Acetic acid, phenyl ester
- Formula: C8H8O2
- Molecular weight: 136.1479
- IUPAC Standard InChIKey: IPBVNPXQWQGGJP-UHFFFAOYSA-N
- CAS Registry Number: 122-79-2
- 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. - Other names: Phenol acetate; Phenyl acetate; Fenylester kyseliny octove; Phenyl ester of acetic acid
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -326. ± 0.8 | kJ/mol | Ccb | Lebedeva and Katin, 1972 | |
ΔfH°liquid | -334.8 ± 0.92 | kJ/mol | Cm | Wadso, 1960 | Heat of formation derived by Cox and Pilcher, 1970 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3966.0 ± 0.84 | kJ/mol | Ccb | Lebedeva and Katin, 1972 | Corresponding ΔfHºliquid = -325.4 kJ/mol (simple calculation by NIST; no Washburn corrections) |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 469. ± 1. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 53. ± 6. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
51.7 | 326. | A | Stephenson and Malanowski, 1987 | Based on data from 311. to 469. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
311.4 to 469.1 | 5.02585 | 2174.699 | -36.045 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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:
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: C3H9Si+ + C8H8O2 = (C3H9Si+ • C8H8O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 204. | kJ/mol | PHPMS | Wojtyniak and Stone, 1986 | gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 133. | J/mol*K | N/A | Wojtyniak and Stone, 1986 | gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
141. | 468. | PHPMS | Wojtyniak and Stone, 1986 | gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M |
By formula: C8H8O2 + H2O = C6H6O + C2H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.7 ± 0.2 | kJ/mol | Cm | Wadso, 1960 | liquid phase; Heat of hydrolysis; 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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C8H8O2+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference |
---|---|---|
8.6 ± 0.05 | PE | Bouchoux, 1978 |
8.8 ± 0.2 | EI | Gamble, Gilbert, et al., 1971 |
8.75 ± 0.03 | EI | Benezra and Bursey, 1971 |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O+ | 12.8 ± 0.2 | cyclo-C6H5 | EI | Gamble, Gilbert, et al., 1971 | |
C2H3O+ | 12.83 ± 0.03 | C6H5O | EI | Benezra and Bursey, 1971 | |
C6H6O+ | 9.9 ± 0.2 | CH2=C=O | EI | Gamble, Gilbert, et al., 1971 | |
C6H6O+ | 9.57 ± 0.03 | CH2=C=O | EI | Benezra and Bursey, 1971 |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
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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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 | Chuck Anderson, Aldrich Chemical Co. |
NIST MS number | 107257 |
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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 160. | 1008. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.32 mm |
Capillary | SE-30 | 180. | 1025. | Tarjan, Nyiredy, et al., 1989 | |
Capillary | OV-101 | 160. | 1008. | Haken and Korhonen, 1983 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | OV-101 | 180. | 1025. | Haken and Korhonen, 1983 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | OV-101 | 200. | 1033. | Haken and Korhonen, 1983 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-351 | 160. | 1633. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.32 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | ZB-1 | 1033. | Urbanczyk, Staniewski, et al., 2002 | 30. m/0.25 mm/0.50 μm, He, 50. C @ 3. min, 10. K/min, 280. C @ 10. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 1068. | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Packed | SE-30 | 1050. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1065. | Geldon, 1989 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1660. | Peng, Yang, et al., 1991 | Program: 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), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lebedeva and Katin, 1972
Lebedeva, N.D.; Katin, Yu.A.,
Heats of combustion of certain monosubstituted benzenes,
Russ. J. Phys. Chem. (Engl. Transl.), 1972, 46, 1088. [all data]
Wadso, 1960
Wadso, I.,
Heats of hydrolysis of phenyl acetate and phenyl thiolacetate,
Acta Chem. Scand., 1960, 14, 561-565. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J.,
A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases,
Can. J. Chem., 1986, 74, 59. [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]
Gamble, Gilbert, et al., 1971
Gamble, A.A.; Gilbert, J.R.; Tillett, J.G.,
Substituent effects on the mass spectra of substituted phenyl acetates,
Org. Mass Spectrom., 1971, 5, 1093. [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]
Evans and Haken, 1989
Evans, M.B.; Haken, J.K.,
Dispersion and selectivity indices in gas chromatography. IV. Chlorinated aromatic compounds,
J. Chromatogr., 1989, 468, 373-382, https://doi.org/10.1016/S0021-9673(00)96332-5
. [all data]
Tarjan, Nyiredy, et al., 1989
Tarjan, G.; Nyiredy, Sz.; Gyor, M.; Lombosi, E.R.; Lombosi, T.S.; Budahegyi, M.V.; Meszaros, S.Y.; Takacs, J.M.,
Review. Thirtieth Anniversary of the Retention Index According to Kovats in Gas-Liquid Chromatography,
J. Chromatogr., 1989, 472, 1-92, https://doi.org/10.1016/S0021-9673(00)94099-8
. [all data]
Haken and Korhonen, 1983
Haken, J.K.; Korhonen, I.O.O.,
Gas chromatography of homologous esters. XXI. Capillary column studies of the chlorinated phenyl acetates,
J. Chromatogr., 1983, 257, 267-273, https://doi.org/10.1016/S0021-9673(01)88182-6
. [all data]
Urbanczyk, Staniewski, et al., 2002
Urbanczyk, A.; Staniewski, J.; Szymanowski, J.,
Abraham model in gas chromatography of phenol pollutants,
Anal. Chim. Acta., 2002, 466, 1, 151-159, https://doi.org/10.1016/S0003-2670(02)00544-5
. [all data]
Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Geldon, 1989
Geldon, A.L.,
Ground Water Hydrology of the Central Raton Basin, Colorado and New Mexico, US Geological Survey, US Government Printing Office, 1989, 104. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [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 T Temperature Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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