Acetamide, N-phenyl-

• Formula: C₈H₉NO
• Molecular weight: 135.1632
• IUPAC Standard InChI: InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) Copy

  
• IUPAC Standard InChIKey: FZERHIULMFGESH-UHFFFAOYSA-N Copy
• CAS Registry Number: 103-84-4
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Acetanilide; Acetamidobenzene; Acetanil; Acetoanilide; Acetylaniline; Antifebrin; Benzenamine, N-acetyl-; N-Acetylaniline; N-Phenylacetamide; Phenalgene; Phenalgin; Acetylaminobenzene; Acetic acid anilide; Acetanilid; Aniline, N-acetyl-; USAF EK-3; AN [Analgesic]; N-Acetylaminobenzene; NSC 7636
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Constant pressure heat capacity of solid

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

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^- +  =

By formula: C₈H₈NO^- + H⁺ = C₈H₉NO

 +  = C₁₀H₁₁NO₂ + 

By formula: C₈H₉NO + C₂H₄O₂ = C₁₀H₁₁NO₂ + H₂O

 +  =  + 

By formula: C₈H₉NO + H₂O = C₆H₇N + C₂H₄O₂

 +  =  + 

By formula: C₄H₅N₃O + C₆H₇N = C₈H₉NO + C₂H₃N₃

 +  =  + 

By formula: C₃H₄N₄O + C₆H₇N = C₈H₉NO + CH₂N₄

 +  =  + 

By formula: C₄H₆O₃ + C₆H₇N = C₈H₉NO + C₂H₄O₂

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

Appearance energy determinations

De-protonation reactions

C₈H₈NO^- +  =

By formula: C₈H₈NO^- + H⁺ = C₈H₉NO

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (KBr PELLET); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLID (SPLIT MULL); PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution

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

• gas

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

Gas Chromatography

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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

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

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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), 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]

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), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,solid	Constant pressure heat capacity of solid
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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