A Comparison of NH-π versus Lone Pair Hydrogen Bonding Effects on Carbon Acid pK_a Shifts

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This article has been cited by 11 ACS Journal articles (5 most recent appear below).

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  A Versatile Tripodal Amide Receptor for the Encapsulation of Anions or Hydrated Anions via Formation of Dimeric Capsules

  M. Arunachalam and Pradyut Ghosh
  Inorganic Chemistry2010 49 (3), 943-951

  • A Versatile Tripodal Amide Receptor for the Encapsulation of Anions or Hydrated Anions via Formation of Dimeric Capsules

    M. Arunachalam and Pradyut Ghosh
    Inorganic Chemistry2010 49 (3), 943-951

    A bowl-shaped tripodal receptor with an appropriately positioned amide functionality on the benzene platform and electron-withdrawing p-nitrophenyl terminals (L1) has been designed, synthesized, and studied for the anion binding properties. The single-...

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• 

  Strong N−H···π Hydrogen Bonding in Amide−Benzene Interactions

  Philipp Ottiger, Chantal Pfaffen, Roman Leist and Samuel Leutwyler, Rafał A. Bachorz and Wim Klopper
  The Journal of Physical Chemistry B2009 113 (9), 2937-2943

  • Strong N−H···π Hydrogen Bonding in Amide−Benzene Interactions

    Philipp Ottiger, Chantal Pfaffen, Roman Leist and Samuel Leutwyler, Rafał A. Bachorz and Wim Klopper
    The Journal of Physical Chemistry B2009 113 (9), 2937-2943

    Among the weak intermolecular interactions found in proteins, the amide N−H···π interaction has been widely observed but remains poorly characterized as an individual interaction. We have investigated the isolated supersonic-jet-cooled dimer of the cis-...

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• 

  Electrophilic Coordination Catalysis: A Summary of Previous Thought and a New Angle of Analysis

  Ronald J. T. Houk, Arthur Monzingo and Eric V. Anslyn
  Accounts of Chemical Research2008 41 (3), 401-410

  • Electrophilic Coordination Catalysis: A Summary of Previous Thought and a New Angle of Analysis

    Ronald J. T. Houk, Arthur Monzingo and Eric V. Anslyn
    Accounts of Chemical Research2008 41 (3), 401-410

    One of the most common, and yet least well understood, enzymatic transformations is proton abstraction from activated carbon acids such as carbonyls. Understanding the mechanism for these proton abstractions is basic to a good understanding of enzyme ...

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• 

  Molecular Rotors as Simple Models to Study Amide NH−Aromatic Interactions and Their Role in the Folding of Peptide-like Structures

  Ignacio Alfonso, M. Isabel Burguete, Francisco Galindo, Santiago V. Luis, and Laura Vigara
  The Journal of Organic Chemistry2007 72 (21), 7947-7956

  • Molecular Rotors as Simple Models to Study Amide NH−Aromatic Interactions and Their Role in the Folding of Peptide-like Structures

    Ignacio Alfonso, M. Isabel Burguete, Francisco Galindo, Santiago V. Luis, and Laura Vigara
    The Journal of Organic Chemistry2007 72 (21), 7947-7956

    The conformational behavior of designed macrocyclic naphthalenophanes (1a,b and 2a,b) derived from amino acids (Phe and Val) has been used for studying NH···π interactions. The cycles having 16- and 17-membered rings showed a dynamic process within the ...

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  Effects of Lysine Acetylation in a β-Hairpin Peptide:  Comparison of an Amide−π and a Cation−π Interaction

  Robert M. Hughes and Marcey L. Waters
  Journal of the American Chemical Society2006 128 (41), 13586-13591

  • Effects of Lysine Acetylation in a β-Hairpin Peptide:  Comparison of an Amide−π and a Cation−π Interaction

    Robert M. Hughes and Marcey L. Waters
    Journal of the American Chemical Society2006 128 (41), 13586-13591

    The acetylation of lysine is a common posttranslational modification of histone proteins, and the interaction of acetylated lysines with aromatic rings is commonly observed in transcriptionally relevant protein−protein interactions. To determine the ...

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