Benzenamine, 3-methyl-
- Formula: C7H9N
- Molecular weight: 107.1531
- IUPAC Standard InChI: InChI=1S/C7H9N/c1-6-3-2-4-7(8)5-6/h2-5H,8H2,1H3
- IUPAC Standard InChIKey: JJYPMNFTHPTTDI-UHFFFAOYSA-N
- CAS Registry Number: 108-44-1
- 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. - Other names: m-Toluidine; m-Aminotoluene; m-Methylaniline; m-Methylbenzenamine; 1-Amino-3-methylbenzene; 3-Aminophenylmethane; 3-Aminotoluene; 3-Methylaniline; 3-Methylbenzenamine; 3-Toluidine; 3-Amino-1-methylbenzene; m-Toluidin; m-Tolylamine; Aniline, 3-methyl-; 3-Aminotoluen; 3-methyl-benzamine; NSC 15349
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics 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 | 61.1 | kJ/mol | Ccb | Draeger, 1984 | ALS |
| ΔfH°gas | 87.9 | kJ/mol | N/A | Pushin, 1954 | Value computed using ΔfHliquid° value of 42.3 kj/mol from Pushin, 1954 and ΔvapH° value of 45.61 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 | 42.3 | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=8.5 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -4083. | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=8.5 kcal/mol; ALS |
| ΔcH°liquid | -4047. | kJ/mol | Ccb | Swarts, 1909 | ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 167.2 | 303.15 | Guseinov, Mirzaliev, et al., 1988 | T = 303 to 463 K. p = 0.1 MPa. Unsmooethed experimental datum. Cp(liq) = 0.8666 + 0.0022600 + (0.0007010 - 6.0538x10-6T)P kJ/kg*K (303.15 to 523.25 K, 0.1 to 25 MPa).; DH |
| 216.7 | 302.7 | de Kolossowsky and Udowenko, 1934 | DH |
| 216.7 | 302.7 | Kolosovskii and Udovenko, 1934 | 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° | 1535. ± 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° | 1505. ± 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: C15H16N2O = C7H9N + C8H7NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 126.2 ± 1.7 | kJ/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase; Dissociation; ALS |
Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C7H9N+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 7.54 ± 0.03 | eV | N/A | N/A | L |
| Quantity | Value | Units | Method | Reference | Comment |
| Proton affinity (review) | 895.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 864.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.55 | PE | Cowling and Johnstone, 1973 | LLK |
| 7.7 ± 0.1 | CTS | Farrell and Newton, 1966 | RDSH |
| 7.6 ± 0.1 | EI | Eland, Shepherd, et al., 1966 | RDSH |
| 7.75 | CTS | Briegleb and Czekalla, 1959 | RDSH |
| 7.50 ± 0.02 | PI | Vilesov and Terenin, 1957 | RDSH |
| 7.82 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
| 7.66 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
| 7.66 | PE | Kobayashi and Nagakura, 1972 | Vertical value; LLK |
De-protonation reactions
C7H8N- + =
By formula: C7H8N- + H+ = C7H9N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1535. ± 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° | 1505. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics 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]
Guseinov, Mirzaliev, et al., 1988
Guseinov, S.O.; Mirzaliev, A.A.; Shakhmuradov, Sh.G.,
Investigation of the isobaric heat capacity of meta- and ortho-toluidine over a wide interval ov varying temperature and pressure, Iaz. Vyssh. Ucheb. Zaved.,
Neft i Gaz 31(9), 1988, 13, 35. [all data]
de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W.,
Determination des chaleurs specifiques des liquides,
Compt. rend., 1934, 198, 1394-1395. [all data]
Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W.,
Specific heat of liquids. II.,
Zhur. Obshchei Khim., 1934, 4, 1027-1033. [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]
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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Cowling and Johnstone, 1973
Cowling, S.A.; Johnstone, R.A.W.,
Photoelectron spectroscopy: The effects of steric inhibition to resonance in anilines,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 161. [all data]
Farrell and Newton, 1966
Farrell, P.G.; Newton, J.,
Ionization potentials of primary aromatic amines and aza-hydrocarbons,
Tetrahedron Lett., 1966, 5517. [all data]
Eland, Shepherd, et al., 1966
Eland, J.H.D.; Shepherd, P.J.; Danby, C.J.,
Ionization potentials of aromatic molecules determined by analytical interpretation of electron impact data,
Z. Naturforsch., 1966, 21a, 1580. [all data]
Briegleb and Czekalla, 1959
Briegleb, G.; Czekalla, J.,
Die Bestimmung von lonisierungsenergien aus den Spektren von Elektronenubergangskomplexen,
Z.Elektrochem., 1959, 63, 6. [all data]
Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N.,
The photoionization of the vapors of certain organic compounds,
Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]
Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Spiers, M.; Ridyard, J.N.A.,
The electronic structure of substituted benzenes; a study of aniline, the toluidines, phenylenediamines and fluoroanilines by photoelectron spectroscopy and ab initio calculations,
J. Mol. Struct., 1979, 53, 235. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Kobayashi and Nagakura, 1972
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of anilines,
Chem. Lett., 1972, 1013. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy 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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