Aqueous imidazole solutions: a structural perspective from simulations with high-rank electrostatic multipole moments.

Imidazole is a small but important molecule occurring as a structure fragment in systems from amino acids, over ionic liquids, to synthetic polymers. Here we focus on the structure and dynamics of imidazole in water at ambient conditions, using both radial and spatial distribution functions. Molecular dynamics simulations were carried out for various imidazole concentrations, using a traditional point-charge potential and a high-rank multipolar potential. The difference in the description of the electrostatics leads to sizable quantitative differences (e.g., the diffusion coefficient) but also qualitative differences in the local structure. In contrast to a point-charge potential, the multipolar potential favors hydrogen-bonded chainlike imidazole dimers over stacked dimers.

[1]  G. Whitesides,et al.  Molecular self-assembly and nanochemistry: a chemical strategy for the synthesis of nanostructures. , 1991, Science.

[2]  Paul L. A. Popelier,et al.  Geometrically faithful homeomorphisms between the electron density and the bare nuclear potential , 2009 .

[3]  Paul L. A. Popelier,et al.  Simulation of liquid water using a high-rank quantum topological electrostatic potential , 2004 .

[4]  Douglas B Kell,et al.  Optimal construction of a fast and accurate polarisable water potential based on multipole moments trained by machine learning. , 2009, Physical chemistry chemical physics : PCCP.

[5]  Paul L. A. Popelier,et al.  A method to integrate an atom in a molecule without explicit representation of the interatomic surface , 1998 .

[6]  L. Rebelo,et al.  Ionic liquids: a pathway to environmental acceptability. , 2011, Chemical Society reviews.

[7]  R. Caminiti,et al.  Molecular aggregation phenomena in solution: an energy dispersive X-ray diffraction study of concentrated imidazole water solutions , 1999 .

[8]  P. Popelier,et al.  The prediction of energies and geometries of hydrogen bonded DNA base-pairs via a topological electrostatic potential , 2002 .

[9]  Bertrand Guillot,et al.  A reappraisal of what we have learnt during three decades of computer simulations on water , 2002 .

[10]  Paul L A Popelier,et al.  Beyond Point Charges: Dynamic Polarization from Neural Net Predicted Multipole Moments. , 2008, Journal of chemical theory and computation.

[11]  Anthony J. Stone,et al.  The Theory of Intermolecular Forces , 2013 .

[12]  Paul L. A. Popelier,et al.  High-rank quantum topological electrostatic potential: Molecular dynamics simulation of liquid hydrogen fluoride , 2003 .

[13]  P. Popelier,et al.  Dynamically Polarizable Water Potential Based on Multipole Moments Trained by Machine Learning. , 2009, Journal of chemical theory and computation.

[14]  P. Popelier,et al.  A convergent multipole expansion for 1,3 and 1,4 Coulomb interactions. , 2006, The Journal of chemical physics.

[15]  W. L. Jorgensen,et al.  Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids , 1996 .

[16]  Paul L. A. Popelier,et al.  Atom–atom partitioning of total (super)molecular energy: The hidden terms of classical force fields , 2007, J. Comput. Chem..

[17]  Jiyun C Huie.  Guided molecular self-assembly: a review of recent efforts , 2003 .

[18]  M. Suhm,et al.  Communication: Where does the first water molecule go in imidazole? , 2011, The Journal of chemical physics.

[19]  H. Berendsen,et al.  Molecular dynamics with coupling to an external bath , 1984 .

[20]  Paul L A Popelier,et al.  Properties and 3D Structure of Liquid Water:  A Perspective from a High-Rank Multipolar Electrostatic Potential. , 2008, Journal of chemical theory and computation.

[21]  P. Popelier,et al.  Convergence of the multipole expansion for 1,2 Coulomb interactions: The modified multipole shifting algorithm. , 2010, The Journal of chemical physics.

[22]  Maurice Leslie,et al.  DL_MULTI—A molecular dynamics program to use distributed multipole electrostatic models to simulate the dynamics of organic crystals , 2008 .

