A theoretical study of N-H ⋯ π H-bond interaction of pyrrole: From clusters to the liquid

Molecular Physics

Volumn 110, Issue 18, 2012, Pages 2151-2161

  Gao, Wei ^a,b   Feng, Huajie ^a   Xuan, Xiaopeng ^c   Chen, Liuping ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b GUANGDONG PHARMACEUTICAL UNIVERSITY   (China)

^c HENAN NORMAL UNIVERSITY   (China)

Author keywords

liquid pyrrole; N H H bond; pyrrole cluster; QM and MD

Indexed keywords

AIM ANALYSIS; ATOMS IN MOLECULES; CLASSICAL MOLECULAR DYNAMICS; DISPERSION CORRECTION; DONOR-ACCEPTOR ORBITALS; ENERGY DECOMPOSITION ANALYSIS; LIQUID PYRROLE; MD SIMULATION; NATURAL BOND ORBITAL; OPTIMIZED GEOMETRIES; PURE LIQUIDS; PYRROLE CLUSTER; THEORETICAL STUDY;

AROMATIC COMPOUNDS; DISPERSIONS; MOLECULAR DYNAMICS; OPTIMIZATION; QUANTUM THEORY;

LIQUIDS;

EID: 84867049978     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/00268976.2012.666277     Document Type: Article

References (69)

