Acetophenone

• Formula: C₈H₈O
• Molecular weight: 120.1485
• IUPAC Standard InChI:
  

  InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 Download the identifier in a file.

• IUPAC Standard InChIKey: KWOLFJPFCHCOCG-UHFFFAOYSA-N
• CAS Registry Number: 98-86-2
• 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.
• Isotopologues:
  • Acetophenone-«alpha»,«alpha»,«alpha»-d3
• Other names: Ethanone, 1-phenyl-; Acetophenon; Benzoyl methide; Hypnon; Hypnone; Methyl phenyl ketone; Phenyl methyl ketone; 1-Phenylethanone; Acetylbenzene; 1-Phenyl-1-ethanone; Ketone, methyl phenyl-; USAF EK-496; Acetofenon; Benzene, acetyl-; Dymex; Rcra waste number U004; Acetylbenzol; NSC 7635; Phenylethanone; 1-phenylethanone (acetophenone)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 4.1
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Gas 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
fH°gas	-20.71 ± 0.40	kcal/mol	N/A	Cox and Pilcher, 1970	Review; Heat of formation from Colomina, Latorre, et al., 1961; ALS
Quantity	Value	Units	Method	Reference	Comment
S°gas	89.120	cal/mol*K	N/A	Stull D.R., 1969	GT

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
fH°liquid	-34.07 ± 0.25	kcal/mol	Ccb	Colomina, Latorre, et al., 1961	Reanalyzed by Cox and Pilcher, 1970, Original value = -34.06 ± 0.25 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
cH°liquid	-989.6	kcal/mol	Ccb	Seno, Tsuchiya, et al., 1975	Corresponding «DELTA»fHºliquid = -36.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
cH°liquid	-991.62 ± 0.21	kcal/mol	Ccb	Colomina, Latorre, et al., 1961	Corresponding «DELTA»fHºliquid = -34.05 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
cH°liquid	-988.5	kcal/mol	Ccb	Guinchant, 1918	Corresponding «DELTA»fHºliquid = -37.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

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, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Tboil	475. ± 1.	K	AVG	N/A	Average of 12 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Tfus	293.0 ± 0.6	K	AVG	N/A	Average of 8 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Tc	713.	K	N/A	Steele, Chirico, et al., 1996	Uncertainty assigned by TRC = 2. K; TRC
Tc	709.6	K	N/A	Teja and Rosenthal, 1991	Uncertainty assigned by TRC = 1. K; TRC
Tc	709.5	K	N/A	Teja and Anselme, 1990	Uncertainty assigned by TRC = 0.6 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Pc	43.42	atm	N/A	Steele, Chirico, et al., 1996	Uncertainty assigned by TRC = 1.48 atm; from extraploation of obs. vapor pressures to Tc; TRC
Pc	39.58	atm	N/A	Teja and Rosenthal, 1991	Uncertainty assigned by TRC = 0.30 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
c	2.62	mol/l	N/A	Steele, Chirico, et al., 1996	Uncertainty assigned by TRC = 0.10 mol/l; TRC
c	2.59	mol/l	N/A	Teja and Anselme, 1990	Uncertainty assigned by TRC = 0.05 mol/l; TRC
Quantity	Value	Units	Method	Reference	Comment
vapH°	13.2 ± 0.1	kcal/mol	EB	Steele, Chirico, et al., 1996, 2	Based on data from 360. - 520. K.; AC
vapH°	12.8	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 343. - 383. K.; AC
vapH°	12.6	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 343. - 383. K.; AC
vapH°	13.8	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 343. - 383. K.; AC
vapH°	13.36 ± 0.30	kcal/mol	V	Cox and Pilcher, 1970	Review; Heat of formation from Colomina, Latorre, et al., 1961; ALS

