A Combined Experimental and Theoretical Study of Anion–π Interactions in Bis(pyr­imidine) Salts

We report the synthesis and X-ray characterization of an N,N′-tetramethylenebis(2-aminopyrimidinium) tetrafluoroborate salt that exhibits anion–π interactions that are responsible for the crystal packing. The anion forms a sandwich complex with two pyrimidine rings. When the anion is nitrate, the crystal packing is governed by anion–π interactions and hydrogen bonds, and the sandwich complex is not formed. Finally, a theoretical study of the anion–π interactions in charged pyrimidine rings is in good agreement with the experimental findings. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

[1]  S. Matile,et al.  Rigid-rod anion-pi slides for multiion hopping across lipid bilayers. , 2007, Organic & biomolecular chemistry.

[2]  L. Hanton,et al.  A coordination polymer strategy for anion encapsulation: anion-pi interactions in (4,4) nets formed from Ag(I) salts and a flexible pyrimidine ligand. , 2007, Chemical communications.

[3]  D. Quiñonero,et al.  A theoretical study of anion-pi interactions in seven-membered rings. , 2007, Chemphyschem : a European journal of chemical physics and physical chemistry.

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

[5]  P. Ballester,et al.  Solid-state self-assembly of a calix[4]pyrrole-resorcinarene hybrid into a hexameric cage. , 2007, Journal of the American Chemical Society.

[6]  E. Knapp,et al.  Protonation states of ammonia/ammonium in the hydrophobic pore of ammonia transporter protein AmtB. , 2007, Journal of the American Chemical Society.

[7]  D. Quiñonero,et al.  Interplay Between Cation–π, Anion–π and π–π Interactions , 2006 .

[8]  S. Matile,et al.  Rigid oligonaphthalenediimide rods as transmembrane anion-pi slides. , 2006, Journal of the American Chemical Society.

[9]  M. Mascal.  Precedent and theory unite in the hypothesis of a highly selective fluoride receptor. , 2006, Angewandte Chemie.

[10]  J. Bacsa,et al.  Anion dependence of Ag(I) reactions with 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine (bptz): isolation of the molecular propeller compound [Ag2(bptz)3][AsF6]2. , 2005, Chemical communications.

[11]  E. Molins,et al.  Ag(I) complexes with alkylidene-bis(2-aminopyrimidines) as building units for discrete metallomacrocyclic frames. A structural and solution study. , 2005, Dalton transactions.

[12]  D. Quiñonero,et al.  Anion–π Interactions in Cyanuric Acids: A Combined Crystallographic and Computational Study , 2005 .

[13]  D. Quiñonero,et al.  Approximate Additivity of Anion−π Interactions: An Ab Initio Study on Anion−π, Anion−π2 and Anion−π3 Complexes , 2005 .

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

[15]  J. Reedijk,et al.  Crystal packing driven by metal-ligand interactions, hydrogen bonds, π-π stacking and anion-π stacking , 2005 .

[16]  D. Quiñonero,et al.  A Theoretical ab initio Study of the Capacity of Several Binding Units for the Molecular Recognition of Anions , 2005 .

[17]  J. Reedijk,et al.  An aromatic anion receptor: anion-pi interactions do exist. , 2004, Angewandte Chemie.

[18]  S. Lindeman,et al.  Halide recognition through diagnostic "anion-pi" interactions: molecular complexes of Cl-, Br-, and I- with olefinic and aromatic pi receptors. , 2004, Angewandte Chemie.

[19]  F. Meyer,et al.  Anion-pi interactions in a carousel copper(II)-triazine complex. , 2004, Journal of the American Chemical Society.

[20]  D. Quiñonero,et al.  Dual binding mode of s-triazine to anions and cations. , 2003, Organic letters.

[21]  F. Diederich,et al.  Interactions with aromatic rings in chemical and biological recognition. , 2003, Angewandte Chemie.

[22]  D. Quiñonero,et al.  s-Tetrazine as a new binding unit in molecular recognition of anions , 2003 .

[23]  David Quiñonero,et al.  Anion-pi Interactions: do they exist? , 2002, Angewandte Chemie.

[24]  Leonard J Barbour,et al.  Lariat ether receptor systems show experimental evidence for alkali metal cation-pi interactions. , 2002, Accounts of chemical research.

[25]  José Elguero,et al.  Interaction of anions with perfluoro aromatic compounds. , 2002, Journal of the American Chemical Society.

[26]  Michael D Bartberger,et al.  Anion-aromatic bonding: a case for anion recognition by pi-acidic rings. , 2002, Journal of the American Chemical Society.

[27]  Leonard J. Barbour,et al.  Macrocyclic polyethers as probes to assess and understand alkali metal cation-π interactions , 2001 .

[28]  G. Gokel,et al.  Experimental Evidence for Alkali Metal Cation−π Interactions , 2000 .

[29]  D. Quiñonero,et al.  Squaramide as a binding unit in molecular recognition , 2000 .

[30]  D. A. Dougherty,et al.  Cation-π interactions in structural biology , 1999 .

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

[32]  F. Javier Luque,et al.  Polarization effects in generalized molecular interaction potential: New Hamiltonian for reactivity studies and mixed QM/MM calculations , 1998 .

[33]  D. A. Dougherty,et al.  The Cationminus signpi Interaction. , 1997, Chemical reviews.

[34]  Modesto Orozco,et al.  Role of the tautomerism of 2-azaadenine and 2-azahypoxanthine in substrate recognition by xanthine oxidase , 1997, J. Comput. Aided Mol. Des..

[35]  D. A. Dougherty,et al.  Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp , 1996, Science.

[36]  D. Beglov,et al.  Finite representation of an infinite bulk system: Solvent boundary potential for computer simulations , 1994 .

[37]  R. MacKinnon,et al.  Mutations in the K+ channel signature sequence. , 1994, Biophysical journal.

[38]  D A Dougherty,et al.  A mechanism for ion selectivity in potassium channels: computational studies of cation-pi interactions. , 1993, Science.

[39]  F. Javier Luque,et al.  Molecular interaction potential: A new tool for the theoretical study of molecular reactivity , 1993, J. Comput. Chem..

[40]  F. J. Luque,et al.  Reactivity of planar and twisted amides in vacuum and aqueous environments: an ab initio MEP study , 1993 .

[41]  J M Thornton,et al.  Pi-pi interactions: the geometry and energetics of phenylalanine-phenylalanine interactions in proteins. , 1991, Journal of molecular biology.

[42]  Christopher A. Hunter,et al.  The nature of .pi.-.pi. interactions , 1990 .

[43]  Michelle Francl,et al.  Polarization corrections to electrostatic potentials , 1985 .