o-Toluidine

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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
Δfgas53.2 ± 0.5kJ/molCcrSteele, Chirico, et al., 1994see Steele, Chirico, et al., 1990; ALS
Δfgas54.8kJ/molCcbDraeger, 1984ALS
Δfgas51.4kJ/molN/APushin, 1954Value computed using ΔfHliquid° value of -6.5 kj/mol from Pushin, 1954 and ΔvapH° value of 57.9 kj/mol from Steele, Chirico, et al., 1994.; 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
Δfliquid-4.72 ± 0.96kJ/molCcrSteele, Chirico, et al., 1994see Steele, Chirico, et al., 1990; ALS
Δfliquid-6.49kJ/molCcbPushin, 1954Author's hf298_condensed=-4.0 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-4036.09 ± 0.88kJ/molCcrSteele, Chirico, et al., 1994see Steele, Chirico, et al., 1990; ALS
Δcliquid-4034.kJ/molCcbPushin, 1954Author's hf298_condensed=-4.0 kcal/mol; ALS
Δcliquid-4064.0kJ/molCcbSwarts, 1909ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
164.4303.15Guseinov, Mirzaliev, et al., 1988T = 303 to 463 K. p= 0.1 MPa. Unsmoothed experimental datum. Cp(liq) = 0.8056 + 0.0023634T + (0.0017364 - 8.1591x10-6T)P kJ/kg*K (303.15 to 523.15 K, 0.1 to 25 MPa).; DH
209.6302.5de Kolossowsky and Udowenko, 1934DH
209.6302.5Kolosovskii and Udovenko, 1934DH
201.7288.Radulescu and Jula, 1934DH
211.3298.von Reis, 1881T = 294 to 485 K.; DH

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil473. ± 2.KAVGN/AAverage of 16 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus252. ± 8.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple258.730KN/ASteele, Chirico, et al., 1994, 2Uncertainty assigned by TRC = 0.005 K; TRC
Quantity Value Units Method Reference Comment
Tc694.15KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc37.4902barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2.5331 bar; TRC
Quantity Value Units Method Reference Comment
Δvap57. ± 10.kJ/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
57.8300.EB,IPSteele, Chirico, et al., 1994Based on data from 290. to 517. K.; AC
54.5340.EB,IPSteele, Chirico, et al., 1994Based on data from 290. to 517. K.; AC
51.5380.EB,IPSteele, Chirico, et al., 1994Based on data from 290. to 517. K.; AC
48.6420.EB,IPSteele, Chirico, et al., 1994Based on data from 290. to 517. K.; AC
45.7460.EB,IPSteele, Chirico, et al., 1994Based on data from 290. to 517. K.; AC
42.7500.EB.IPSteele, Chirico, et al., 1994Based on data from 290. to 517. K.; AC
50.0406.AStephenson and Malanowski, 1987Based on data from 391. to 474. K. See also Dreisbach and Shrader, 1949 and Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
391.61 to 473.54.191681617.232-87.126Dreisbach and Shrader, 1949Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
8.100249.55Meva'a and Lichanot, 1990DH
11.66287.6Steele, Chirico, et al., 1994AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
32.249.55Meva'a and Lichanot, 1990DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 by: 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

Benzene, isocyanato- + o-Toluidine = Urea, N-(2-methylphenyl)-N'-phenyl-

By formula: C7H5NO + C7H9N = C14H14N2O

Quantity Value Units Method Reference Comment
Δr-93.0kJ/molCmPannone and Macosko, 1987liquid phase

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:
LL - Sharon G. Lias and Joel F. Liebman
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)7.47 ± 0.04eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)890.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity859.1kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.58EISelim, Rabbih, et al., 1992LL
7.45 ± 0.02PEMaier and Turner, 1973LLK
7.52PECowling and Johnstone, 1973LLK
7.44 ± 0.02PIPotapov and Iskakov, 1971LLK
7.6 ± 0.1CTSFarrell and Newton, 1966RDSH
7.7 ± 0.1EIEland, Shepherd, et al., 1966RDSH
7.69CTSKinoshita, 1962RDSH
7.75CTSBriegleb and Czekalla, 1959RDSH
7.84PEPalmer, Moyes, et al., 1979Vertical value; LLK
7.83PEKobayashi and Nagakura, 1974Vertical value; LLK
7.83PEKobayashi and Nagakura, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H6+10.53 ± 0.07?EISelim, Rabbih, et al., 1992LL
C7H8N+11.25 ± 0.05HPIPotapov and Iskakov, 1971LLK

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible 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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible 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

Spectrum

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Mass spectrum
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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1998.
NIST MS number 290511

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Lang (editor), 1973
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 19737
Instrument Unicam SP 800 B
Melting point 200.3

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Steele, Chirico, et al., 1994
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Knipmeyer, S.E., The thermodynamic properties of 2-methylaniline and trans-(r,S)-decahydroquinoline, J. Chem. Thermodyn., 1994, 26, 515-544. [all data]

Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Knipmeyer, S.E., The thermodynamic properties of 2-methylaniline and trans-(R,S)-decahydroquinoline, Topical Rept., work performed under cooperative agreement No. FC22-83FE60149, Bartlesville,OK, (NIPER-459), 1990, 1-52. [all data]

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]

Radulescu and Jula, 1934
Radulescu, D.; Jula, O., Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen, Z. Phys. Chem., 1934, B26, 390-393. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Steele, Chirico, et al., 1994, 2
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Knipmeyer, S.E., The thermodynamic properties of 2-methylaniline and trans-(R,S)-decahydroquinoline, J. Chem. Thermodyn., 1994, 26, 5, 515, https://doi.org/10.1006/jcht.1994.1061 . [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [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]

Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A., Vapor Pressure--Temperature Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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]

Pannone and Macosko, 1987
Pannone, M.C.; Macosko, C.W., Kinetics of isocyanate amine reactions, J. Appl. Polym. Sci., 1987, 34, 2409-2432. [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]

Selim, Rabbih, et al., 1992
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A.; Hawash, M.F., Electron impact study of [C6H6]+ fragment ions produced from isomeric C7H9N precursors using the deconvoluted first differential technique and kinetic release measurements, Int. J. Mass Spectrom. Ion Processes, 1992, 113, 133. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [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]

Potapov and Iskakov, 1971
Potapov, V.K.; Iskakov, L.I., Electronic structure and photoionization of aromatic amines, High Energy Chem., 1971, 5, 237, In original 264. [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]

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [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]

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]

Lang (editor), 1973
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1973, 18, 31. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References