Competitive solvation of K+ by benzene and water: Cation-π interactions and π-hydrogen bonds

The competition between ion–molecule and hydrogen bond interactions in K+(benzene)1–5(water)1,2 is examined using infrared spectroscopic and mass spectrometric methods. The cation-π interaction and π-hydrogen bond play an important role in the structure of the mixed cluster ions. Important observations include: the preferential binding of benzene vs water to K+; the “dehydration” of the potassium ion by benzene; and the observation of water acting as a double proton donor with π-hydrogen bonds to two benzenes.

[1]  T. Zwier,et al.  Size-Specific Infrared Spectra of Benzene-(H2O)n Clusters (n = 1 through 7): Evidence for Noncyclic (H2O)n Structures , 1994, Science.

[2]  D. Baltimore,et al.  Crystal structure of the phosphotyrosine recognition domain SH2 of v-src complexed with tyrosine-phosphorylated peptides , 1993, Nature.

[3]  T. Zwier THE SPECTROSCOPY OF SOLVATION IN HYDROGEN-BONDED AROMATIC CLUSTERS , 1996 .

[4]  Axel Kulcke,et al.  Infrared spectroscopy of small size‐selected water clusters , 1996 .

[5]  Jan Sunner,et al.  Ion-solvent molecule interactions in the gas phase. The potassium ion and benzene , 1981 .

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

[7]  Kwang S. Kim,et al.  Ab initio study of the complexation of benzene with ammonium cations , 1995 .

[8]  J. Lisy,et al.  Solvation of ions in the gas-phase: a molecular dynamics simulation , 1996 .

[9]  J. Lisy,et al.  Vibrational predissociation spectroscopy of Cs+(H2O)1−5 , 1996 .

[10]  Sang Joo Lee,et al.  On Binding Forces between Aromatic Ring and Quaternary Ammonium Compound , 1994 .

[11]  K. Rao,et al.  High resolution infrared spectra of water vapor , 1969 .

[12]  Peter A. Kollman,et al.  Cation-.pi. Interactions: Nonadditive Effects Are Critical in Their Accurate Representation , 1995 .

[13]  Larry A. Curtiss,et al.  Studies of molecular association in H2O and D2O vapors by measurement of thermal conductivity , 1979 .

[14]  M. Levitt,et al.  Aromatic Rings Act as Hydrogen Bond Acceptors , 2022 .

[15]  E. A. Walters,et al.  Dissociation energy of the benzenewater van der Waals complex , 1995 .

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

[17]  Roger E Bumgarner,et al.  Benzene Forms Hydrogen Bonds with Water , 1992, Science.

[18]  J. Thornton,et al.  Amino/aromatic interactions in proteins: is the evidence stacked against hydrogen bonding? , 1994, Journal of molecular biology.

[19]  Sandro Mecozzi,et al.  Cation−π Interactions in Simple Aromatics: Electrostatics Provide a Predictive Tool , 1996 .

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

[21]  H. Krause,et al.  Binding Energy and Structure of van der Waals Complexes of Benzene , 1994 .

[22]  Timothy S. Zwier,et al.  Resonant ion-dip infrared spectroscopy of benzene–H2O and benzene–HOD , 1995 .

[23]  J. Lisy Spectroscopy and structure of solvated alkali-metal ions , 1997 .

[24]  K. Jordan,et al.  Infrared Spectrum of a Molecular Ice Cube: The S4 and D2d Water Octamers in Benzene-(Water)8 , 1997 .

[25]  Corey J. Weinheimer,et al.  Hydrogen bonding in metal ion solvation: vibrational spectroscopy of Cs+(CH3OH)1–6 in the 2.8 μm region , 1996 .