[23]  V. Hornak,et al.  Comparison of multiple Amber force fields and development of improved protein backbone parameters , 2006, Proteins.

[24]  David J. Wales,et al.  Topography of potential-energy surfaces for Van der Waals complexes , 1994 .

[25]  E. Spaeth.  Imidazole and its derivatives. Part I , 1954 .

[26]  Kazimierz Krynicki,et al.  Pressure and temperature dependence of self-diffusion in water , 1978 .

[27]  Michael D. Altman,et al.  Peptide self-assembly in functional polymer science and engineering , 1999 .

[28]  Paul L. A. Popelier,et al.  Integration of atoms in molecules: a critical examination , 1996 .

[29]  P. Popelier,et al.  Atomic properties of amino acids: computed atom types as a guide for future force-field design. , 2003, Chemphyschem : a European journal of chemical physics and physical chemistry.

[30]  J. Banavar,et al.  Computer Simulation of Liquids , 1988 .

[31]  Laurent Joubert,et al.  Convergence of the electrostatic interaction based on topological atoms , 2001 .

[32]  P. Popelier,et al.  Properties of liquid water from a systematic refinement of a high-rank multipolar electrostatic potential. , 2010, The Journal of chemical physics.

[33]  T. H. Dunning.  Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen , 1989 .

[34]  P. Popelier,et al.  The electrostatic potential generated by topological atoms. II. Inverse multipole moments. , 2005, The Journal of chemical physics.

[35]  William L. Jorgensen,et al.  Development of an All-Atom Force Field for Heterocycles. Properties of Liquid Pyrrole, Furan, Diazoles, and Oxazoles , 1998 .

[36]  B. Winter,et al.  Ionization of imidazole in the gas phase, microhydrated environments, and in aqueous solution. , 2008, The journal of physical chemistry. A.

[37]  Anthony J. Stone,et al.  Distributed multipole analysis, or how to describe a molecular charge distribution , 1981 .

[38]  Hsian-Rong Tseng,et al.  Chemical synthesis gets a fillip from molecular recognition and self-assembly processes , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[39]  R. Bader.  Atoms in molecules : a quantum theory , 1990 .

[40]  D. Lawrence,et al.  Self-Assembling Supramolecular Complexes , 1995 .

[41]  A. McDermott,et al.  Solid-State 15N NMR Chemical Shift Anisotropy of Histidines: Experimental and Theoretical Studies of Hydrogen Bonding† , 1999 .

[42]  P. Popelier,et al.  Simulation of liquid imidazole using a high-rank quantum topological electrostatic potential. , 2010, Physical chemistry chemical physics : PCCP.

[43]  J. Schnur,et al.  Lipid Tubules: A Paradigm for Molecularly Engineered Structures , 1993, Science.

[44]  Uwe Koch,et al.  Conformational dependence of atomic multipole moments , 1995 .

[45]  M. Panhuis,et al.  Distributed polarizability of the water dimer: Field-induced charge transfer along the hydrogen bond , 2001 .

[46]  F. Peral,et al.  Self-association of imidazole and its methyl derivatives in aqueous solution. A study by ultraviolet spectroscopy , 1997 .

[47]  Paul L. A. Popelier,et al.  Atom–atom partitioning of intramolecular and intermolecular Coulomb energy , 2001 .

[48]  T. Darden,et al.  Particle mesh Ewald: An N⋅log(N) method for Ewald sums in large systems , 1993 .

[49]  P. Popelier.  Quantum Chemical Topology: Bonds and Potentials , 2005 .

[50]  Paul L. A. Popelier,et al.  FORMULAS FOR THE 1ST AND 2ND DERIVATIVES OF ANISOTROPIC POTENTIALS WITH RESPECT TO GEOMETRICAL PARAMETERS , 1994 .

[51]  Paul L. A. Popelier,et al.  A ROBUST ALGORITHM TO LOCATE AUTOMATICALLY ALL TYPES OF CRITICAL-POINTS IN THE CHARGE-DENSITY AND ITS LAPLACIAN , 1994 .