Halogen-Bonding Interactions with π Systems: CCSD(T), MP2, and DFT Calculations

被引:55
作者
Forni, Alessandra [1 ,3 ]
Pieraccini, Stefano [1 ,2 ,3 ]
Rendine, Stefano [2 ,3 ]
Gabas, Fabio [2 ,3 ]
Sironi, Maurizio [1 ,2 ,3 ]
机构
[1] CNR, ISTM, I-20133 Milan, Italy
[2] Univ Milan, Dipartimento Chim, I-20133 Milan, Italy
[3] Univ Milan, INSTM UdR, I-20133 Milan, Italy
关键词
halogens; noncovalent interactions; pi interactions; density functional calculations; computational chemistry; DENSITY-FUNCTIONAL THERMOCHEMISTRY; AB-INITIO; CHARGE-DENSITY; MOLECULAR-INTERACTIONS; CRYSTAL-STRUCTURES; BENZENE COMPLEXES; ENERGY; INSIGHTS; WEAK; CONFORMATION;
D O I
10.1002/cphc.201200605
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Halogen bonding is a noncovalent interaction between a halogen atom and a nucleophilic site. Interactions involving the p 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 Moller-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.
引用
收藏
页码:4224 / 4234
页数:11
相关论文
共 91 条
[21]   Is Organic Fluorine Really "Not" Polarizable? [J].
Chopra, Deepak .
CRYSTAL GROWTH & DESIGN, 2012, 12 (02) :541-546
[22]   Topological analysis of aromatic halogen/hydrogen bonds by electron charge density and electrostatic potentials [J].
Duarte, Dario J. R. ;
de las Vallejos, Margarita M. ;
Peruchena, Nelida M. .
JOURNAL OF MOLECULAR MODELING, 2010, 16 (04) :737-748
[24]   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 [J].
Espinosa, E ;
Alkorta, I ;
Elguero, J ;
Molins, E .
JOURNAL OF CHEMICAL PHYSICS, 2002, 117 (12) :5529-5542
[25]   Solvent effect on halogen bonding: The case of the I. . .O interaction [J].
Forni, Alessandra ;
Rendine, Stefano ;
Pieraccini, Stefano ;
Sironi, Maurizio .
JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2012, 38 :31-39
[26]   Experimental and Theoretical Study of the Br•••N Halogen Bond in Complexes of 1,4-Dibromotetrafluorobenzene with Dipyridyl Derivatives [J].
Forni, Alessandra .
JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (14) :3403-3412
[27]   Activation of hydrogen- and halogen-bonding interactions in tetrathiafulvalene-based crystalline molecular conductors [J].
Fourmigué, M ;
Batail, P .
CHEMICAL REVIEWS, 2004, 104 (11) :5379-5418
[28]   A thorough benchmark of density functional methods for general main group thermochemistry, kinetics, and noncovalent interactions [J].
Goerigk, Lars ;
Grimme, Stefan .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (14) :6670-6688
[29]   Semiempirical GGA-type density functional constructed with a long-range dispersion correction [J].
Grimme, Stefan .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2006, 27 (15) :1787-1799
[30]   Basis set convergence of the interaction energy of hydrogen-bonded complexes [J].
Halkier, A ;
Klopper, W ;
Helgaker, T ;
Jorgensen, P ;
Taylor, PR .
JOURNAL OF CHEMICAL PHYSICS, 1999, 111 (20) :9157-9167