Structures of protonated benzene dimer and intermolecular interaction decomposition via symmetry-adapted perturbation theory

Computational and Theoretical Chemistry

Volumn 973, Issue 1-3, 2011, Pages 47-52

  Jaeger, Heather M ^a   Schaefer, Henry F ^a   Hohenstein, Edward G ^b   David Sherrill, C ^b  

^a UNIVERSITY OF GEORGIA   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Benzene dimer; Benzenium; Intermolecular interactions; Protonated benzene; SAPT

Indexed keywords

EID: 84855180370     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2011.06.027     Document Type: Article

References (44)

1. Meyer E.A., Castellano R.K., Diederich F. Interactions with aromatic rings in chemical and biological recognition. Angew. Chem. Int. Ed. 2003, 42:1210-1250.
2. Kim K.S., Tarakeshwar P., Lee J.Y. Molecular clusters of π-systems: theoretical studies of structures, spectra, and origin of interaction energies. Chem. Rev. 2000, 100:4145-4186.
3. Dougherty D.A. Cation-π interactions in chemistry and biology: a new view of benzene, Phe, Tyr, and Trp. Science 1996, 271:163-168.
4. Mecozzi S., West A.P., Dougherty D.A. Cation-π interactions in simple aromatics: electrostatics provide a predictive tool. J. Am. Chem. Soc. 1996, 118:2307-2308.
5. Ma J.C., Dougherty D.A. The cation-π interaction. Chem. Rev. 1997, 97:1303-1324.
6. Tsuzuki S., Yoshida M., Uchimaru T., Mikami M. The origin of the cation/π interaction: the significant importance of the induction in Li+ and Na+ complexes. J. Phys. Chem. A 2001, 105:769-773.
7. Tsou L.K., Tatko C.D., Waters M.L. Simple cation-π interaction between an phenyl ring and a protonated amine stabilizes an α-helix in water. J. Am. Chem. Soc. 2002, 124:14917-14921.
8. Kim D., Hu S., Tarakeshwar P., Kim K.S., Lisy J.M. Cation-π interactions: a theoretical investigation of the interaction of metallic and organic cations with alkenes, arenes, and heteroarenes. J. Phys. Chem. A 2003, 107:1228-1238.
9. Dinadayalane T.C., Afanasiev D., Leszczynski J. Structures and energetics of the cation-π interactions of Li+, Na+, and K+ with cup-shaped molecules: effect of ring addition to benzene and cavity selectivity. J. Phys. Chem. A 2008, 112:7916-7924.
10. Dölker N., Deupi X., Pardo L., Campillo M. Charge-charge and cation-π interactions in ligand binding to G protein-coupled receptors. Theor. Chem. Acc. 2007, 118:579-588.
11. Vacas T., Corzana F., Jiménez-Osés G., González C., Gómez A.M., Bastida A., Revuelta J., Asensio J.L. Role of aromatic rings in the molecular recognition of aminoglycoside antibiotics: implications for drug design. J. Am. Chem. Soc. 2010, 132:12074-12090.
12. Xiu X., Puskar N.L., Shanata J.A.P., Lester H.A., Dougherty D.A. Nicotine binding to brain receptors requires a strong cation-π interaction. Nature 2009, 458:534-537.
13. Tsuzuki S., Fujii A. Nature and physical origin of CH/π interaction: significant difference from conventional hydrogen bonds. Phys. Chem. Chem. Phys. 2008, 10:2584-2594.
14. Grimme S. Do special noncovalent π-π stacking interactions really exist?. Angew. Chem. Int. Ed. 2008, 47:3430-3434.
15. Olah G.A., Schlosberg R.H., Kelly D.P., Mateescu G.D. Stable carbonium ions. IC. benzenonium ion (C6H7+) and its degenerate rearrangement. J. Am. Chem. Soc. 1970, 92:2546-2548.
16. Olah G.A., Schlosberg R.H., Porter R.D., Mo Y.K., Kelly D.P., Mateescu G.D. Stable carbocations. CXXIV. Benzenium ion and monoalkylbenzenium ions. J. Am. Chem. Soc. 1972, 94:2034-2043.
17. Olah G.A., Staral J.S., Asencio G., Liang G., Forsyth D.A., Mateescu G.D. Stable carbocations. 215. Carbon-13 nuclear magnetic resonance spectroscopic study of the benzenium, naphthalenium, and anthracenium ions. J. Am. Chem. Soc. 1978, 100:6299-6308.
18. Perkampus H.H., Baumgarten E. Proton-addition complexes of aromatic hydrocarbons. Angew. Chem. Int. Ed. 1964, 3:776-783.
19. Buckingham A.D., Del Bene J.E., McDowell S.A.C. The hydrogen bond. Chem. Phys. Lett. 2008, 463:1-10.
20. Karlstroem G., Linse P., Wallqvist A., Joensson B. Intermolecular potentials for the water-benzene and the benzene-benzene systems calculated in an ab initio SCFCI approximation. J. Am. Chem. Soc. 1983, 105:3777-3782.
21. Hobza P., Selzle H.L., Schlag E.W. Structure and properties of benzene-containing molecular clusters: nonempirical ab initio calculations and experiments. Chem. Rev. 1994, 94:1767-1785.
