Journal
ORGANIC LETTERS
Volume 5, Issue 7, Pages 1135-1138Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol034247n
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[GRAPHIC] We report a study of the interaction between methylmethanetriacetic acid (MMTA) and a tripodal amidopyridine receptor 1, where the geometry of the binding is in part governed by a weak C-H/pi interaction in the presence of six strong N(O)-H...O(N) hydrogen bonds. There are two possible binding geometries for the 1:1 complex 1.MMTA; combining computational and experimental evidence we demonstrate that the endo binding mode is more favorable as the result of a C-H/pi interaction.
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