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Aniline

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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
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 bullet Aniline)

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

Quantity Value Units Method Reference Comment
Deltar14.6 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar6.1 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.1423.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
Deltar368.18 ± 0.30kcal/molD-EAWren, Vogelhuber, et al., 2012gas phase; B
Deltar366.4 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar360.91 ± 0.67kcal/molH-TSWren, Vogelhuber, et al., 2012gas phase; B
Deltar359.1 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C9H13N+ + Aniline = (C9H13N+ bullet Aniline)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar13.3kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar(26.)cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
5.9283.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C7H9N+ + Aniline = (C7H9N+ bullet Aniline)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar16.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar9.0kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C8H11N+ + Aniline = (C8H11N+ bullet Aniline)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar14.2kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar6.5kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Fluorine anion + Aniline = (Fluorine anion bullet Aniline)

By formula: F- + C6H7N = (F- bullet C6H7N)

Quantity Value Units Method Reference Comment
Deltar31.2 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar26.2cal/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
Deltar23.4 ± 2.0kcal/molIMRELarson and McMahon, 1983gas phase; B,M

C6H7N+ + Aniline = (C6H7N+ bullet Aniline)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar17.5kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar24.6cal/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
Deltar-12.8kcal/molKinKalnin'sh, 1988liquid phase; solvent: Acetonitrile; ALS
Deltar-13.0kcal/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
Deltar-0.8kcal/molEqkMatvienko, Kachurin, et al., 1982liquid phase; Methansulfonic acid; ALS
Deltar-0.9kcal/molKinKachurin, Matvienko, et al., 1979liquid phase; ALS

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

By formula: K+ + C6H7N = (K+ bullet C6H7N)

Quantity Value Units Method Reference Comment
Deltar22.8kcal/molHPMSDavidson and Kebarle, 1976gas phase; M
Quantity Value Units Method Reference Comment
Deltar23.7cal/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
Deltar-39.7 ± 0.5kcal/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
Deltar-38.6 ± 0.2kcal/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
Deltar-35.6 ± 0.2kcal/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
Deltar-10.05 ± 0.06kcal/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
Deltar-20.0 ± 0.07kcal/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
Deltar-23.5 ± 0.26kcal/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
Deltar27.1 ± 0.5kcal/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
Deltar-19.7 ± 0.48kcal/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
Deltar43.4 ± 1.0kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

Iodide + Aniline = (Iodide bullet Aniline)

By formula: I- + C6H7N = (I- bullet C6H7N)

Quantity Value Units Method Reference Comment
Deltar12.9 ± 1.0kcal/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
Deltar-17.28 ± 0.08kcal/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
Deltar-20.22 ± 0.08kcal/molCmWadso, 1962solid phase; ALS

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

By formula: C4H6O3 + C6H7N = C8H9NO + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-24.11 ± 0.06kcal/molCmWadso, 1962liquid phase; ALS

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

By formula: C7H5NO + C6H7N = C13H12N2O

Quantity Value Units Method Reference Comment
Deltar-21.3 ± 1.2kcal/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

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