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Hydrogen bond-aromaticity cooperativity in self-assembling 4-pyridone chains

Anand, Megha ; Fernández, Israel ; Schaefer III, Henry F. ; Wu, Judy I-Chia

Journal of computational chemistry, 2016-01, Vol.37 (1), p.59-63 [Periódico revisado por pares]

United States: Blackwell Publishing Ltd

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  • Título:
    Hydrogen bond-aromaticity cooperativity in self-assembling 4-pyridone chains
  • Autor: Anand, Megha ; Fernández, Israel ; Schaefer III, Henry F. ; Wu, Judy I-Chia
  • Assuntos: Aromaticity ; Assembling ; Bonding ; Chains ; Chemical bonds ; Chemical engineering ; Chemistry ; Coupling ; Decomposition ; Electrons ; energy decomposition analysis ; Hydrogen ; hydrogen bonding ; Hydrogen bonds ; Hydrogen storage ; Nuclei ; nucleus independent chemical shifts ; Polarization ; self-assembly ; Series (mathematics)
  • É parte de: Journal of computational chemistry, 2016-01, Vol.37 (1), p.59-63
  • Notas: National Science Foundation - No. CHE-1057466; No. CHE-1361178
    istex:086712B123766DEA8E9528BF7183D2E62A203688
    ark:/67375/WNG-ZGJDSTWP-B
    Spanish MINECO-FEDER - No. CTQ2013-44303-P; No. CTQ2014-51912-REDC
    ArticleID:JCC23976
    ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Self‐assembling building blocks like the 4‐pyridone can exhibit extraordinary H‐bond‐aromaticity coupling effects. Computed dissected nucleus independent chemical shifts (NICS(1)zz), natural bond orbital (NBO) charges, and energy decomposition analyses (EDA) for a series of hydrogen (H‐) bonded 4‐pyridone chains (4‐py)n (n = 2 to 8) reveal that H‐bonding interactions can polarize the 4‐pyridone exocyclic C=O bonds and increase 4n+2 π‐electron delocalization in the six‐membered ring. The resulting H‐bonded 4‐pyridone units display enhanced π‐aromatic character (both magnetically and energetically) and their corresponding NH···OC interactions are strengthened. These π‐electron polarization effects do not depend on the relative orientations (co‐planar or perpendicular) of the neighboring 4‐pyridone units, but increase with the number of H‐bonded units. © 2015 Wiley Periodicals, Inc. Hydrogen bonding interactions can polarize the π‐systems of 4‐pyridones to increase cyclic (4n+2) π‐electron delocalization. The resulting H‐bonded six‐membered rings exhibit enhanced π‐aromaticity and the corresponding NH···OC interactions are strengthened. Extended H‐bonded 4‐pyridone chains exhibit high degrees of such cooperativity, even when each of the neighboring 4‐pyridone rings are twisted to preclude direct π‐overlap between the H‐bonded units.
  • Editor: United States: Blackwell Publishing Ltd
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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