22. Tsuzuki S., Honda K., Uchimaru T., Mikami M., Tanabe K. Origin of attraction and directionality of the π/π interaction: model chemistry calculations of benzene dimer interaction. J. Am. Chem. Soc. 2002, 124:104-112.
23. Sinnokrot M.O., Sherrill C.D. High-accuracy quantum mechanical studies of π-π interactions in benzene dimers. J. Phys. Chem. A 2006, 110:10656-10668.
24. Park Y.C., Lee J.S. Accurate ab initio binding energies of the benzene dimer. J. Phys. Chem. A 2006, 110:5091-5095.
25. 2S. J. Phys. Chem. A 2009, 113:10146-10159.
26. DiStasio R.A., von Helden G., Steele R.P., Head-Gordon M. On the T-shaped structures of the benzene dimer. Chem. Phys. Lett. 2007, 437:277-283.
27. Podeszwa R., Bukowski R., Szalewicz K. Potential energy surface for the benzene dimer and perturbational analysis of π-π interactions. J. Phys. Chem. A 2006, 110:10345-10354.
28. Chakraborty S., Omidyan R., Alata I., Nielsen I.B., Dedonder C., Broquier M., Jouvet C. Protonated benzene dimer: an experimental and ab initio study. J. Am. Chem. Soc. 2009, 131:11091-11097.
29. Jaziorski B., Moszynski R., Szalewicz K. Perturbation theory approach to intermolecular potential energy surfaces of van der Waals complexes. Chem. Rev. 1994, 94:1887-1930.
30. Colven M.E., Janssen C.L., Whiteside R.A., Tong C.H. Parallel direct SCF for large-scale calculations. Theor. Chim. Acta 1993, 84:301-314.
31. R.D. Amos, A. Bernhardsson, A. Berning, P. Celani, D.L. Cooper, M.J.O. Deegan, A.J. Dobbyn, F. Eckert, C. Hampel, G. Hetzer, P.J. Knowles, T. Korona, R. Lindh, A.W. Lloyd, S.J. McNicholas, F.R. Manby, W. Meyer, M.E. Mura, A. Nicklass, P. Palmieri, R. Pitzer, G. Rauhut, M. Schütz, U. Schumann, H. Stoll, A.J. Stone, R. Tarroni, T. Thorsteinsson, H.J. Werner, MOLPRO, A Package of ab initio Programs Designed by H.-J. Werner, P.J. Knowles, version 2006.1.
32. Woon D.E., Dunning T.H. Gaussian basis sets for use in correlated molecular calculations. III. The atoms aluminum through argon. J. Chem. Phys. 1993, 98:1358-1371.
33. Kendall R.A., Dunning T.H., Harrison R.J. Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions. J. Chem. Phys. 1992, 96:6796-6806.
34. Boys S.F., Bernardi F. The calculation of small molecular interaction by the differences of separate total energies: some procedures with reduced errors. Mol. Phys. 1970, 19:553-566.
35. Jeziorski B., Moszynski R., Ratkiewicz S., Rybak K., Szalewicz K., Williams H.L. Volume B (medium-size systems). Methods and Techniques in Computational Chemistry: METECC94 1993, 79-85. STEF, Cagliari. E. Clementi (Ed.).
36. Hohenstein E.G., Sherrill C.D. Density fitting of intramonomer correlation effects in symmetry-adapted perturbation theory. J. Chem. Phys. 2010, 133:014101-1-014101-12.
37. Crawford T.D., Sherrill C.D., Valeev E.F., Fermann J.T., King R.A., Leininger M.L., Brown S.T., Janssen C.L., Seidl E.T., Kenny J.P., Allen W.D. PSI3: an open-source ab initio electronic structure package. J. Comput. Chem. 2007, 28:1610-1616.
38. Hohenstein E.G., Sherrill C.D. Density fitting and Cholesky decomposition approximations in symmetry-adapted perturbation theory: implementation and application to probe the nature of π-π interactions in linear acenes. J. Chem. Phys. 2010, 132:184111-1-184111-10.
39. Hohenstein E.G., Sherrill C.D. Efficient evaluation of triple excitations in symmetry-adapted perturbation theory via second-order Møller-Plesset perturbation theory natural orbitals. J. Chem. Phys. 2010, 133:104107-1-104107-7.
40. Marshall M.S., Steele R.P., Thanthiriwatte K.S., Sherrill C.D. Potential energy curves for cation-π interactions: off-axis configurations are also attractive. J. Phys. Chem. A 2009, 113:13628-13632.
41. δ+...X. Complexes of quaternary ions with n- and π-donors. J. Am. Chem. Soc. 1985, 107:469-474.
42. Pieniazek P.A., Bradforth S.E., Krylov A.I. Charge localization and Jahn-Teller distortions in the benzene dimer cation. J. Chem. Phys. 2008, 129:074104-1-074104-11.
43. Hopkins B.W., Tschumper G.S. Ab initio studies of π···π interactions: the effects of quadruple excitations. J. Phys. Chem. A 2004, 108:2941-2948.
44. Schwabe T., Grimme S. Benzenium-ethene complex: a fundamental problem for standard second-order Møller-Plesset theory. J. Phys. Chem. A 2009, 113:3005-3008.