Structural and theoretical studies of 4,4 '-[1,4-phenylene-bis(azanediyl)]dipent-3-en-2-one: evidence of a pi-delocalized keto-enamine

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Benjelloun O. T., AKKURT M., YILDIRIM S., Daoudi M., Ben Hadda T., Boukir A., ...More

ARKIVOC, pp.80-93, 2008 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Publication Date: 2008
  • Doi Number: 10.3998/ark.5550190.0009.210
  • Journal Name: ARKIVOC
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.80-93
  • Keywords: bis-N,O-ligand, tautomeric forms, geometrical parameters, DFT methods, BISACETYLACETONEETHYLENEDIIMINE, CHROMOPHORES, COMPLEXES, ANALOGS, DESIGN, TOOL
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

In this work we present the synthesis of 4,4'-[1,4-phenylene-bis(azanediyl)]dipent-3-en-2-one. Evidence is proposed for the presence of various tautomers of this molecule which are complemented with theoretical density functional theory (DFT)-B3LYP/6-31G* calculations to characterize the potential energy surface of these species. The experimentally observed 3b isomer crystallizes as an orthorhombic Pbcn structure; a = 10.8412(10) angstrom, b = 8.9205(7) angstrom, c = 14.9949(13) angstrom, V = 1450.1(2) angstrom(3), Z = 4 with a final R value is 0.038. From our X-Ray crystallographic analysis an intramolecular hydrogen N-H center dot center dot center dot O interaction is observed.