Methyl group effect on the proton affinity of methylated acetophenones studied by two mass spectrometric techniques

Kukol A, Strehle F, Thielking G, Grützmacher H-F (1993)
Organic Mass Spectrometry 28(10): 1107-1110.

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Abstract / Bemerkung
The proton affinities (PA) of all isomeric dimethylacetophenones were determined using the 'kinetic method' with a tandem mass spectrometer and by measurements of the proton transfer equilibrium in the gas phase by Fourier transform ion cyclotron resonance mass spectrometry. For both methods acetophenone and p-methylacetophenone, with well known PA values, were used as reference bases. Both methods yielded identical PA values for all dimethylacetophenones. The PA of the dimethylacetophenones were in a narrow range between 872 and 880 kJ mol-1 except for 2,6-dimethylacetophenone, for which a PA of 856 kJ mol-1 was found. The results are discussed in terms of possible mesomeric structures stabilizing the positive charge with regard to the substitution pattern in the phenyl ring. Obviously, the significant smaller PA of 2,6-dimethylacetophenone compared with the other isomers is due to the distortion of the conjugation of the C-O double bond with the aromatic pi system.
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Zeitschriftentitel
Organic Mass Spectrometry
Band
28
Zeitschriftennummer
10
Seite
1107-1110
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Kukol A, Strehle F, Thielking G, Grützmacher H-F. Methyl group effect on the proton affinity of methylated acetophenones studied by two mass spectrometric techniques. Organic Mass Spectrometry. 1993;28(10):1107-1110.
Kukol, A., Strehle, F., Thielking, G., & Grützmacher, H. - F. (1993). Methyl group effect on the proton affinity of methylated acetophenones studied by two mass spectrometric techniques. Organic Mass Spectrometry, 28(10), 1107-1110. doi:10.1002/oms.1210281021
Kukol, A., Strehle, F., Thielking, G., and Grützmacher, H. - F. (1993). Methyl group effect on the proton affinity of methylated acetophenones studied by two mass spectrometric techniques. Organic Mass Spectrometry 28, 1107-1110.
Kukol, A., et al., 1993. Methyl group effect on the proton affinity of methylated acetophenones studied by two mass spectrometric techniques. Organic Mass Spectrometry, 28(10), p 1107-1110.
A. Kukol, et al., “Methyl group effect on the proton affinity of methylated acetophenones studied by two mass spectrometric techniques”, Organic Mass Spectrometry, vol. 28, 1993, pp. 1107-1110.
Kukol, A., Strehle, F., Thielking, G., Grützmacher, H.-F.: Methyl group effect on the proton affinity of methylated acetophenones studied by two mass spectrometric techniques. Organic Mass Spectrometry. 28, 1107-1110 (1993).
Kukol, A., Strehle, F., Thielking, Gerhard, and Grützmacher, Hans-Friedrich. “Methyl group effect on the proton affinity of methylated acetophenones studied by two mass spectrometric techniques”. Organic Mass Spectrometry 28.10 (1993): 1107-1110.
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