Energy decomposition analysis of cation–π, metal ion–lone pair, hydrogen bonded, charge‐assisted hydrogen bonded, and π–π interactions

This study probes the nature of noncovalent interactions, such as cation–π, metal ion–lone pair (M–LP), hydrogen bonding (HB), charge‐assisted hydrogen bonding (CAHB), and π–π interactions, using energy decomposition schemes—density functional theory (DFT)–symmetry‐adapted perturbation theory and reduced variational space. Among cation–π complexes, the polarization and electrostatic components are the major contributors to the interaction energy (IE) for metal ion–π complexes, while for onium ion–π complexes ( NH4+ , PH4+ , OH3+ , and SH3+ ) the dispersion component is prominent. For M–LP complexes, the electrostatic component contributes more to the IE except the dicationic metal ion complexes with H2S and PH3 where the polarization component dominates. Although electrostatic component dominates for the HB and CAHB complexes, dispersion is predominant in π–π complexes.Copyright © 2015 Wiley Periodicals, Inc.

[1]  Pradeep Risikrishna Varadwaj,et al.  Hydrogen bonding interactions in PN···HX complexes: DFT and ab initio studies of structure, properties and topology , 2010, Journal of molecular modeling.

[2]  William H. Fink,et al.  Frozen fragment reduced variational space analysis of hydrogen bonding interactions. Application to the water dimer , 1987 .

[3]  Robert Moszynski,et al.  Perturbation Theory Approach to Intermolecular Potential Energy Surfaces of van der Waals Complexes , 1994 .

[4]  C. Chabalowski,et al.  Using Kohn−Sham Orbitals in Symmetry-Adapted Perturbation Theory to Investigate Intermolecular Interactions , 2001 .

[5]  David D Jenkins,et al.  STAAR: Statistical analysis of aromatic rings , 2013, J. Comput. Chem..

[6]  Georg Jansen,et al.  Intermolecular dispersion energies from time-dependent density functional theory , 2003 .

[7]  Valerio Bertolasi,et al.  The nature of solid-state N-H triplebondO/O-H triplebond N tautomeric competition in resonant systems. Intramolecular proton transfer in low-barrier hydrogen bonds formed by the triplebond O=C-C=N-NH triple bond --> <-- triplebond HO-C=C-N=N triplebond Ketohydrazone-Azoenol system. A variable-temper , 2002, Journal of the American Chemical Society.

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

[9]  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.

[10]  Hendrik Zipse,et al.  Explicit solvent effect on cation-pi interactions: a first principle investigation. , 2009, The journal of physical chemistry. B.

[11]  Hendrik Zipse,et al.  On the cooperativity of cation-pi and hydrogen bonding interactions. , 2008, The journal of physical chemistry. B.

[12]  C. David Sherrill,et al.  High-Accuracy Quantum Mechanical Studies of π−π Interactions in Benzene Dimers , 2006 .

[13]  Jiali Gao,et al.  Cation−π Interactions: An Energy Decomposition Analysis and Its Implication in δ-Opioid Receptor−Ligand Binding , 2002 .

[14]  K. Kitaura,et al.  Cl–π interactions in protein–ligand complexes , 2008, Protein science : a publication of the Protein Society.

[15]  John Frederick Beck,et al.  How resonance assists hydrogen bonding interactions: An energy decomposition analysis , 2007, J. Comput. Chem..

[16]  M. Schütz,et al.  Density-functional theory-symmetry-adapted intermolecular perturbation theory with density fitting: a new efficient method to study intermolecular interaction energies. , 2005, The Journal of chemical physics.

[17]  Krzysztof Szalewicz,et al.  Symmetry-adapted perturbation-theory calculations of intermolecular forces employing density-functional description of monomers. , 2005, The Journal of chemical physics.

[18]  Dongwook Kim,et al.  Cation-pi-anion interaction: a theoretical investigation of the role of induction energies. , 2007, The journal of physical chemistry. A.

[19]  G Narahari Sastry,et al.  Hydrogen bonding in water clusters and their ionized counterparts. , 2010, The journal of physical chemistry. B.

[20]  B. Mishra,et al.  Tuning the C-H···π Interaction by Different Substitutions in Benzene-Acetylene Complexes. , 2012, Journal of chemical theory and computation.

[21]  R. Leeuwen,et al.  Exchange-correlation potential with correct asymptotic behavior. , 1994, Physical review. A, Atomic, molecular, and optical physics.

[22]  Y. Mo,et al.  Energy decomposition analysis of intermolecular interactions using a block-localized wave function approach , 2000 .

[23]  Professor Dr. George A. Jeffrey,et al.  Hydrogen Bonding in Biological Structures , 1991, Springer Berlin Heidelberg.

[24]  Georg Jansen,et al.  How accurate is the density functional theory combined with symmetry-adapted perturbation theory approach for CH-pi and pi-pi interactions? A comparison to supermolecular calculations for the acetylene-benzene dimer. , 2007, Physical chemistry chemical physics : PCCP.

