mol | Kin | Kachurin, Matvienko, et al., 1980 | liquid phase; ALS |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | SE-30 | 180. | 1092. | Oszczapowicz, Osek, et al., 1985 | N2, Chromosorb A AW; Column length: 3. m |
| Packed | SE-30 | 180. | 1092. | Oszczapowicz, Osek, et al., 1984 | N2, Chromosorb W AW; Column length: 3. m |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Carbowax 20M | 165. | 1828.9 | Ellis and Still, 1979 | Chromosorb W, AW-DMCS |
| Packed | PEG-2000 | 179. | 1822. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
| Packed | PEG-2000 | 200. | 1825. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
| Packed | PEG-2000 | 200. | 1839. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
| Packed | PEG-20M | 210. | 1833.9 | Still, Evans, et al., 1972 | Chromosorb G; Column length: 3. m |
| Packed | PEG-20M | 210. | 1836.1 | Still, Evans, et al., 1972 | Chromosorb G; Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-1 | 1042.1 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
| Packed | SE-30 | 1068. | Peng, Ding, et al., 1988 | He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m |
| Capillary | DB-5 | 1073. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | 5 % Phenyl methyl siloxane | 1068. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-30 | 1056.5 | Bur'yan and Nabivach, 1992 | 1.7 K/min; Tstart: 82. C; Tend: 177. C |
| Capillary | Ultra-1 | 1037. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1822. | Peng, Yang, et al., 1991 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 176.89 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, 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]
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]
Oszczapowicz, Osek, et al., 1985
Oszczapowicz, J.; Osek, J.; Ciszkowski, K.; Krawczyk, W.; Ostrowski, M.,
Retention Indices of Dimethylbenzamidines and Benzylideneamines on a Non-Polar Column,
J. Chromatogr., 1985, 330, 79-85, https://doi.org/10.1016/S0021-9673(01)81964-6
. [all data]
Oszczapowicz, Osek, et al., 1984
Oszczapowicz, J.; Osek, J.; Dolecka, E.,
Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar column,
J. Chromatogr., 1984, 315, 95-100, https://doi.org/10.1016/S0021-9673(01)90727-7
. [all data]
Ellis and Still, 1979
Ellis, T.S.; Still, R.H.,
Thermal degradation of polymers. XXIII. Vacuum pyrolysis of poly(p-N,N-dimethylaminostyrene); the products volatile at pyrolysis temperature, liquid or gaseous at room temperature,
J. Appl. Polym. Sci., 1979, 23, 10, 2871-2880, https://doi.org/10.1002/app.1979.070231004
. [all data]
Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L.,
Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases,
Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]
Still, Evans, et al., 1972
Still, R.H.; Evans, M.B.; Whitehead, A.,
Thermal Degradation of Polymers. V. Vacuum Pyrolysis of Poly (p-N,N-dimethylaminostyrene) . The Products Volatile at Pyrolysis Temperature, Liquid or Gaseous at Room Temperature,
J. Appl. Polym. Sci., 1972, 16, 12, 3207-3221, https://doi.org/10.1002/app.1972.070161213
. [all data]
Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P.,
Use of incremental models to estimate the retention indexes of aromatic compounds,
Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946
. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603
. [all data]
Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y.,
Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry,
J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2
. [all data]
Bur'yan and Nabivach, 1992
Bur'yan, P.; Nabivach, V.M.,
Investigation of composition of higher heterocnitrogen bases of brown coal tar,
Coke Chem. (Engl. Transl.), 1992, 5, 29-33. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas 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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