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Issue 17, 1992
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Effects of protonation on acetone: nuclear magnetic resonance and ab initio studies

Abstract

The electronic and geometric structural changes of acetone upon protonation are studied by 13C NMR spectroscopy and by molecular orbital (MO) calculations using the LORG (local orbital/local origin) method to calculate chemical shieldings and the CLOPPA (contributions for localized orbitals within the polarised propagator approach) analysis of the J coupling constants. In protonated acetone the 13C NMR spectrum has been resolved and two different methyl resonances (1.2 ppm apart) have been assigned. The one-bond C–C coupling constants between the carbonyl carbon and the methyl carbons differ by 4.5 Hz. The CLOPPA method was employed to study the orientational effect of the unprotonated oxygen lone pair on the coupling constants. Full ab initio optimized geometries at the 6-31G**/MP2 level are reported for acetone, its mono- and di-protonated species, the relative stabilities are discussed and geometries and Mulliken charge distributions are compared.

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Article type: Paper
DOI: 10.1039/FT9928802459
Citation: J. Chem. Soc., Faraday Trans., 1992,88, 2459-2463
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    Effects of protonation on acetone: nuclear magnetic resonance and ab initio studies

    L. B. Krivdin, S. V. Zinchenko, G. A. Kalabin, J. C. Facelli, M. F. Tufró, R. H. Contreras, A. Yu. Denisov, O. A. Gavrilyuk and V. I. Mamatyuk, J. Chem. Soc., Faraday Trans., 1992, 88, 2459
    DOI: 10.1039/FT9928802459

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