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'Intermolecular Hydrogen Bond' in keywords Facet   Publication Year 2000  [X]
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1Author    TeresaB. Orow Iaka, IrenaW. Olska3, A.Rtur Korzańskia, W. Olfgang, M. Iliusb, W. Olfgang Schnickb, W. Iesław, A. Ntkow IakcRequires cookie*
 Title    A Comparison of the Enamino Carbonyl Conjugation Efficiency for Hy­ drogen Bonding Formation in Pyridone and Dihydropyridone Systems  
 Abstract    The crystal structures of two compounds containing enaminone heterodiene systems and forming intermolecular hydrogen bonds N-H--O are reported: 1) 3-ethoxycarbonyl-2-methyl-4-pyridone (hereafter ETPY) and 2) 3-ethoxycarbonyl-2-phenyl-6-methoxycarbonyl-5,6-di-hydro-4-pyridone (hereafter EPPY). The crystal packing is controlled by intermolecular hydro­ gen bonds N-H-0 = C connecting the heteroconjugated enaminone groups in infinite chains. In ETPY crystals the intermolecular hydrogen bond involves the heterodienic pathway with the highest 7r-delocalization that is effective fo ra very short N -O distance of 2.701(9) A (average from two molecules in the asymmetric unit). Probably due to the steric hindrance, the hydrogen bond in EPPY is formed following the heterodienic pathway that involves the ester C = 0 group, although 7r-delocalization along this pathway is less than that along the pyridone-part pathway resulting in a longer N -O distance of 2.886(3) A. In tro d u c tio n 
  Reference    (Z. Naturforsch. 55b, 5—11 [2000]; received August 8 1999) 
  Published    2000 
  Keywords    Pyridone, Dihydropyridone, Enaminone 7r-Conjugated System, Intermolecular Hydrogen Bond, Steric Hindrance 
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 TEI-XML for    default:Reihe_B/55/ZNB-2000-55b-0005.pdf 
 Identifier    ZNB-2000-55b-0005 
 Volume    55