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Weak C-H/pi interaction participates in the diastereoselectivity of a host-guest complex in the presence of six strong hydrogen bonds.

Authors
  • Frontera, Antonio1
  • Garau, Carolina
  • Quiñonero, David
  • Ballester, Pablo
  • Costa, Antoni
  • Deyà, Pere M
  • 1 Departament de Química, Universitat de les Illes Balears, Crta. de Valldemossa km 7.5, 07122 Palma de Mallorca, Spain. [email protected] , (Spain)
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Apr 03, 2003
Volume
5
Issue
7
Pages
1135–1138
Identifiers
PMID: 12659592
Source
Medline
License
Unknown

Abstract

[structure: see text] 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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