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acetyl fluoride

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-106.4 ± 0.5kcal/molCmPritchard and Skinner, 1950Heat of formation derived by Cox and Pilcher, 1970, see Carson and Skinner, 1949 and Pritchard and Skinner, 1950, 2
Deltafgas-104.6kcal/molCmCarson and Skinner, 1949 

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
Deltafliquid-111.47 ± 0.02kcal/molCmPritchard and Skinner, 1950, 2Corrected for CODATA value of «DELTA»fH; HF(100)
Deltafliquid-112.4 ± 0.1kcal/molCmPritchard and Skinner, 1950Heat of formation derived by Cox and Pilcher, 1970, see Carson and Skinner, 1949 and Pritchard and Skinner, 1950, 2
Deltafliquid-110.6 ± 0.7kcal/molCmCarson and Skinner, 1949 

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

Quantity Value Units Method Reference Comment
Tboil293.KN/APCR Inc., 1990BS
Tboil294.0KN/AWeast and Grasselli, 1989BS
Tboil293. - 294.KN/ABuckingham and Donaghy, 1982BS
Tboil295.KN/AYamase, 1961Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Deltavap6.0 ± 0.5kcal/molEPritchard and Skinner, 1950Heat of formation derived by Cox and Pilcher, 1970, see Carson and Skinner, 1949 and Pritchard and Skinner, 1950, 2; ALS
Deltavap6.kcal/molECarson and Skinner, 1949ALS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
3.42266.AStephenson and Malanowski, 1987Based on data from 195. - 281. K.; AC

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

C2H2FO- + Hydrogen cation = acetyl fluoride

By formula: C2H2FO- + H+ = C2H3FO

Quantity Value Units Method Reference Comment
Deltar355.9 ± 3.8kcal/molG+TSFarid and McMahon, 1980gas phase; Between MeCOCH2F, cyclopentadiene; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar349.0 ± 3.7kcal/molIMRBFarid and McMahon, 1980gas phase; Between MeCOCH2F, cyclopentadiene; value altered from reference due to change in acidity scale; B

2Sodium hydroxide + acetyl fluoride = Acetic acid, sodium salt + sodium fluoride + Water

By formula: 2HNaO + C2H3FO = C2H3NaO2 + FNa + H2O

Quantity Value Units Method Reference Comment
Deltar-13.42 ± 0.02kcal/molCmPritchard and Skinner, 1950, 2liquid phase; Corrected for CODATA value of «DELTA»fH; HF(100); ALS
Deltar-42.4kcal/molCmCarson and Skinner, 1949liquid 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
11.51 ± 0.02PEChadwick and Katrib, 1974LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+12.3FEIMajer, Patrick, et al., 1961RDSH

De-protonation reactions

C2H2FO- + Hydrogen cation = acetyl fluoride

By formula: C2H2FO- + H+ = C2H3FO

Quantity Value Units Method Reference Comment
Deltar355.9 ± 3.8kcal/molG+TSFarid and McMahon, 1980gas phase; Between MeCOCH2F, cyclopentadiene; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar349.0 ± 3.7kcal/molIMRBFarid and McMahon, 1980gas phase; Between MeCOCH2F, cyclopentadiene; value altered from reference due to change in acidity scale; B

Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   Cs     Symmetry Number sigma = 1


 Sym.   No   Approximate   Selected Freq.  Infrared   Raman   Comments 
 Species   type of mode   Value   Rating   Value  Phase  Value  Phase

a' 1 CH3 d-str 3043  C 3043 W gas 3043 VW liq.
a' 2 CH3 s-str 2955  C 2955 VW gas 2952 S liq.
a' 3 C=O str 1870  C 1870 VS gas 1847 S liq.
a' 4 CH3 d-deform 1440  C 1440 W gas 1440 W liq.
a' 5 CH3 s-deform 1378  C 1378 M gas 1379 W liq.
a' 6 CF str 1188  C 1188 VS gas 1178 VW liq.
a' 7 CH3 rock 1000  C 1000 M gas 1003 M liq.
a' 8 CC str 826  C 826 S gas 822 S liq.
a' 9 OCF deform 598  C 598 W gas 602 M liq.
a' 10 OCF deform 420  D 420 VW gas 428 W liq.
a 11 CH3 d-str 3004  C 3004 W gas 3004 VW liq.
a 12 CH3 d-deform 1437  D 1437 W gas 1440 W liq.
a 13 CH3 rock 1054  C 1054 M gas
a 14 C=O op-bend 567  C 567 W gas 573 W liq.
a 15 CH3 torsion 123  E CF

Source: Shimanouchi, 1972

Notes

VSVery strong
SStrong
MMedium
WWeak
VWVery weak
CFCalculated frequency
C3~6 cm-1 uncertainty
D6~15 cm-1 uncertainty
E15~30 cm-1 uncertainty

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, NIST Free Links, Notes

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

Pritchard and Skinner, 1950
Pritchard, H.O.; Skinner, H.A., The heats of hydrolysis of the chloro-substituted acetyl chlorides, J. Chem. Soc., 1950, 272-276. [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]

Carson and Skinner, 1949
Carson, A.S.; Skinner, H.A., 201. Carbon-halogen bond energies in the acetyl halides, J. Chem. Soc., 1949, 936-939. [all data]

Pritchard and Skinner, 1950, 2
Pritchard, H.O.; Skinner, H.A., The heat of hydrolysis of acetyl fluoride, J. Chem. Soc., 1950, 1099. [all data]

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [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]

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

Yamase, 1961
Yamase, Y., Friedel-Crafts Acylation II. Relative Reactivity for Some Acyl Halides, Bull. Chem. Soc. Jpn., 1961, 34, 480-84. [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]

Farid and McMahon, 1980
Farid, R.; McMahon, T.B., The gas phase acidities of fluorinated acetones. An ICR investigation of the role of fluorine substituents in the stabilization of planar carbanions, Can. J. Chem., 1980, 58, 2307. [all data]

Chadwick and Katrib, 1974
Chadwick, D.; Katrib, A., Photoelectron spectra of acetaldehyde and acetyl halides, J. Electron Spectrosc. Relat. Phenom., 1974, 3, 39. [all data]

Majer, Patrick, et al., 1961
Majer, J.R.; Patrick, C.R.; Robb, J.C., Appearance potentials of the acetyl radical-ion, J. Chem. Soc. Faraday Trans., 1961, 57, 14. [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume II, J. Phys. Chem. Ref. Data, 1972, 6, 3, 993-1102. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, NIST Free Links, References