Are C−H Groups Significant Hydrogen Bonding Sites in Anion Receptors? Benzene Complexes with Cl-, NO3-, and ClO4-

The first redox-active halogen bonding anion receptors display larger electrochemical voltammetric responses to halide binding compared to their hydrogen bonding analogues.

Download Full-text

Sugar Thioureas as Anion Receptors. Effect of Intramolecular Hydrogen Bonding in the Carboxylate Binding Properties of Symmetric Sugar Thioureas

Organic Letters ◽

10.1021/ol990889s ◽

1999 ◽

Vol 1 (8) ◽

pp. 1217-1220 ◽

Cited By ~ 39

Author(s):

José L. Jiménez Blanco ◽

Juan M. Benito ◽

Carmen Ortiz Mellet ◽

José M. García Fernández

Keyword(s):

Hydrogen Bonding ◽

Intramolecular Hydrogen Bonding ◽

Anion Receptors ◽

Binding Properties ◽

Intramolecular Hydrogen

Download Full-text

Ferrocenyl imidazolium salts as a new class of anion receptors with C–H···X− hydrogen bonding

Tetrahedron Letters ◽

10.1016/s0040-4039(99)02072-9 ◽

2000 ◽

Vol 41 (3) ◽

pp. 413-416 ◽

Cited By ~ 68

Author(s):

Jean-Luc Thomas ◽

Joshua Howarth ◽

Keith Hanlon ◽

Damien McGuirk

Keyword(s):

Hydrogen Bonding ◽

Anion Receptors ◽

Imidazolium Salts ◽

New Class

Download Full-text

Hydrogen-bonding pyrrolic amide cleft anion receptors

Tetrahedron Letters ◽

10.1016/s0040-4039(01)00896-6 ◽

2001 ◽

Vol 42 (30) ◽

pp. 5095-5097 ◽

Cited By ~ 61

Author(s):

Philip A Gale ◽

Salvatore Camiolo ◽

Christopher P Chapman ◽

Mark E Light ◽

Michael B Hursthouse

Keyword(s):

Hydrogen Bonding ◽

Anion Receptors

Download Full-text

Experimental and Theoretical Evidence of the Bidentate Binding Mode of Dichloroacetamido Groups at the Upper Rim of Calix[4]arene Hydrogen-Bonding Anion Receptors

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20041063 ◽

2004 ◽

Vol 69 (5) ◽

pp. 1063-1079 ◽

Cited By ~ 9

Author(s):

Alessandro Casnati ◽

Francesca Bonetti ◽

Francesco Sansone ◽

Franco Ugozzoli ◽

Rocco Ungaro

Keyword(s):

Hydrogen Bonding ◽

Binding Mode ◽

Association Constants ◽

Anion Binding ◽

Anion Receptors ◽

Binding Properties ◽

Carboxylate Anions ◽

Molecular Modeling Studies ◽

Theoretical Evidence ◽

Upper Rim

Calix[4]arenes in the 1,3-alternate conformation (1-3) and bearing activated amide groups at the upper rim have been synthesized and their anion binding properties studied and compared with conformationally mobile (4) or cone (Ib) receptors having the same binding groups. Association constants determined in CDCl3 show a stronger complexation for Y-shaped carboxylate anions and a higher efficiency for receptors (Ib and 3) bearing dichloroacetamido moieties as hydrogen bonding donor groups. Molecular modeling studies performed on the cone derivative (Ib) and its 1,3-alternate isomer (10) and ab initio calculations on 4-methoxyaniline derivatives (11-13) used as simplified models, reveal that the α,α-dichloroacetamido moieties bind anions in a bidentate fashion using both the N-H and the CHCl2 as hydrogen bonding donor groups. This explains the higher efficiency in carboxylate binding found for Ib and 3 that incorporate the dichloroacetamido binding unit in their structures.

Download Full-text