Acetophenone

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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
Δfgas-86.7 ± 1.7kJ/molN/ACox and Pilcher, 1970Review; Heat of formation from Colomina, Latorre, et al., 1961; ALS
Quantity Value Units Method Reference Comment
gas372.88J/mol*KN/AStull D.R., 1969GT

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C8H8O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.28 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)861.1kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity829.3kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.3339 ± 0.0043ECDWentworth, Kao, et al., 1975B
0.3340 ± 0.0040ECDWentworth and Chen, 1967B
2.550 ± 0.030LPESYagi, Maeyama, et al., 2007This vertical detachment energy value seems at least 2 eV too large. - JEB; B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
863.5 ± 0.5Tabrizchi and Shooshtari, 2003T = 413-467K; Authors report only relative PAs. Absolute values are referenced here to PA(CH3COOC2H5) = 835.7 kJ/mol as listed in Hunter and Lias, 1998, although average PA(CH3COOC2H5) from the literature sources in Hunter and Lias, 1998 is 831.0 kJ/mol; MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.1 ± 0.1EIDallinga, Nibbering, et al., 1981LLK
9.28PIMcLoughlin and Traeger, 1979LLK
9.45EIElder, Beynon, et al., 1976LLK
9.1 ± 0.1PEEgdell, Green, et al., 1975LLK
9.1EIMcLafferty, Bente, et al., 1973LLK
9.50EIBenoit, 1973LLK
9.3 ± 0.2PIIskakov and Potapov, 1971LLK
9.15 ± 0.03EIBock, Alt, et al., 1969RDSH
9.27 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
9.6PITerenin, 1961RDSH
9.38PEDistefano, Granozzi, et al., 1987Vertical value; LBLHLM
9.51PEGal, Geribaldi, et al., 1985Vertical value; LBLHLM
9.51PEPfister-Guillouzo, Geribaldi, et al., 1982Vertical value; LBLHLM
9.45PECentineo, Fragala, et al., 1978Vertical value; LLK
9.45PEKoenig, Wielesek, et al., 1977Vertical value; LLK
9.35PEBenoit and Harrison, 1977Vertical value; LLK
8.9PERao, 1975Vertical value; LLK
9.37PEKobayashi and Nagakura, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+11.40 ± 0.28?EIFoffani, Pignataro, et al., 1963RDSH
C6H5+13.97CO+CH3EIBenoit, 1973LLK
C6H5+13.28CO+CH3EIJohnstone and Mellon, 1972LLK
C6H5+13.42 ± 0.07?EIFoffani, Pignataro, et al., 1963RDSH
C7H5O+9.67CH3PIMcLoughlin and Traeger, 1979LLK
C7H5O+10.50 ± 0.01CH3EIHelal and Zahran, 1978LLK
C7H5O+10.08CH3EIElder, Beynon, et al., 1976LLK
C7H5O+9.6CH3EIMcLafferty, Bente, et al., 1973LLK
C7H5O+10.38CH3EIBenoit, 1973LLK
C7H5O+9.91CH3EIBuchs, Rossetti, et al., 1964RDSH

De-protonation reactions

C8H7O- + Hydrogen cation = Acetophenone

By formula: C8H7O- + H+ = C8H8O

Quantity Value Units Method Reference Comment
Δr1512. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1515. ± 11.kJ/molD-EAZimmerman, Reed, et al., 1977gas phase; B
Δr1516. ± 11.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr1483. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1487. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

Ion clustering 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Bromine anion + Acetophenone = (Bromine anion • Acetophenone)

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

Quantity Value Units Method Reference Comment
Δr59.0 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Δr84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr23. ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
23.423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Chlorine anion + Acetophenone = (Chlorine anion • Acetophenone)

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

Quantity Value Units Method Reference Comment
Δr39.7kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
30.421.PHPMSFrench, Ikuta, et al., 1982gas phase; M

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes

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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Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Chemical Concepts
NIST MS number 223435

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References

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering 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.

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Wentworth, Kao, et al., 1975
Wentworth, W.E.; Kao, L.W.; Becker, R.S., Electron affinities of substituted aromatic compounds, J. Phys. Chem., 1975, 79, 1161. [all data]

Wentworth and Chen, 1967
Wentworth, W.E.; Chen, E., Experimental Determination of the Electron Affinity of Several Aromatic Aldehydes and Ketones, J. Phys. Chem., 1967, 71, 6, 1929, https://doi.org/10.1021/j100865a063 . [all data]

Yagi, Maeyama, et al., 2007
Yagi, I.; Maeyama, T.; Fujii, A.; Mikami, N., Stepwise solvatochromism of ketyl anions in the gas phase: Photodetachment excitation spectroscopy of benzophenone and acetophenone radical anions microsolvated with methanol, J. Phys. Chem. A, 2007, 111, 31, 7646-7652, https://doi.org/10.1021/jp072167l . [all data]

