Halogen-bonding interactions with π systems: CCSD(T), MP2, and DFT calculations.

Halogen bonding is a noncovalent interaction between a halogen atom and a nucleophilic site. Interactions involving the π electrons of aromatic rings have received, up to now, little attention, despite the large number of systems in which they are present. We report binding energies of the interaction between either NCX or PhX (X = F, Cl, Br, I) and the aromatic benzene system as determined with the coupled cluster with perturbative triple excitations method [CCSD(T)] extrapolated at the complete basis set limit. Results are compared with those obtained by Møller-Plesset perturbation theory to second order (MP2) and density functional theory (DFT) calculations by using some of the most common functionals. Results show the important role of DFT in studying this interaction.

[1]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.

[2]  Hisayoshi Kobayashi,et al.  Diastereomers of dibromo-7-epi-10-deacetylcephalomannine: crowded and cytotoxic taxanes exhibit halogen bonds. , 2006, Journal of medicinal chemistry.

[3]  Timothy Clark,et al.  Halogen bonding: an electrostatically-driven highly directional noncovalent interaction. , 2010, Physical chemistry chemical physics : PCCP.

[4]  B. Shepler,et al.  On the spectroscopic and thermochemical properties of ClO, BrO, IO, and their anions. , 2006, The journal of physical chemistry. A.

[5]  Bin Ye,et al.  Crystal structures of two potent nonamidine inhibitors bound to factor Xa. , 2002, Biochemistry.

[6]  Claude Lecomte,et al.  The nature of halogen...halogen interactions: a model derived from experimental charge-density analysis. , 2009, Angewandte Chemie.

[7]  J. Zou,et al.  Substituent effects on noncovalent halogen/π interactions: Theoretical study , 2007 .

[8]  Xiang Zhu,et al.  How does halogen bonding behave in solution? A theoretical study using implicit solvation model. , 2011, The journal of physical chemistry. A.

[9]  J. Zou,et al.  Ab initio and atoms in molecules analyses of halogen bonding with a continuum of strength , 2006 .

[10]  Vincenzo Barone,et al.  Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters: The mPW and mPW1PW models , 1998 .

[11]  Kumar Biradha,et al.  Design of an SHG-active crystal, 4-iodo-4′-nitrobiphenyl: the role of supramolecular synthons , 1997 .

[12]  D. Truhlar,et al.  The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals , 2008 .

[13]  Stefan Güssregen,et al.  Evidence for C-Cl/C-Br...pi interactions as an important contribution to protein-ligand binding affinity. , 2009, Angewandte Chemie.

[14]  Stefan Grimme,et al.  Semiempirical GGA‐type density functional constructed with a long‐range dispersion correction , 2006, J. Comput. Chem..

[15]  Xiaoyan Li,et al.  Ab initio and AIM studies on typical π‐type and pseudo‐π‐type halogen bonds: Comparison with hydrogen bonds , 2011 .

[16]  S. Grimme,et al.  A thorough benchmark of density functional methods for general main group thermochemistry, kinetics, and noncovalent interactions. , 2011, Physical chemistry chemical physics : PCCP.

[17]  Michael B Hursthouse,et al.  Halogen bonding: a new interaction for liquid crystal formation. , 2004, Journal of the American Chemical Society.

[18]  K. Rissanen,et al.  Nonporous Organic Solids Capable of Dynamically Resolving Mixtures of Diiodoperfluoroalkanes , 2009, Science.

[19]  M. Nishio,et al.  The CH/π hydrogen bond in chemistry. Conformation, supramolecules, optical resolution and interactions involving carbohydrates. , 2011, Physical chemistry chemical physics : PCCP.

[20]  K. Rissanen,et al.  Dimensional encapsulation of I(-)...I(2)...I(-) in an organic salt crystal matrix. , 2010, Chemical communications.

[21]  Martin Head-Gordon,et al.  Quadratic configuration interaction. A general technique for determining electron correlation energies , 1987 .

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

[23]  S. Tsuzuki,et al.  Origin of attraction, magnitude, and directionality of interactions in benzene complexes with pyridinium cations. , 2007, Journal of the American Chemical Society.

[24]  M. Head‐Gordon,et al.  Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. , 2008, Physical chemistry chemical physics : PCCP.

[25]  K. Sekar,et al.  C-halogen…π interactions in proteins: a database study , 2003 .

[26]  Pierangelo Metrangolo,et al.  Tuning second-order NLO responses through halogen bonding. , 2007, Chemical communications.

[27]  Kangwon Lee,et al.  Activating efficient phosphorescence from purely organic materials by crystal design. , 2011, Nature chemistry.

