Aniline

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.


Reaction thermochemistry data

Go To: Top, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

Bromine anion + Aniline = (Bromine anion • Aniline)

By formula: Br- + C6H7N = (Br- • C6H7N)

Quantity Value Units Method Reference Comment
Δr61.1 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 423 K, ΔSaff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Δr84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr26. ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 423 K, ΔSaff taken as that of PhNO2..Br-; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
26.423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

C6H6N- + Hydrogen cation = Aniline

By formula: C6H6N- + H+ = C6H7N

Quantity Value Units Method Reference Comment
Δr1540.5 ± 1.3kJ/molD-EAWren, Vogelhuber, et al., 2012gas phase; B
Δr1533. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1510.0 ± 2.8kJ/molH-TSWren, Vogelhuber, et al., 2012gas phase; B
Δr1502. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C9H13N+ + Aniline = (C9H13N+ • Aniline)

By formula: C9H13N+ + C6H7N = (C9H13N+ • C6H7N)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr55.6kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr(110.)J/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
25.283.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C7H9N+ + Aniline = (C7H9N+ • Aniline)

By formula: C7H9N+ + C6H7N = (C7H9N+ • C6H7N)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr69.9kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr38.kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C8H11N+ + Aniline = (C8H11N+ • Aniline)

By formula: C8H11N+ + C6H7N = (C8H11N+ • C6H7N)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr59.4kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr27.kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Fluorine anion + Aniline = (Fluorine anion • Aniline)

By formula: F- + C6H7N = (F- • C6H7N)

Quantity Value Units Method Reference Comment
Δr131. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; B,M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Δr97.9 ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; B,M

C6H7N+ + Aniline = (C6H7N+ • Aniline)

By formula: C6H7N+ + C6H7N = (C6H7N+ • C6H7N)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr73.2kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr103.J/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

Aniline + Phthalic anhydride = Benzoic acid, 2-[(phenylamino)carbonyl]-

By formula: C6H7N + C8H4O3 = C14H11NO3

Quantity Value Units Method Reference Comment
Δr-53.5kJ/molKinKalnin'sh, 1988liquid phase; solvent: Acetonitrile; ALS
Δr-54.4kJ/molKinPravednikov, Kardash, et al., 1973solid phase; solvent: Tetrahydrofuran; ALS

Aniline, N-methyl- = 0.5Benzenamine, N,N-dimethyl- + 0.5Aniline

By formula: C7H9N = 0.5C8H11N + 0.5C6H7N

Quantity Value Units Method Reference Comment
Δr-3.kJ/molEqkMatvienko, Kachurin, et al., 1982liquid phase; Methansulfonic acid; ALS
Δr-4.kJ/molKinKachurin, Matvienko, et al., 1979liquid phase; ALS

Potassium ion (1+) + Aniline = (Potassium ion (1+) • Aniline)

By formula: K+ + C6H7N = (K+ • C6H7N)

Quantity Value Units Method Reference Comment
Δr95.4kJ/molHPMSDavidson and Kebarle, 1976gas phase; M
Quantity Value Units Method Reference Comment
Δr99.2J/mol*KHPMSDavidson and Kebarle, 1976gas phase; M

Benzoyl iodide + Aniline = Hydrogen iodide + Benzamide, N-phenyl-

By formula: C7H5IO + C6H7N = HI + C13H11NO

Quantity Value Units Method Reference Comment
Δr-166. ± 2.kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene; ALS

Benzoyl bromide + Aniline = Hydrogen bromide + Benzamide, N-phenyl-

By formula: C7H5BrO + C6H7N = HBr + C13H11NO

Quantity Value Units Method Reference Comment
Δr-162. ± 0.8kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene; ALS

Aniline + Benzoyl chloride = Hydrogen chloride + Benzamide, N-phenyl-

By formula: C6H7N + C7H5ClO = HCl + C13H11NO

Quantity Value Units Method Reference Comment
Δr-149. ± 0.8kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene; ALS

Acetamide, N-phenyl- + Water = Aniline + Acetic acid

By formula: C8H9NO + H2O = C6H7N + C2H4O2

Quantity Value Units Method Reference Comment
Δr-42.0 ± 0.3kJ/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

Benzene, 1-isocyanato-4-nitro- + Aniline = N-(4-Nitrophenyl)-N'-phenyl-urea

By formula: C7H4N2O3 + C6H7N = C13H11N3O3

Quantity Value Units Method Reference Comment
Δr-83.8 ± 0.3kJ/molCmKiselev, Malkov, et al., 1989liquid phase; solvent: Dioxane; #TDE; ALS

Cyclohexane, isocyanato- + Aniline = Urea, N-cyclohexyl-N'-phenyl-

By formula: C7H11NO + C6H7N = C13H18N2O

Quantity Value Units Method Reference Comment
Δr-98.4 ± 1.1kJ/molCmKiselev, Malkov, et al., 1989liquid phase; solvent: Dioxane; ALS

