Benzenamine, N,N,4-trimethyl-
- Formula: C9H13N
- Molecular weight: 135.2062
- IUPAC Standard InChIKey: GYVGXEWAOAAJEU-UHFFFAOYSA-N
- CAS Registry Number: 99-97-8
- 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, N,N-dimethyl-; p-Methyl-N,N-dimethylaniline; p,N,N-trimethylaniline; Dimethyl-p-toluidine; N,N-Dimethyl-p-toluidine; N,N-Dimethyl-p-tolylamine; N,N-Dimethyl-4-methylaniline; N,N,4-Trimethylbenzenamine; N,N-Dimethyl-4-toluidine; N,N,4-Trimethylaniline; Dimetil-p-toluidina; Benzeneamine,N,N,4-trimethyl-; 1-(Dimethylamino)-4-methylbenzene; NSC 1785; p-(Dimethylamino)toluene
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 68.9 ± 7.4 | kJ/mol | Ccb | Riberio da Silva, Riberio da Silva, et al., 1996 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 11.7 ± 2.7 | kJ/mol | Ccb | Riberio da Silva, Riberio da Silva, et al., 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5411.2 ± 2.4 | kJ/mol | Ccb | Riberio da Silva, Riberio da Silva, et al., 1996 |
Phase change data
Go To: Top, Gas phase thermochemistry data, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 484.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 483.15 | K | N/A | Broxton, Deady, et al., 1970 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 484.3 | K | N/A | Perkin, 1896 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 57.2 ± 6.9 | kJ/mol | V | Riberio da Silva, Riberio da Silva, et al., 1996 | ALS |
ΔvapH° | 57.2 | kJ/mol | N/A | Riberio da Silva, Riberio da Silva, et al., 1996 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
60.7 | 338. | A | Stephenson and Malanowski, 1987 | Based on data from 323. to 483. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
323.3 to 482.7 | 3.71671 | 1364.255 | -116.036 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
By formula: C9H13N+ + C9H13N = (C9H13N+ • C9H13N)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.7 | kJ/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | (110.) | J/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
34. | 331. | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
C9H12N- + =
By formula: C9H12N- + H+ = C9H13N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1614. ± 21. | kJ/mol | G+TS | Caldwell and Bartmess | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1586. ± 21. | kJ/mol | IMRB | Caldwell and Bartmess | gas phase; B |
By formula: C10H10Fe+ + C9H13N = (C10H10Fe+ • C9H13N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 51.0 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1989 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 86.2 | J/mol*K | PHPMS | Meot-Ner (Mautner), 1989 | gas phase; M |
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, Phase change 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.
Riberio da Silva, Riberio da Silva, et al., 1996
Riberio da Silva, M.A.V.; Riberio da Silva, M.D.M.C.; Monteiro, M.F.B.M.; Gomes, M.L.A.C.N.; Chickos, J.S.; Smith, A.P.; Liebman, J.F.,
Thermochemical studies for determination of the molar enthalpy of formation of aniline derivatives,
Struct. Chem., 1996, 7, 367-373. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Broxton, Deady, et al., 1970
Broxton, T.J.; Deady, L.W.; Katritzky, A.R.; Liu, A.; Topsom, R.D.,
Infrared Intensities as a Quantitative Measure of Intermolecular Inter- actions XII. π-Distortions in teh Ground States of Some p-Alkylbenzenes,
J. Am. Chem. Soc., 1970, 92, 6845. [all data]
Perkin, 1896
Perkin, W.H.,
LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds,
J. Chem. Soc., 1896, 69, 1025-1257. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S.,
Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems,
J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026
. [all data]
Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E.,
, Unpublished results. [all data]
Meot-Ner (Mautner), 1989
Meot-Ner (Mautner), M.,
Ion DChemistry of Ferrocene. Thermochemistry of Ionization and Protonation and Solvent Clustering. Slow and Entropy - Driven Proton - Transfer Kinetics,
J. Am. Chem. Soc., 1989, 111, 8, 2830, https://doi.org/10.1021/ja00190a014
. [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, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature Tboil Boiling point 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 ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.