Acetamide, N-phenyl-

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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
Δfsolid-50.07 ± 0.36kcal/molCcrSato-Toshima, Kamagughi, et al., 1983Author was aware that data differs from previously reported values; ALS
Δfsolid-50.06 ± 0.24kcal/molCcbJohnson, 1975ALS
Quantity Value Units Method Reference Comment
Δcsolid-1009.8 ± 0.24kcal/molCcrSato-Toshima, Kamagughi, et al., 1983Author was aware that data differs from previously reported values; ALS
Δcsolid-1009.77 ± 0.22kcal/molCcbJohnson, 1975ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
42.85298.15Nilsson and Wadso, 1986DH
45.79323.Satoh and Sogabe, 1941T = 0 to 100 C. Mean value.; 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil577.2KN/AWeast and Grasselli, 1989BS
Tboil578.15KN/APerkin, 1896Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Tfus388. ± 2.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple387.520KN/AAndon and Connett, 1980Uncertainty assigned by TRC = 0.01 K; TRC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
15.5488.AStephenson and Malanowski, 1987Based on data from 473. to 577. K.; AC
15.8402.N/AStull, 1947Based on data from 387. to 577. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
387. to 576.95.367132920.325-32.916Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
19.3313.5AStephenson and Malanowski, 1987Based on data from 303. to 324. K. See also Aihara, 1955.; AC
20.8326.5AStephenson and Malanowski, 1987Based on data from 317. to 336. K. See also Aihara, 1960.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
5.11386.9DSCChen, Tang, et al., 2005AC
4.37387.2N/AVecchio, Catalani, et al., 2004AC
5.179387.5N/ADomalski and Hearing, 1996AC

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
5.1752387.525crystaline, IliquidAndon and Connett, 1980, 2DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
13.35387.525crystaline, IliquidAndon and Connett, 1980, 2DH

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 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

C8H8NO- + Hydrogen cation = Acetamide, N-phenyl-

By formula: C8H8NO- + H+ = C8H9NO

Quantity Value Units Method Reference Comment
Δr347.5 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr352.8 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr340.6 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr345.8 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

Acetamide, N-phenyl- + Acetic acid = C10H11NO2 + Water

By formula: C8H9NO + C2H4O2 = C10H11NO2 + H2O

Quantity Value Units Method Reference Comment
Δr10.88 ± 0.07kcal/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

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

By formula: C8H9NO + H2O = C6H7N + C2H4O2

Quantity Value Units Method Reference Comment
Δr-10.05 ± 0.06kcal/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

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-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
Δr-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
Δr-24.11 ± 0.06kcal/molCmWadso, 1962liquid phase; 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 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

Ionization energy determinations

IE (eV) Method Reference Comment
8.30 ± 0.10PEBouchoux, 1978LLK
8.60EIBaldwin, Loudon, et al., 1976LLK
8.18 ± 0.03EIBenezra and Bursey, 1971LLK
8.39 ± 0.10EICotter, 1964RDSH
8.46PENakagaki, Kobayashi, et al., 1980Vertical value; LLK
8.46 ± 0.05PESzepes, Distefano, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+13.22 ± 0.03?EIBenezra and Bursey, 1971LLK
C6H7N+10.60?EIBaldwin, Loudon, et al., 1976LLK
C6H7N+10.45 ± 0.03CH2=C=OEIBenezra and Bursey, 1971LLK
C6H7N+8.88 ± 0.15?EICotter, 1964RDSH
C8H8NO+11.00HEIBaldwin, Loudon, et al., 1976LLK

De-protonation reactions

C8H8NO- + Hydrogen cation = Acetamide, N-phenyl-

By formula: C8H8NO- + H+ = C8H9NO

Quantity Value Units Method Reference Comment
Δr347.5 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr352.8 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr340.6 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr345.8 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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: 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 D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY
NIST MS number 63771

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

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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: 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 Johnson, 1966
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. 19783
Instrument Unicam SP 500
Melting point 115-115.6

Gas Chromatography

Go To: Top, 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, 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

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes1362.Zenkevich and Chupalov, 1996Program: not specified
CapillaryPolydimethyl siloxanes1362.Schutz and Wollrab A., 1988Program: not specified
OtherMethyl Silicone1358.Ardrey and Moffat, 1981Program: not specified

