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A Comparison of the Enamino Carbonyl Conjugation Efficiency for Hydrogen Bonding Formation in Pyridone and Dihydropyridone Systems
-
Teresa Borowiak
,
Irena Wolska
Veröffentlicht/Copyright:
2. Juni 2014
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·O = C connecting the heteroconjugated enaminone groups in infinite chains. In ETPY crystals the intermolecular hydrogen bond involves the heterodienic pathway with the highest π-delocalization that is effective for a very short N·O distance of 2.701(9) Å (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 = O group, although π-delocalization along this pathway is less than that along the pyridone-part pathway resulting in a longer N·O distance of 2.886(3) Å
: Pyridone; Dihydropyridone; Enaminone π-Conjugated System; Intermolecular Hydrogen Bond; Steric Hindrance
Received: 1999-8-8
Published Online: 2014-6-2
Published in Print: 2000-1-1
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
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Artikel in diesem Heft
- Masthead
- Contents
- Alkylsubstituierte Cyclopentadienylvanadium(V)-Komplexe: tC4H9N=VCpRCl2 / Alkylated Cyclopentadienylvanadium (V) Complexes: tC4H9N =VCpRC l2
- A Comparison of the Enamino Carbonyl Conjugation Efficiency for Hydrogen Bonding Formation in Pyridone and Dihydropyridone Systems
- peri-Interactions in Naphthalenes, 3 [1]. On Hypercoordination in 8-Dimethylamino-naphth-1-yl-phosphonium salts and -phosphines
- Untersuchungen zur Thermolyse von Si2OCl6 / Thermolysis of Si2OCl6
- Chemischer Transport fester Lösungen am Beispiel von Mischspineilen / Chemical Transport of Solid Solutions: Mixed Spinels
- Phenylmercury Chloride: Its Single-Crystal X-Ray Structure and Some Aspects of its Biological Chemistry
- Preparation and Crystal Structure of Na4TiSe4. A Selenotitanate with Discrete Tetrahedral Anions
- Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von (Ph3PNPPh3)[OsF5Cl]·CH2Cl2 und cis-(Ph3PNPPh3)[OsF4Cl2]·CH2Cl2 / Crystal Structures, Vibrational Spectra and Normal Coordinate Analysis of (Ph3PNPPh3) [OsF5Cl]·CH2Cl2 and cis-(Ph3PNPPh3 )[OsF4Cl2]·CH2Cl2
- Synthese, Struktur und Reaktivität von Aminomethylpyridin- zinkdihalogeniden / Synthesis, Structure and Reactivity of Aminomethylpyridine Zinc Dihalides
- Singly Charged λ6Si-Silicate Anions with an SiF5C Skeleton: Syntheses and Crystal Structure Analyses of the Ionic Hexacoordinate Silicon Compounds [Me3NH][F5SiCH2NMe2H]·H2O and [Me3NH][F5SiCH2NMe2H]·H2O
- Thermische Zersetzung und Lösungskalorimetrie von Ammoniumneodymiodiden / Thermal Decomposition and Solution Calorimetry of Ammonium Neodymium Iodides
- Reaktionsbeteiligung elektrophiler Funktionen bei der Dehydrierung 4-substituierter Piperidine / Participation of Electrophilic Groups with the Dehydrogenation of 4-Substituted Piperidines
- Catalytic Oxidation of a Trialkyl-Substituted Phenol and Aniline with Biomimetic Schiff Base Complexes
- 2-Hexanoyl-1-tribromomethyl-1,2,3,4-tetrahydro-β-carboline: Crystal Structure Analysis of a Potent Inhibitor of Complex I of Mitochondrial Respiration
- Chemical Constituents of Ajuga parviflora
- Amino Acid Derivatives in Organic Synthesis, Part 4 [1]: Facile Synthesis of Heterocycles Containing a Glycine Residue
- Di-tert-alkyl Nitroxyl Radicals. Synthesis, Physical Properties and Applications as Inhibitors of Vinyl Polmerization at Elevated Temperatures
- A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
Artikel in diesem Heft
- Masthead
- Contents
- Alkylsubstituierte Cyclopentadienylvanadium(V)-Komplexe: tC4H9N=VCpRCl2 / Alkylated Cyclopentadienylvanadium (V) Complexes: tC4H9N =VCpRC l2
- A Comparison of the Enamino Carbonyl Conjugation Efficiency for Hydrogen Bonding Formation in Pyridone and Dihydropyridone Systems
- peri-Interactions in Naphthalenes, 3 [1]. On Hypercoordination in 8-Dimethylamino-naphth-1-yl-phosphonium salts and -phosphines
- Untersuchungen zur Thermolyse von Si2OCl6 / Thermolysis of Si2OCl6
- Chemischer Transport fester Lösungen am Beispiel von Mischspineilen / Chemical Transport of Solid Solutions: Mixed Spinels
- Phenylmercury Chloride: Its Single-Crystal X-Ray Structure and Some Aspects of its Biological Chemistry
- Preparation and Crystal Structure of Na4TiSe4. A Selenotitanate with Discrete Tetrahedral Anions
- Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von (Ph3PNPPh3)[OsF5Cl]·CH2Cl2 und cis-(Ph3PNPPh3)[OsF4Cl2]·CH2Cl2 / Crystal Structures, Vibrational Spectra and Normal Coordinate Analysis of (Ph3PNPPh3) [OsF5Cl]·CH2Cl2 and cis-(Ph3PNPPh3 )[OsF4Cl2]·CH2Cl2
- Synthese, Struktur und Reaktivität von Aminomethylpyridin- zinkdihalogeniden / Synthesis, Structure and Reactivity of Aminomethylpyridine Zinc Dihalides
- Singly Charged λ6Si-Silicate Anions with an SiF5C Skeleton: Syntheses and Crystal Structure Analyses of the Ionic Hexacoordinate Silicon Compounds [Me3NH][F5SiCH2NMe2H]·H2O and [Me3NH][F5SiCH2NMe2H]·H2O
- Thermische Zersetzung und Lösungskalorimetrie von Ammoniumneodymiodiden / Thermal Decomposition and Solution Calorimetry of Ammonium Neodymium Iodides
- Reaktionsbeteiligung elektrophiler Funktionen bei der Dehydrierung 4-substituierter Piperidine / Participation of Electrophilic Groups with the Dehydrogenation of 4-Substituted Piperidines
- Catalytic Oxidation of a Trialkyl-Substituted Phenol and Aniline with Biomimetic Schiff Base Complexes
- 2-Hexanoyl-1-tribromomethyl-1,2,3,4-tetrahydro-β-carboline: Crystal Structure Analysis of a Potent Inhibitor of Complex I of Mitochondrial Respiration
- Chemical Constituents of Ajuga parviflora
- Amino Acid Derivatives in Organic Synthesis, Part 4 [1]: Facile Synthesis of Heterocycles Containing a Glycine Residue
- Di-tert-alkyl Nitroxyl Radicals. Synthesis, Physical Properties and Applications as Inhibitors of Vinyl Polmerization at Elevated Temperatures
- A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
