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Solution and solid-state hydrogen bond patterns ofo-methoxy- ando-ethoxybenzoic acids

  • Margaret C. Etter
  • Zofia Urbańczyk-Lipkowska
  • Patricia A. Fish
  • Thomas W. Panunto
  • Paul W. Baures
  • James S. Frye
Article

Abstract

The hydrogen bond patterns ofo-alkoxybenzoic acids have been shown previously to involve intramolecular hydrogen bonds. In this paper we show thato-methoxybenzoic acid (I) and o-ethoxybenzoic acid (II) both exist as monomers with intramolecular hydrogen bonds in solution but that, in the solid-state,I crystallizes as hydrogen-bonded dimers whileII crystallizes with an intramolecular hydrogen bond. The correlation between solution and solid-state hydrogen bond patterns is made using solution and solid-state IR and NMR methods and by correlating the solid-state patterns with known X-ray crystal structures. The crystal structure ofI is reported here. Crystal data: monoclinicP21/n;a=7.002(2),b=14.945(9),c=7.719(4) Å,β=115.44(3)°,Z=4,V=729.4 Å3, andR=0.046 (1660 reflections).

Keywords

Hydrogen Reflection Physical Chemistry Crystal Structure Hydrogen Bond 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • Margaret C. Etter
    • 1
  • Zofia Urbańczyk-Lipkowska
    • 1
  • Patricia A. Fish
    • 1
  • Thomas W. Panunto
    • 1
  • Paul W. Baures
    • 1
  • James S. Frye
    • 2
  1. 1.Department of ChemistryUniversity of MinnesotaMinneapolis
  2. 2.Colorado State University NMR CenterColorado

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