References

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

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

Sato-Toshima, Kamagughi, et al., 1983
Sato-Toshima, T.; Kamagughi, A.; Nishiyama, K.; Sakiyama, M.; Seki, S., Enthalpies of combustion of organic compounds. IV. Acetaneilide and nicotinic acid, Bull. Chem. Soc. Jpn., 1983, 56, 51-54. [all data]

Johnson, 1975
Johnson, W.H., The enthalpies of combustion and formation of acetanilide and urea, J. Res. NBS, 1975, 79, 487-491. [all data]

Nilsson and Wadso, 1986
Nilsson, S.-O.; Wadso, I., A flow-microcalorimetric vessel for solution of slightly soluble solids, J. Chem. Thermodynam., 1986, 18, 1125-1133. [all data]

Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T., The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (1), Sci., Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 197-203. [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]

Perkin, 1896
Perkin, W.H., LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds, J. Chem. Soc., 1896, 69, 1025-1257. [all data]

Andon and Connett, 1980
Andon, R.J.L.; Connett, J.E., Calibrants for thermal analysis. measurement of their enthalpies of fusion by adiabatic calorimetry., Thermochim. Acta, 1980, 42, 241. [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]

Aihara, 1955
Aihara, A., J. Chem. Soc. Jpn. Pure Chem. Sect., 1955, 76, 492. [all data]

Aihara, 1960
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. III. Amides, Bull. Chem. Soc. Jpn., 1960, 33, 9, 1188-1194, https://doi.org/10.1246/bcsj.33.1188 . [all data]

Chen, Tang, et al., 2005
Chen, Yan-Ping; Tang, Muoi; Kuo, Ju-Chia, Solid--liquid equilibria for binary mixtures of N-phenylacetamide with 4-aminoacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone, Fluid Phase Equilibria, 2005, 232, 1-2, 182-188, https://doi.org/10.1016/j.fluid.2005.03.023 . [all data]

Vecchio, Catalani, et al., 2004
Vecchio, Stefano; Catalani, Alessia; Rossi, Vanessa; Tomassetti, Mauro, Thermal analysis study on vaporization of some analgesics. Acetanilide and derivatives, Thermochimica Acta, 2004, 420, 1-2, 99-104, https://doi.org/10.1016/j.tca.2003.09.039 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Andon and Connett, 1980, 2
Andon, R.J.L.; Connett, J.E., Calibrants for thermal analysis. Measurement of their enthalpies of fusion by adiabatic calorimetry, Thermochim. Acta, 1980, 42, 241-247. [all data]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

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

Bouchoux, 1978
Bouchoux, G., Ionisation et fragmentation en spectrometrie de masse VIII. Energies d'activation de deux fragmentations competitives, dissociation de l'acetate de phenyle et de l'acetanilide sous impact electronique, Int. J. Mass Spectrom. Ion Phys., 1978, 26, 379. [all data]

Baldwin, Loudon, et al., 1976
Baldwin, M.A.; Loudon, A.G.; Maccoll, A.; Webb, K.S., The nature and fragmentation pathways of the molecular ions of some arylureas, arylthioureas, acetanilides, thioacetanilides and related compounds, Org. Mass Spectrom., 1976, 11, 1181. [all data]

Benezra and Bursey, 1971
Benezra, S.A.; Bursey, M.M., ortho-Effects on ordering factors in mass spectral rearrangements. Loss of keten from halogenated phenyl acetates and acetanilides, J. Chem. Soc. B, 1971, 1515. [all data]

Cotter, 1964
Cotter, J.L., Electron impact fragmentation patterns of acetanilide and benzamide, J. Chem. Soc., 1964, 5477. [all data]

Nakagaki, Kobayashi, et al., 1980
Nakagaki, R.; Kobayashi, T.; Nagakura, S., Conformations of acetanilide and related compounds studied by ultraviolet photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1980, 53, 901. [all data]

Szepes, Distefano, et al., 1974
Szepes, L.; Distefano, G.; Pignataro, S., Steric inhibition of resonance in acetanilides by UV photoelectron spectroscopy, Ann. Chim., 1974, 64, 159. [all data]

Johnson, 1966
Johnson, E.A., UV atlas of organic compaunds, 1966, 2, D6/5. [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Schutz and Wollrab A., 1988
Schutz, H.; Wollrab A., The significance of the retention index in toxicologic analysis II, Pharmazie in unzerer Zeit, 1988, 17, 4, 97-101. [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]


Notes

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