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Acetophenone, 3'-chloro-


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

Data compiled as indicated in comments:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
Proton affinity (review)846.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity815.1kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.616 ± 0.087IMREMishima, Huh, et al., 1995«DELTA»Gea(343 K) = -14.5 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B
0.585 ± 0.087IMREHuh, Kang, et al., 1999«DELTA»G(EA) 343K; anchored to «DELTA»G value. Including anchor «DELTA»S, EA is ca. 0.4 kcal/mol more bound.; B
0.5832 ± 0.0056ECDSteelhammer and Wentworth, 1969B

Ionization energy determinations

IE (eV) Method Reference Comment
9.5 ± 0.1EIChin and Harrison, 1969RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H4OCl+10.4 ± 0.1CH3EIChin and Harrison, 1969RDSH

De-protonation reactions

C8H6ClO- + Hydrogen cation = Acetophenone, 3'-chloro-

By formula: C8H6ClO- + H+ = C8H7ClO

Quantity Value Units Method Reference Comment
Deltar1495. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1466. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

References

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

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]

Mishima, Huh, et al., 1995
Mishima, M.; Huh, C.; Lee, H.W.; Nakamura, H.; Fujio, M.; Tsuno, Y., Electron affinities of acetophenones and methyl benzoates. Varying resonance demand of aromatic radical anions, Tetrahed. Lett., 1995, 36, 13, 2265, https://doi.org/10.1016/0040-4039(95)00267-G . [all data]

Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S., Electron affinities and electron transfer reactions, Chem. Rev., 1987, 87, 513. [all data]

Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H., Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase, Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083 . [all data]

Steelhammer and Wentworth, 1969
Steelhammer, J.C.; Wentworth, W.E., Correlation of Electron Beam and Thermal Electron Attachment Studies for Some Chloro, Bromo, Iodo Aromatic Compounds, J. Chem. Phys., 1969, 51, 5, 1802, https://doi.org/10.1063/1.1672262 . [all data]

Chin and Harrison, 1969
Chin, M.S.; Harrison, A.G., Substituent effects on ion abundances and energetics in substituted acetophenones, Org. Mass Spectrom., 1969, 2, 1073. [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]


Notes

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