Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Structural and Conformational Studies of ortho-, meta-, and para-Methyl Red upon Proton Gain and Loss

  • Park, Sun-Kyung (Thin Film Materials Laboratory, Advanced Marterials Division, Korea Research Institute of Chemical Technology) ;
  • Lee, Choong-Keun (Department of Chemistry, Chungbuk National University) ;
  • Min, Kyung-Chul (Department of Chemistry, Chungbuk National University) ;
  • Lee, Nam-Soo (Department of Chemistry, Chungbuk National University)
  • Published : 2005.08.20
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Abstract

The structures and conformations of ortho-, meta-, and para-methyl red (MR) upon proton gain and loss were studied by density functional calculations, and compared to methyl yellow for the effects of a carboxyl substitution. Internal hydrogen bonding causes the geometry of neutral o-MR planar, otherwise twist. Monoprotonated species of MR are planar where the proton is attached to $\beta$-azo nitrogen. This loses its azo character a bit, and shows strong delocalization characterized as a quinonoid canonical structure. Di-protonated species of MR is proved to hold two protons at the amino and $\alpha$-azo nitrogen atoms, and planar. It regains somewhat of its azo character, but still shows fairly delocalized property in terms of carbocationic canonical structures. The carboxyl substitution on 4-dimethylamino-trans-azobenzene structure has some delocalization effects on the geometry or conformation of MR derivatives whether neutral, mono-, di- or de-protonated.

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References

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