Reduced pressure boiling point

Enthalpy of vaporization

vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
12.6 ± 0.1	340.	EB	Steele, Chirico, et al., 1996, 2	Based on data from 360. - 520. K.; AC
12.0 ± 0.07	380.	EB	Steele, Chirico, et al., 1996, 2	Based on data from 360. - 520. K.; AC
11.4 ± 0.07	420.	EB	Steele, Chirico, et al., 1996, 2	Based on data from 360. - 520. K.; AC
10.8 ± 0.1	460.	EB	Steele, Chirico, et al., 1996, 2	Based on data from 360. - 520. K.; AC
10.1 ± 0.1	500.	EB	Steele, Chirico, et al., 1996, 2	Based on data from 360. - 520. K.; AC
11.9	390.	A	Stephenson and Malanowski, 1987	Based on data from 375. - 603. K.; AC
10.0	398.	GS,EB	Collerson, Counsell, et al., 1965	Based on data from 383. - 437. K.; AC
12.2	325.	N/A	Stull, 1947	Based on data from 310. - 476. K.; AC

Antoine Equation Parameters

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

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Enthalpy of fusion

fusH (kcal/mol)	Temperature (K)	Reference	Comment
3.979	292.7	Louguinine and Dupont, 1911	See also Sedláková, Malijevská, et al., 2006.; AC

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

 +  = (  )

By formula: Br^- + C₈H₈O = (Br^-  C₈H₈O)

Quantity	Value	Units	Method	Reference	Comment
rH°	14.1 ± 1.8	kcal/mol	IMRE	Paul and Kebarle, 1991	gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity	Value	Units	Method	Reference	Comment
rS°	20.	cal/mol*K	N/A	Paul and Kebarle, 1991	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
rG°	5.6 ± 1.0	kcal/mol	IMRE	Paul and Kebarle, 1991	gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

rG° (kcal/mol)	T (K)	Method	Reference	Comment
5.6	423.	PHPMS	Paul and Kebarle, 1991	gas phase; Entropy change calculated or estimated; M

C₈H₇O^- +  =

By formula: C₈H₇O^- + H⁺ = C₈H₈O

Quantity	Value	Units	Method	Reference	Comment
rH°	361.3 ± 2.1	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
rH°	362.0 ± 2.7	kcal/mol	D-EA	Zimmerman, Reed, et al., 1977	gas phase; B
rH°	362.3 ± 2.6	kcal/mol	G+TS	Cumming and Kebarle, 1978	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
rG°	354.5 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
rG°	355.5 ± 2.0	kcal/mol	IMRE	Cumming and Kebarle, 1978	gas phase; B

C₈H₉O +  = (C₈H₉O  )

By formula: C₈H₉O + C₈H₈O = (C₈H₉O  C₈H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity	Value	Units	Method	Reference	Comment
rH°	26.8	kcal/mol	PHPMS	Meot-Ner (Mautner) and Sieck, 1991	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
rS°	27.2	cal/mol*K	PHPMS	Meot-Ner (Mautner) and Sieck, 1991	gas phase; M

 +  = (  )

By formula: Cl^- + C₈H₈O = (Cl^-  C₈H₈O)

Quantity	Value	Units	Method	Reference	Comment
rG°	9.50	kcal/mol	TDEq	French, Ikuta, et al., 1982	gas phase; B

Free energy of reaction

rG° (kcal/mol)	T (K)	Method	Reference	Comment
7.1	421.	PHPMS	French, Ikuta, et al., 1982	gas phase; M

 +  =  + 

By formula: C₇H₆O + C₈H₈O = H₂O + C₁₅H₁₂O

Quantity	Value	Units	Method	Reference	Comment
rH°	-15.54 ± 0.45	kcal/mol	Cm	Hao, Chang, et al., 1985	liquid phase; solvent: Aqueous NaOH; ALS