[28]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[29]  P. Metrangolo,et al.  Halogen Versus Hydrogen , 2008, Science.

[30]  Pierangelo Metrangolo,et al.  Halogenbrücken in der supramolekularen Chemie , 2008 .

[31]  B. Sumpter,et al.  Density-functional approaches to noncovalent interactions: a comparison of dispersion corrections (DFT-D), exchange-hole dipole moment (XDM) theory, and specialized functionals. , 2011, The Journal of chemical physics.

[32]  William J. Welsh,et al.  Halogenated ligands and their interactions with amino acids: implications for structure-activity and structure-toxicity relationships. , 2008, Journal of molecular graphics & modelling.

[33]  Jianwei Xu,et al.  Trimeric supramolecular liquid crystals induced by halogen bonds , 2006 .

[34]  Burke,et al.  Generalized Gradient Approximation Made Simple. , 1996, Physical review letters.

[35]  Kevin E. Riley,et al.  Insights into the strength and origin of halogen bonding: the halobenzene-formaldehyde dimer. , 2007, The journal of physical chemistry. A.

[36]  Maurizio Sironi,et al.  Halogen bonding in ligand-receptor systems in the framework of classical force fields. , 2011, Physical chemistry chemical physics : PCCP.

[37]  P Shing Ho,et al.  Halogen bonds as orthogonal molecular interactions to hydrogen bonds. , 2009, Nature chemistry.

[38]  Pavel Hobza,et al.  Investigations into the Nature of Halogen Bonding Including Symmetry Adapted Perturbation Theory Analyses. , 2008, Journal of chemical theory and computation.

[39]  M. Nishio,et al.  interaction in the conformation of organic compounds. A database study , 1999 .

[40]  M. Head‐Gordon,et al.  Systematic optimization of long-range corrected hybrid density functionals. , 2008, The Journal of chemical physics.

[41]  Yong-Jun Jiang,et al.  Halogen Bonding: An AIM Analysis of the Weak Interactions , 2006 .

[42]  Pierangelo Metrangolo,et al.  Halogen bonding : fundamentals and applications , 2008 .

[43]  Jian-Wei Zou,et al.  Theoretical investigations of the C X/π interactions between benzene and some model halocarbons , 2007 .

[44]  A. Bondi.  van der Waals Volumes and Radii , 1964 .

[45]  A. W. Hanson.  The crystal structure of the 1:1 complexes of skatole and indole with s‐trinitrobenzene , 1964 .

[46]  Maurizio Sironi,et al.  Solvent effect on halogen bonding: the case of the I⋯O interaction. , 2012, Journal of molecular graphics & modelling.

[47]  E. Molins,et al.  From weak to strong interactions: A comprehensive analysis of the topological and energetic properties of the electron density distribution involving X–H⋯F–Y systems , 2002 .

[48]  S. F. Boys,et al.  The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors , 1970 .

[49]  Trygve Helgaker,et al.  Basis set convergence of the interaction energy of hydrogen-bonded complexes , 1999 .

[50]  Xiang Zhu,et al.  Interplay between halogen bonds and π-π stacking interactions: CSD search and theoretical study. , 2012, Physical chemistry chemical physics : PCCP.

[51]  Axel D. Becke,et al.  Optimized density functionals from the extended G2 test set , 1998 .

[52]  A. Becke.  Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals , 1997 .

[53]  Pavel Hobza,et al.  Stabilization and structure calculations for noncovalent interactions in extended molecular systems based on wave function and density functional theories. , 2010, Chemical reviews.

[54]  François Diederich,et al.  Systematic investigation of halogen bonding in protein-ligand interactions. , 2011, Angewandte Chemie.

[55]  C David Sherrill,et al.  An Assessment of Density Functional Methods for Potential Energy Curves of Nonbonded Interactions: The XYG3 and B97-D Approximations. , 2010, Journal of chemical theory and computation.

[56]  Uwe Koch,et al.  CHARACTERIZATION OF C-H-O HYDROGEN-BONDS ON THE BASIS OF THE CHARGE-DENSITY , 1995 .

[57]  Pierangelo Metrangolo,et al.  Halogen bonding in supramolecular chemistry. , 2008, Angewandte Chemie.

[58]  Oleg V. Shishkin,et al.  Evaluation of true energy of halogen bonding in the crystals of halogen derivatives of trityl alcohol , 2008 .

[59]  A. Forni.  Experimental and theoretical study of the Br...N halogen bond in complexes of 1,4-dibromotetrafluorobenzene with dipyridyl derivatives. , 2009, The journal of physical chemistry. A.