2-Propanol, 1-phenoxy-3-(phenylamino)- = Oxirane, (phenoxymethyl)- + Aniline

By formula: C15H17NO2 = C9H10O2 + C6H7N

Quantity Value Units Method Reference Comment
Δr113. ± 2.kJ/molCmKuznetsova, Rakova, et al., 1975solid phase; solvent: DMF; ALS

Benzene, isocyanato- + Aniline = Urea, N,N-diphenyl-

By formula: C7H5NO + C6H7N = C13H12N2O

Quantity Value Units Method Reference Comment
Δr-82.5 ± 2.0kJ/molCmKiselev, Malkov, et al., 1989liquid phase; solvent: Dioxane; ALS

Urea, N,N'-diphenyl- = Benzene, isocyanato- + Aniline

By formula: C13H12N2O = C7H5NO + C6H7N

Quantity Value Units Method Reference Comment
Δr181.7 ± 4.2kJ/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

Iodide + Aniline = (Iodide • Aniline)

By formula: I- + C6H7N = (I- • C6H7N)

Quantity Value Units Method Reference Comment
Δr54.0 ± 4.2kJ/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

1-[1,2,4]Triazol-1-ylethanone + Aniline = Acetamide, N-phenyl- + 1H-1,2,4-Triazole

By formula: C4H5N3O + C6H7N = C8H9NO + C2H3N3

Quantity Value Units Method Reference Comment
Δr-72.3 ± 0.3kJ/molCmWadso, 1962solid phase; ALS

1-Acetyl-1H-tetrazole + Aniline = Acetamide, N-phenyl- + 1H-Tetrazole

By formula: C3H4N4O + C6H7N = C8H9NO + CH2N4

Quantity Value Units Method Reference Comment
Δr-84.6 ± 0.3kJ/molCmWadso, 1962solid phase; ALS

Acetic anhydride + Aniline = Acetamide, N-phenyl- + Acetic acid

By formula: C4H6O3 + C6H7N = C8H9NO + C2H4O2

Quantity Value Units Method Reference Comment
Δr-100.9 ± 0.3kJ/molCmWadso, 1962liquid phase; ALS

Benzene, isocyanato- + Aniline = Urea, N,N'-diphenyl-

By formula: C7H5NO + C6H7N = C13H12N2O

Quantity Value Units Method Reference Comment
Δr-89.1 ± 5.1kJ/molCmPannone and Macosko, 1987liquid phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Wren, Vogelhuber, et al., 2012
Wren, S.W.; Vogelhuber, K.M.; Ichino, T.; Stanton, J.F.; Lineberger, W.C., Photoelectron Spectroscopy of Anilinide and Acidity of Aniline, J. Phys. Chem. A, 2012, 116, 12, 3118-3123, https://doi.org/10.1021/jp211463r . [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]

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]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

Kalnin'sh, 1988
Kalnin'sh, K.K., Autocatalysis and effects of the solvent in the reaction of phthalic anhydride with aniline derivatives, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 1768-1773. [all data]

Pravednikov, Kardash, et al., 1973
Pravednikov, A.N.; Kardash, I.Ye.; Glukhoyedov, N.P.; Ardashnikov, A.Ya., Some features of the synthesis of heat-resistant heterocyclic polymers, Polym. Sci. USSR, 1973, 15, 399-410. [all data]

Matvienko, Kachurin, et al., 1982
Matvienko, N.M.; Kachurin, O.I.; Chekhuta, V.G., Kinetics and equilibrium of the transalkylation reaction of N-methylarylamines, Russ. Chem. Rev., 1982, 48, 42-45. [all data]

Kachurin, Matvienko, et al., 1979
Kachurin, O.I.; Matvienko, N.M.; Chekhuta, V.G., Disproportionation of N-methylaniline, Russ. Chem. Rev., 1979, 45, 43-47. [all data]

Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P., Binding Energies and Stabilities of Potassium Ion Complexes from Studies of Gas Phase Ion Equilibria K+ + M = K+.M, J. Am. Chem. Soc., 1976, 98, 20, 6133, https://doi.org/10.1021/ja00436a011 . [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]

Wadso, 1965
Wadso, I., Thermochemical properties of diacetimide, N-butyldiacetimide and N-phenyldiacetimide, Acta Chem. Scand., 1965, 19, 1079-1087. [all data]

Kiselev, Malkov, et al., 1989
Kiselev, V.D.; Malkov, V.B.; Murzin, D.G.; Shakirov, I.M.; Konovalov, A.I., Thermochemical study of the reaction of isocyanate with amines, Dokl. Phys. Chem. (Engl. Transl.), 1989, 308, 711-713, In original 111. [all data]

Kuznetsova, Rakova, et al., 1975
Kuznetsova, V.P.; Rakova, G.V.; Miroshnichenko, E.A.; Lebedev, Yu.A.; Enikolopyan, N.S., Thermochemical study of the interaction of epoxy compounds with primary amines, Dokl. Phys. Chem. (Engl. Transl.), 1975, 225, 1231-1234. [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]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]

Wadso, 1962
Wadso, I., Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride, Acta Chem. Scand., 1962, 16, 471-478. [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]


Notes

Go To: Top, Reaction thermochemistry data, References