[25]  G. Chałasiński,et al.  State of the Art and Challenges of the ab Initio Theory of Intermolecular Interactions. , 2000, Chemical reviews.

[26]  Georg Jansen,et al.  Symmetry‐adapted perturbation theory based on density functional theory for noncovalent interactions , 2014 .

[27]  G Narahari Sastry,et al.  A theoretical study on interaction of cyclopentadienyl ligand with alkali and alkaline earth metals. , 2011, The journal of physical chemistry. B.

[28]  Georg Jansen,et al.  Intermolecular induction and exchange-induction energies from coupled-perturbed Kohn–Sham density functional theory , 2002 .

[29]  Tatiana Korona,et al.  A coupled cluster treatment of intramonomer electron correlation within symmetry-adapted perturbation theory: benchmark calculations and a comparison with a density-functional theory description , 2013 .

[30]  Jan Řezáč,et al.  Extrapolation and Scaling of the DFT-SAPT Interaction Energies toward the Basis Set Limit. , 2011, Journal of chemical theory and computation.

[31]  Swati Panigrahi,et al.  Noncovalent interaction of carbon nanostructures. , 2014, Accounts of chemical research.

[32]  Edward G Hohenstein,et al.  Density fitting of intramonomer correlation effects in symmetry-adapted perturbation theory. , 2010, The Journal of chemical physics.

[33]  Valerio Bertolasi,et al.  Evidence for Intramolecular N−H···O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation , 2000 .

[34]  Dolly Vijay,et al.  The impact of basis set superposition error on the structure of ππ dimers , 2011 .

[35]  Dolly Vijay,et al.  The significance of the alkene size and the nature of the metal ion in metal-alkene complexes: a theoretical study. , 2012, Dalton transactions.

[36]  Jiali Gao,et al.  Energy decomposition analysis based on a block-localized wavefunction and multistate density functional theory. , 2011, Physical chemistry chemical physics : PCCP.

[37]  Thomas R. Cundari,et al.  Reduced variational space analysis of methane adducts , 1998 .

[38]  Pavel Hobza,et al.  Strength and Character of Halogen Bonds in Protein–Ligand Complexes , 2011 .

[39]  J. V. Lenthe,et al.  State of the Art in Counterpoise Theory , 1994 .

[40]  J. Israelachvili.  Intermolecular and surface forces , 1985 .

[41]  Nohad Gresh,et al.  Design Of Next Generation Force Fields From AB Initio Computations: Beyond Point Charges Electrostatics , 2009 .

[42]  Steve Scheiner,et al.  A new noncovalent force: comparison of P···N interaction with hydrogen and halogen bonds. , 2011, The Journal of chemical physics.

[43]  Jiali Gao,et al.  Polarization and charge-transfer effects in aqueous solution via ab initio QM/MM simulations. , 2006, The journal of physical chemistry. B.

[44]  Mark S. Gordon,et al.  Energy Decomposition Analyses for Many-Body Interaction and Applications to Water Complexes , 1996 .

[45]  R. Podeszwa,et al.  Density-Fitting Method in Symmetry-Adapted Perturbation Theory Based on Kohn-Sham Description of Monomers , 2006, 2006 HPCMP Users Group Conference (HPCMP-UGC'06).

[46]  R. Parthasarathi,et al.  Hydrogen bonding without borders: an atoms-in-molecules perspective. , 2006, The journal of physical chemistry. A.

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

[48]  G Narahari Sastry,et al.  Ab initio investigation of benzene clusters: molecular tailoring approach. , 2010, The Journal of chemical physics.

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

[50]  G. N. Sastry,et al.  Aromatic-Aromatic Interactions Database, A(2)ID: an analysis of aromatic π-networks in proteins. , 2011, International journal of biological macromolecules.

[51]  Peter Pulay,et al.  High accuracy benchmark calculations on the benzene dimer potential energy surface , 2007 .

[52]  Pavel Hobza,et al.  Highly accurate CCSD(T) and DFT-SAPT stabilization energies of H-bonded and stacked structures of the uracil dimer. , 2008, Chemphyschem : a European journal of chemical physics and physical chemistry.

[53]  Georg Jansen,et al.  First-order intermolecular interaction energies from Kohn–Sham orbitals , 2002 .

[54]  G Narahari Sastry,et al.  Cation–aromatic database , 2007, Proteins.

[55]  Sanjay Wategaonkar,et al.  Sulfur, not too far behind O, N, and C: SH...pi hydrogen bond. , 2009, The journal of physical chemistry. A.

[56]  Mark S. Gordon,et al.  General atomic and molecular electronic structure system , 1993, J. Comput. Chem..

[57]  Shridhar R. Gadre,et al.  Electrostatics of Atoms and Molecules , 2001 .

[58]  Marcos Mandado,et al.  Electron Density Based Partitioning Scheme of Interaction Energies. , 2011, Journal of chemical theory and computation.

