Jump to main content
Jump to site search

Issue 5, 1989
Previous Article Next Article

β-Diketone interactions. Part 8. The hydrogen bonding of the enol tautomers of some 3-substituted pentane-2,4-diones

Abstract

Three new derivatives of pentane-2,4-dione (PD) have been synthesized: 3-(4-nitrophenyl), 3-(4-phenoxyphenyl) and 3-(4-isopropylphenyl). The X-ray crystal structures of these compounds show them to have very short hydrogen bonds with R(O ⋯ O)= 2.445, 2.443, and 2.419 Å, respectively. Those parameters most sensitive to hydrogen bonding—1H chemical shift, change in chemical shift on deuteriation [Δδ(H, D)], and stretching frequencies [νC[double bond, length half m-dash]O and νmax.(OHO)]—have been measured for these, and other 3-derivatives of PD, with a view to probing the potential energy well of this type of bond. The conclusion is that in all of the compounds with R(O ⋯ O) < 2.45 Å, the hydrogen bonding is very strong with the proton zero point energy above the internal barrier.

Back to tab navigation

Article type: Paper
DOI: 10.1039/P29890000527
Citation: J. Chem. Soc., Perkin Trans. 2, 1989,0, 527-533
  •   Request permissions

    β-Diketone interactions. Part 8. The hydrogen bonding of the enol tautomers of some 3-substituted pentane-2,4-diones

    J. Emsley, L. Y. Y. Ma, P. A. Bates, M. Motevalli and M. B. Hursthouse, J. Chem. Soc., Perkin Trans. 2, 1989, 0, 527
    DOI: 10.1039/P29890000527

Search articles by author

Spotlight

Advertisements