Tabrizchi and Shooshtari, 2003
Tabrizchi, M.; Shooshtari, S., Proton affinity measurements using ion mobility spectrometry, J. Chem. Thermodynamics, 2003, 35, 863. [all data]

Dallinga, Nibbering, et al., 1981
Dallinga, J.W.; Nibbering, N.M.M.; Louter, G.J., Formation and structure of [C8H8O]+ ions, generated from gas phase ions of phenylcyclopropylcarbinol and 1-phenyl-1-(hydroxymethyl)cyclopropane, Org. Mass Spectrom., 1981, 16, 4. [all data]

McLoughlin and Traeger, 1979
McLoughlin, R.G.; Traeger, J.C., A photoionization study of some benzoyl compounds - thermochemistry of [C7H5O]+ formation, Org. Mass Spectrom., 1979, 14, 434. [all data]

Elder, Beynon, et al., 1976
Elder, J.F.; Beynon, J.H.; Cooks, R.G., The benzoyl ion. Thermochemistry and kinetic energy release, Org. Mass Spectrom., 1976, 11, 415. [all data]

Egdell, Green, et al., 1975
Egdell, R.; Green, J.C.; Rao, C.N.R., Photoelectron spectra of substituted benzenes, Chem. Phys. Lett., 1975, 33, 600. [all data]

McLafferty, Bente, et al., 1973
McLafferty, F.W.; Bente, P.F., III; Kornfeld, R.; Tsai, S.-C.; Howe, I., Collisional activation spectra of organic ions, J. Am. Chem. Soc., 1973, 95, 2120. [all data]

Benoit, 1973
Benoit, F., The benzoyl cation: The participation of isolated electronic excited states in the dissociation of molecular ions of the form [C6H5COX]+, Org. Mass Spectrom., 1973, 7, 1407. [all data]

Iskakov and Potapov, 1971
Iskakov, L.I.; Potapov, V.K., Photionization and decomposition of benzaldehyde, acetophenone, and benzophenone, High Energy Chem., 1971, 5, 238, In original 265. [all data]

Bock, Alt, et al., 1969
Bock, H.; Alt, H.; Seidl, H., d-Orbital effects in silicon-substituted π-electron systems. XV. The color of silyl ketones, J. Am. Chem. Soc., 1969, 91, 355. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Terenin, 1961
Terenin, A., Charge transfer in organic solids, induced by light, Proc. Chem. Soc., London, 1961, 321. [all data]

Distefano, Granozzi, et al., 1987
Distefano, G.; Granozzi, G.; Olivato, P.R.; Guerrero, S.A., Hyperconjugative interactions in halogen-substituted carbonyls: Ultraviolet photoelectron spectroscopy of w-halogenoacetophenones, J. Chem. Soc. Perkin Trans. 2, 1987, 1459. [all data]

Gal, Geribaldi, et al., 1985
Gal, J.-F.; Geribaldi, S.; Pfister-Guillouzo, G.; Morris, D.G., Basicity of the carbonyl group. Part 12. Correlations between ionization potentials and lewis basicities in aromatic carbonyl compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 103. [all data]

Pfister-Guillouzo, Geribaldi, et al., 1982
Pfister-Guillouzo, G.; Geribaldi, S.; Gal, J.-F., Spectres photoelectroniques de cyclohexene-2-ones-1 diversement substituees en position 3. Correlations avec la reactivite, Can. J. Chem., 1982, 60, 1163. [all data]

Centineo, Fragala, et al., 1978
Centineo, G.; Fragala, I.; Bruno, G.; Spampinato, S., Photoelectron spectroscopy of benzophenone, acetophenone and their ortho-alkyl derivatives, J. Mol. Struct., 1978, 44, 203. [all data]

Koenig, Wielesek, et al., 1977
Koenig, T.; Wielesek, R.; Miller, L.L.; So, Y.-H., Correlation of electrochemical reactivity and photoelectron spectra of aromatic ketones, J. Am. Chem. Soc., 1977, 99, 7061. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Rao, 1975
Rao, C.N.R., Lone-pair ionization bands of chromophores in the photoelectron spectra of organic molecules, Indian J. Chem., 1975, 13, 950. [all data]

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]

Foffani, Pignataro, et al., 1963
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Mass spectra of diazocompounds. I. Diazocarbonyl compounds, Nuovo Cimento, 1963, 29, 918. [all data]

Johnstone and Mellon, 1972
Johnstone, R.A.W.; Mellon, F.A., Electron-impact ionization and appearance potentials, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1209. [all data]

Helal and Zahran, 1978
Helal, A.I.; Zahran, N.F., Kinetic shift in some para-substituted acetophenones, Org. Mass Spectrom., 1978, 13, 549. [all data]

Buchs, Rossetti, et al., 1964
Buchs, A.; Rossetti, G.P.; Susz, B.P., Etude, en fonction de la constante σp de Hammett, du spectre de masse d'acetophenones p-substituees, Helv. Chim. Acta, 1964, 47, 1563. [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]

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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References