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) A,β=115.44(3)°,Z=4,V=729.4 A3, andR=0.046 (1660 reflections).
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