Weak Intermolecular Anion–π Interactions in Pentafluorobenzyl-Substituted Ammonium Betaines

A series of ammonium–carboxylate and ammonium–sulfonate betaines was synthesized and studied by single-crystal X-ray diffraction analysis to investigate the weak intermolecular interactions as well as the intramolecular interactions in the solid state. None of the expected intramolecular anion–π interactions could be observed, probably because of the steric demands and the reduced nucleophilicity of the anionic part of the betaines. Nevertheless, a weak intermolecular anion–π interaction between the anionic part of the betaine and the pentafluorophenyl unit is present in the structure of 5a.

[1]  K. Rissanen,et al.  Geometrically diverse anions in anion–π interactions , 2012 .

[2]  K. Rissanen,et al.  From attraction to repulsion: anion-π interactions between bromide and fluorinated phenyl groups. , 2011, Chemical communications.

[3]  L. Salonen,et al.  Aromatische Ringe in chemischer und biologischer Erkennung: Energien und Strukturen , 2011 .

[4]  Ernst-Walter Knapp,et al.  Recent advances in anion–π interactions , 2011 .

[5]  M. Mayor,et al.  Experimental evidence for the functional relevance of anion-pi interactions. , 2010, Nature chemistry.

[6]  K. Rissanen,et al.  CH-directed anion-pi interactions in the crystals of pentafluorobenzyl-substituted ammonium and pyridinium salts. , 2010, Chemistry.

[7]  B. Hay,et al.  Anion-arene adducts: C-H hydrogen bonding, anion-pi interaction, and carbon bonding motifs. , 2008, Chemical communications.

[8]  K. Rissanen,et al.  Structural versatility of anion-pi interactions in halide salts with pentafluorophenyl substituted cations. , 2008, Journal of the American Chemical Society.

[9]  H. Schneider,et al.  Aromatic molecules in anion recognition: electrostatics versus H-bonding. , 2007, Journal of the American Chemical Society.

[10]  S. Teat,et al.  Anion binding involving pi-acidic heteroaromatic rings. , 2007, Accounts of chemical research.

[11]  Orion B. Berryman,et al.  Anion-pi interaction augments halide binding in solution. , 2006, Chemical communications.

[12]  K. Holman,et al.  Selective anion encapsulation by a metalated cryptophane with a pi-acidic interior. , 2005, Journal of the American Chemical Society.

[13]  Maria Cristina Burla,et al.  SIR2004: an improved tool for crystal structure determination and refinement , 2005 .

[14]  A. Osuka,et al.  Anion Binding Properties of N-Confused Porphyrins at the Peripheral Nitrogen , 2004 .

[15]  François Diederich,et al.  Wechselwirkungen mit aromatischen Ringen in chemischen und biologischen Erkennungsprozessen , 2003 .

[16]  Louis J. Farrugia,et al.  WinGX suite for small-molecule single-crystal crystallography , 1999 .

[17]  J. Atwood,et al.  Anion Binding within the Cavity of π-Metalated Calixarenes , 1997 .

[18]  K. Hiraoka,et al.  High-symmetric structure of the gas-phase cluster ions X-.cntdot..cntdot..cntdot.C6F6 (X = Cl, Br, and I) , 1987 .

[19]  K. Hiraoka,et al.  A determination of the stabilities and structures of F−(C6H6) and F−(C6F6) clusters , 1987 .

[20]  K. Dunbar,et al.  Anion-pi interactions. , 2008, Chemical Society reviews.

[21]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[22]  P. Ballester.  Anions and π-Aromatic Systems. Do They Interact Attractively? , 2007 .

[23]  H. Furuta,et al.  N-confused porphyrins as new scaffolds for supramolecular architecture , 2004 .