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Apparent donor-acceptor interaction between nitroaromatics and acetonitrile

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Abstract

The partitioning behavior of nitro-aromatics in octanol-water and acetonitrile/NaCl-saturated water was examined. The nitro group contribution is opposite in the two systems, from which two different bonding mechanisms were inferred. In addition to cavity effects the octanol-water system is characterized by H-bonding of water to the nitro groups, while in the acetonitrile/NaCl-saturated water system electron donor-acceptor complexation predominates. A linear free energy relationship which relates the partition coefficients in the two systems was logP aw =0.727 logP ow +0.395 n+0.742 where n is the number of nitro groups per ring.

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Authors and Affiliations

  1. U. S. Army Cold Regions Research and Engineering Laboratory, 03755, Hanover, NH

    Daniel C. Leggett, Paul H. Miyares & Thomas F. Jenkins

Authors
  1. Daniel C. Leggett
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  2. Paul H. Miyares
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  3. Thomas F. Jenkins
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Leggett, D.C., Miyares, P.H. & Jenkins, T.F. Apparent donor-acceptor interaction between nitroaromatics and acetonitrile. J Solution Chem 21, 105–108 (1992). https://doi.org/10.1007/BF00648983

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  • DOI: https://doi.org/10.1007/BF00648983

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