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-209.5 ± 1.5kJ/molCcrSato-Toshima, Kamagughi, et al., 1983Author was aware that data differs from previously reported values; ALS
Δfsolid-209.4 ± 1.0kJ/molCcbJohnson, 1975ALS
Quantity Value Units Method Reference Comment
Δcsolid-4224.8 ± 1.0kJ/molCcrSato-Toshima, Kamagughi, et al., 1983Author was aware that data differs from previously reported values; ALS
Δcsolid-4224.88 ± 0.93kJ/molCcbJohnson, 1975ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
179.3298.15Nilsson and Wadso, 1986DH
191.6323.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 (kJ/mol) Temperature (K) Method Reference Comment
64.8488.AStephenson and Malanowski, 1987Based on data from 473. to 577. K.; AC
66.3402.N/AStull, 1947Based on data from 387. to 577. K.; 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
387. to 576.95.372842920.325-32.916Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
80.6313.5AStephenson and Malanowski, 1987Based on data from 303. to 324. K. See also Aihara, 1955.; AC
87.2326.5AStephenson and Malanowski, 1987Based on data from 317. to 336. K. See also Aihara, 1960.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Method Reference Comment
21.4386.9DSCChen, Tang, et al., 2005AC
18.3387.2N/AVecchio, Catalani, et al., 2004AC
21.67387.5N/ADomalski and Hearing, 1996AC

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
21.653387.525crystaline, IliquidAndon and Connett, 1980, 2DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
55.87387.525crystaline, 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:


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
Δr1454. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Δr1476. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr1425. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B
Δr1447. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

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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Additional Data

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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

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References

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

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]

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]


Notes

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