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

[60]  Pavel Hobza,et al.  On the nature of stabilization in weak, medium, and strong charge-transfer complexes: CCSD(T)/CBS and SAPT calculations. , 2011, The journal of physical chemistry. A.

[61]  Pavel Hobza,et al.  On the nature of the stabilization of benzene···dihalogen and benzene···dinitrogen complexes: CCSD(T)/CBS and DFT-SAPT calculations. , 2011, Chemphyschem : a European journal of chemical physics and physical chemistry.

[62]  Dolly Vijay,et al.  Exploring the size dependence of cyclic and acyclic pi-systems on cation-pi binding. , 2008, Physical chemistry chemical physics : PCCP.

[63]  Dolly Vijay,et al.  The cooperativity of cation–π and π–π interactions , 2010 .

[64]  G. N. Sastry,et al.  Cation-π interaction: its role and relevance in chemistry, biology, and material science. , 2013, Chemical reviews.

[65]  Bhaskar Sharma,et al.  Contrasting preferences of N and P substituted heteroaromatics towards metal binding: probing the regioselectivity of Li+ and Mg2+ binding to (CH)(6-m-n)N(m)P(n). , 2012, Physical chemistry chemical physics : PCCP.

[66]  Krzysztof Szalewicz,et al.  Symmetry‐adapted perturbation theory of intermolecular forces , 2012 .

[67]  Kwang Soo Kim,et al.  Molecular Clusters of pi-Systems: Theoretical Studies of Structures, Spectra, and Origin of Interaction Energies. , 2000, Chemical reviews.

[68]  Hui Li,et al.  Energy decomposition analysis of covalent bonds and intermolecular interactions. , 2009, The Journal of chemical physics.

[69]  Yuchun Lin,et al.  Block-localized wavefunction (BLW) method at the density functional theory (DFT) level. , 2007, The journal of physical chemistry. A.

[70]  S. J. Grabowski,et al.  Hydrogen Bonding—New Insights , 2006 .

[71]  Mehdi D. Esrafili,et al.  How do phosphoramides compete with phosphine oxides in lanthanide complexation? Structural, electronic and energy aspects at ab initio and DFT levels , 2010 .

[72]  Sarah L Price,et al.  Accurate Induction Energies for Small Organic Molecules. 2. Development and Testing of Distributed Polarizability Models against SAPT(DFT) Energies. , 2008, Journal of chemical theory and computation.

[73]  Elizabeth E Howell,et al.  A survey of aspartate-phenylalanine and glutamate-phenylalanine interactions in the protein data bank: searching for anion-π pairs. , 2011, Biochemistry.

[74]  Kazuo Kitaura,et al.  A new energy decomposition scheme for molecular interactions within the Hartree‐Fock approximation , 1976 .

[75]  Krzysztof Szalewicz,et al.  Efficient calculation of coupled Kohn-Sham dynamic susceptibility functions and dispersion energies with density fitting , 2005 .

[76]  Henry Margenau,et al.  Theory of intermolecular forces , 1969 .

[77]  E. Jemmis,et al.  Red-, blue-, or no-shift in hydrogen bonds: a unified explanation. , 2007, Journal of the American Chemical Society.

[78]  Pavel Hobza,et al.  Noncovalent interactions in biochemistry , 2011 .

[79]  Valerio Bertolasi,et al.  The Nature of Solid-State N−H···O/O−H···N Tautomeric Competition in Resonant Systems. Intramolecular Proton Transfer in Low-Barrier Hydrogen Bonds Formed by the ···OC−CN−NH··· ⇄ ···HO−CC−NN··· Ketohydrazone−Azoenol System. A Variable-Temperature X-ray Crystallographic and DFT Computational Study , 2002 .

[80]  C. David Sherrill,et al.  Substituent Effects in π−π Interactions: Sandwich and T-Shaped Configurations , 2004 .

[81]  Eric D. Glendening,et al.  Natural energy decomposition analysis: An energy partitioning procedure for molecular interactions with application to weak hydrogen bonding, strong ionic, and moderate donor–acceptor interactions , 1994 .

[82]  Anthony J Stone,et al.  Accurate Induction Energies for Small Organic Molecules:  1. Theory. , 2008, Journal of chemical theory and computation.

[83]  Clemence Corminboeuf,et al.  Dispersion-corrected energy decomposition analysis for intermolecular interactions based on the BLW and dDXDM methods. , 2011, The journal of physical chemistry. A.

[84]  Pavel Hobza,et al.  Assessment of the MP2 method, along with several basis sets, for the computation of interaction energies of biologically relevant hydrogen bonded and dispersion bound complexes. , 2007, The journal of physical chemistry. A.

[85]  Georg Jansen,et al.  The helium dimer potential from a combined density functional theory and symmetry-adapted perturbation theory approach using an exact exchange–correlation potential , 2003 .

[86]  Ilya G. Kaplan,et al.  Intermolecular interactions : physical picture, computational methods, model potentials , 2006 .