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      A Molecular Seesaw Balance: Evaluation of Solvent and Counteranion Effects on Pyridinium−π Interactions

      1 , 1 , 1

      Organic Letters

      American Chemical Society (ACS)

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          Abstract

          A molecular seesaw balance 1·MeI has been developed to measure pyridinium-π interactions. This balance adopts two distinct conformers, A and B, which are stabilized by a cation-π interaction and a π-π interaction, respectively. The conformer ratio was determined on the basis of the averaged (3)J coupling constants for H1-C-C-H2 and the corresponding boundary J values for conformers A and B. The effects of the solvent and the counteranion on the ΔG values were investigated using this molecular balance. Thermodynamic parameters obtained from a van't Hoff plot helped us to better understand the solvent and counteranion effects.

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          Author and article information

          Journal
          Organic Letters
          Org. Lett.
          American Chemical Society (ACS)
          1523-7060
          1523-7052
          September 11 2015
          October 02 2015
          September 14 2015
          October 02 2015
          : 17
          : 19
          : 4862-4865
          Affiliations
          [1 ]Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo112-8610, Japan
          Article
          10.1021/acs.orglett.5b02420
          26365626
          © 2015
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