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); PERKIN-ELMER 180 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (LESS THAN 10% IN CCl4 FOR 4000-1330 CM^-1, LESS THAN 10% IN CS2 FOR 1330-600 CM^-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• VAPOR (12 MICROLITER AT 150 C); PERKIN-ELMER 180; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2-3 CM^-1 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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Colomina, Latorre, et al., 1961
Colomina, M.; Latorre, C.; Perez-Ossorio, R., Heats of combustion of five alkyl phenyl ketones, Pure & Appl. Chem., 1961, 2, 133-135. [all data]

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Seno, Tsuchiya, et al., 1975
Seno, M.; Tsuchiya, S.; Kise, H.; Asahara, T., Studies on bond character in phosphorus ylides by combustion heat and x-ray photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1975, 48, 2001-2005. [all data]

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [all data]

Phillip, 1939
Phillip, N.M., Adiabatic and isothermal compressibilities of liquids, Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]

Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor pressure of acetophenone, (+-)-1,2-butanediol, (+-)-1,3-butanediol, diethylene glycol monopropyl ether, 1,3-dimethyladamantane, 2-ethoxyethyl acetate, ethyl octyl sufide, and pentyl acetate, J. Chem. Eng. Data, 1996, 41, 1255-68. [all data]

Teja and Rosenthal, 1991
Teja, A.S.; Rosenthal, D.J., The critical pressures and temperatures of ten substances using a low residence time flow apparatus in Experimental Results for Phase Equilibria and Pure Component Properties, DIPPR DATA Series No. 1, 1991. [all data]

Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J., The critical properties of thermally stable and unstable fluids. I. 1985 results, AIChE Symp. Ser., 1990, 86, 279, 115-21. [all data]

Steele, Chirico, et al., 1996, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure of Acetophenone, (±)-1,2-Butanediol, (±)-1,3-Butanediol, Diethylene Glycol Monopropyl Ether, 1,3-Dimethyladamantane, 2-Ethoxyethyl Acetate, Ethyl Octyl Sulfide, and Pentyl Acetate, J. Chem. Eng. Data, 1996, 41, 6, 1255-1268, https://doi.org/10.1021/je9601117 . [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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]

Collerson, Counsell, et al., 1965
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S., 677. Thermodynamic properties of organic oxygen compounds. Part XV. Purification and vapour pressures of some ketones and ethers, J. Chem. Soc., 1965, 3697, https://doi.org/10.1039/jr9650003697 . [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]

Louguinine and Dupont, 1911
Louguinine, W.; Dupont, G., Bull. Soc. Chim. Fr., 1911, 9, 219. [all data]

Sedláková, Malijevská, et al., 2006
Sedláková, Zuzana; Malijevská, Ivona; Rehák, Karel; Vrbka, Pavel, Solid-Liquid and Liquid-Liquid Equilibrium in the Formamide-Acetophenone System, Collect. Czech. Chem. Commun., 2006, 71, 9, 1350-1358, https://doi.org/10.1135/cccc20061350 . [all data]

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]

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]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [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]

Meot-Ner (Mautner) and Sieck, 1991
Meot-Ner (Mautner), M.; Sieck, L.W., Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range, J. Am. Chem. Soc., 1991, 113, 12, 4448, https://doi.org/10.1021/ja00012a012 . [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Hao, Chang, et al., 1985
Hao, J.; Chang, J.; Wang, K.; Liu, Y.; Zhong, G., Heat of reaction of chalcone by calorimetric measurement, Huaxue Tongbao, 1985, 15-16. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°gas	Entropy of gas at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  cH°liquid	Enthalpy of combustion of liquid at standard conditions
  fH°gas	Enthalpy of formation of gas at standard conditions
  fH°liquid	Enthalpy of formation of liquid at standard conditions
  fusH	Enthalpy of fusion
  rG°	Free energy of reaction at standard conditions
  rH°	Enthalpy of reaction at standard conditions
  rS°	Entropy of reaction at standard conditions
  vapH	Enthalpy of vaporization
  vapH°	Enthalpy of vaporization at standard conditions
  c	Critical density

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