[60]  A. Whitwood,et al.  Structure-function relationships in liquid-crystalline halogen-bonded complexes. , 2010, Chemistry.

[61]  Nélida M. Peruchena,et al.  Topological analysis of aromatic halogen/hydrogen bonds by electron charge density and electrostatic potentials , 2010, Journal of molecular modeling.

[62]  Deepak Chopra,et al.  Is Organic Fluorine Really “Not” Polarizable? , 2012 .

[63]  M. W. Wong,et al.  Saturated hydrocarbon-benzene complexes: theoretical study of cooperative CH/pi interactions. , 2006, The journal of physical chemistry. A.

[64]  M. Bhadbhade,et al.  Halogen Bonding in 2,5-Dichloro-1,4-benzoquinone: Insights from Experimental and Theoretical Charge Density Analysis , 2011 .

[65]  Klaus R Liedl,et al.  Dispersion dominated halogen-π interactions: energies and locations of minima. , 2010, Physical chemistry chemical physics : PCCP.

[66]  Edward F. Valeev,et al.  Estimates of the Ab Initio Limit for π−π Interactions: The Benzene Dimer , 2002 .

[67]  W. J. Orville-Thomas.  Atoms in Molecules — a Quantum Theory , 1996 .

[68]  Weiliang Zhu,et al.  Halogen bonding--a novel interaction for rational drug design? , 2009, Journal of medicinal chemistry.

[69]  Eric Westhof,et al.  Halogen bonds in biological molecules. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[70]  Seiji Tsuzuki,et al.  CH/π interactions , 2012 .

[71]  Lippmann,et al.  Topological analyses of cuprite, Cu2O, using high-energy synchrotron-radiation data , 2000, Acta crystallographica. Section A, Foundations of crystallography.

[72]  Peter Politzer,et al.  An overview of halogen bonding , 2007, Journal of molecular modeling.

[73]  Gautam R Desiraju,et al.  1,3-Dibromo-2,4,6-trinitrobenzene (DBTNB). Crystal engineering and perfect polar alignment of two-dimensional hyperpolarizable chromophores. , 2002, Chemical communications.

[74]  Marc Fourmigué,et al.  Activation of hydrogen- and halogen-bonding interactions in tetrathiafulvalene-based crystalline molecular conductors. , 2004, Chemical reviews.

[75]  Hanno Essén,et al.  The characterization of atomic interactions , 1984 .

[76]  Yong-Jun Jiang,et al.  Ab initio calculations on halogen‐bonded complexes and comparison with density functional methods , 2009, J. Comput. Chem..

[77]  Marcelo Zaldini Hernandes,et al.  Halogen atoms in the modern medicinal chemistry: hints for the drug design. , 2010, Current drug targets.

[78]  Pavel Hobza,et al.  Br···O Complexes as Probes of Factors Affecting Halogen Bonding: Interactions of Bromobenzenes and Bromopyrimidines with Acetone. , 2009, Journal of chemical theory and computation.

[79]  Xiang Zhu,et al.  Effects of solvent on weak halogen bonds: Density functional theory calculations , 2012 .

[80]  Yong-Jun Jiang,et al.  Ab initio investigation of the complexes between bromobenzene and several electron donors: some insights into the magnitude and nature of halogen bonding interactions. , 2007, The journal of physical chemistry. A.

[81]  N. Peruchena,et al.  Halogen bonding: a study based on the electronic charge density. , 2010, The journal of physical chemistry. A.

[82]  Jianwei Xu,et al.  Synthesis and Self-Assembly of Difunctional Halogen-Bonding Molecules: A New Family of Supramolecular Liquid-Crystalline Polymers , 2005 .

[83]  Hiroshi Yamamoto,et al.  An application of supramolecular chemistry to molecular conductors , 2002 .

[84]  R E Cachau,et al.  Ultrahigh resolution drug design I: Details of interactions in human aldose reductase–inhibitor complex at 0.66 Å , 2004, Proteins.

[85]  Lori A Burns,et al.  Assessment of the Performance of DFT and DFT-D Methods for Describing Distance Dependence of Hydrogen-Bonded Interactions. , 2011, Journal of chemical theory and computation.

[86]  D. Banner,et al.  Systematische Untersuchung von Halogenbrücken in Protein‐Ligand‐ Wechselwirkungen , 2011 .

[87]  P. J. Langley,et al.  On intrinsic and extrinsic defect-forming mechanisms determining the disordered structure of 4-iodo-4′-nitrobiphenyl crystals , 1998 .