1. G. Columberg and A. Bauder, J. Chem. Phys. 106, 504 (1997).
2. H. Park and S. Lee, Chem. Phys. Lett. 301, 487 (1999).
3. V. Lukeš,M. Breza and S. Biskupič, Theor. Chem. Acct. 101, 319 (1999).
4. V. Stefov, L. Pejov and B. Šoptrajanov, J. Mol. Struct. 651-653, 793 (2003).
5. A. Gömez-Zavaglia and R. Fausto, J. Phys. Chem. A 108, 6953 (2004).
6. Y. Matsumotoa and K. Honma, J. Chem. Phys. 127, 184310 (2007).
7. S. Sun, H. Tang and P. Wu, Phys. Chem. Chem. Phys. 11, 7611 (2009).
8. I. Dauster, C.A. Rice, P. Zielke and M.A. Suhm, Phys. Chem. Chem. Phys. 10, 2827 (2008).
9. V. Profant, V. Poterya and M. Fárni'k, J. Phys. Chem. A 111, 12477 (2007).
10. L. Gontrani, F. Ramondo and R. Caminiti, Chem. Phys. Lett. 417, 200 (2006).
11. K.E. Riley, M. Pitoňák, J. Cǎerný and P. Hobza, J. Chem. Theory Comput. 6, 66 (2010).
12. K.E. Riley, M. Pitoňák, P. Jurečka and P. Hobza, Chem. Rev. 110, 5023 (2010).
13. L. Pejov, Chem. Phys. Lett. 339, 269 (2001).
14. P. Ottiger, C. Pfaffen, R. Leist, S. Leutwyler, R.A. Bachorz and W. Klopper, J. Phys. Chem. B 113, 2937 (2009).
15. S. Grimme, J Comput. Chem. 27, 1787 (2006).
16. M. Kabeláč, P. Hobza and V. Špirko, Phys. Chem. Chem. Phys. 11, 3885 (2009).
17. W.L. Jorgensen, D.S. Maxwell and J. Tirado-Rives, J. Am. Chem. Soc. 118, 11225 (1996).
18. W.L. Jorgensen and J. Tirado-Rives, Proc. Natl. Acad. Sci. USA 102, 6665 (2005).
19. N.A. McDonald and W.L. Jorgensen, J. Phys. Chem. B 102, 8049 (1998).
20. M. Piacenza and S. Grimme, Chem. Phys. Chem. 6, 1554 (2005).
21. R. Peverati and K.K. Baldridge, J. Chem. Theory Comput. 4, 2030 (2008).
22. Á. Vázquez-Mayagoitia, C.D. Sherrill, E. Aprà and B.G. Sumpter, J. Chem. Theory Comput. 6, 727 (2010).
23. L. Goerigkab and S. Grimme, Phys. Chem. Chem. Phys. 13, 6670 (2011).
24. S. Simon and M. Duran, J. Chem. Phys. 105, 11024 (1996).
25. S.F. Boys and F. Bernardi, Mol. Phys. 19, 553 (1970).
26. K.S. Thanthiriwatte, E.G. Hohenstein, L.A. Burns and C.D. Sherrill, J. Chem. Theory Comput. 7, 88 (2011).
27. L.A. Burns, Á. Vázquez-Mayagoitia, B.G. Sumpter and C.D. Sherrill, J. Chem. Phys. 134, 084107 (2011).
28. G.R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology (Oxford University Press, New York, 2001).
29. S.J. Grabowski, W.A. Sokalski and J. Leszczynski, J. Phys. Chem. A 109, 4331 (2005).
30. G. Gilli and P. Gilli, J. Mol. Struct. 552, 1 (2000).
31. T. Schwabe and S. Grimme, Phys. Chem. Chem. Phys. 9, 3397 (2007).
32. T. Takatani, E.G. Hohenstein, M. Malagoli, M.S. Marshall and C.D. Sherrill, J. Chem. Phys 132, 144104 (2010).
33. Y. Zhao and D.G. Truhlar, Acc. Chem. Res. 41, 157 (2008).
34. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Norm, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision C.01 (Gaussian, Inc., Wallingford CT, 2009).
35. R.F.W. Bader, Chem. Rev. 91, 893 (1991).
36. R.F.W. Bader, Atoms in Molecules: A Quantum Theory (Clarendon, Oxford, 1990).
37. T.A. Keith, AIMALL, Version 08.11.06, http://aim.tkgristmill.com
38. T. Lu, Multiwfn, version 2.1, http://multiwfn.codeplex.com
39. A.E. Reed, L.A. Curtiss and F. Weinhold, Chem. Rev. 88, 899 (1988).
40. J.P. Foster and F. Weinhold, J. Am. Chem. Soc. 102, 7211 (1980).
41. K. Morokuma, J. Chem. Phys. 55, 1236 (1971).
42. T. Ziegler and A. Rauk, Theor. Chim. Acta. 46, 1 (1978).
43. M. Lein and G. Frenking, in The First Forty Years, edited by C.F. Dykstra, G. Frenking, K.S. Kim, and G.E. Scuseria (Elsevier, Amsterdam, 2005).
44. E.J. Baerends, J. Autschbach, D. Bashford, A. Bérces, F.M. Bickelhaupt, C. Bo, P.M. Boerrigter, L. Cavallo, D.P. Chong, L. Deng, R.M. Dickson, D.E. Ellis, M. van Faassen, L. Fan, T.H. Fischer, C. Fonseca Guerra, A. Ghysels, A. Giammona, S.J.A. van Gisbergen, A.W. Gótz, J.A. Groeneveld, O.V. Gritsenko, M. Grüning, F.E. Harris, P. van den Hoek, C.R. Jacob, H. Jacobsen, L. Jensen, G. van Kessel, F. Kootstra, M.V. Krykunov, E. van Lenthe, D.A. McCormack, A. Michalak, M. Mitoraj, J. Neugebauer, V.P. Nicu, L. Noodleman, V.P. Osinga, S. Patchkovskii, P.H.T. Philipsen, D. Post, C.C. Pye, W. Ravenek, J.I. Rodri'uez, P. Ros, P.R.T. Schipper, G. Schreckenbach, M. Seth, J.G. Snijders, M. Solà, M. Swart, D. Swerhone, G. te Velde, P. Vernooijs, L. Versluis, L. Visscher, O. Visser, F. Wang, T.A. Wesolowski, E.M. van Wezenbeek, G. Wiesenekker, S.K. Wolff, T.K. Woo, A.L. Yakovlev and T. Ziegler, ADF 2012 (SCM, Amsterdam, The Netherlands, 2012).
45. M.P. Allen and D.J. Tildesley, Computer Simulation of Liquids (Clarendon, Oxford, 1987).
46. J.W. Ponder, Tinker, version 4.2, http://dasher.wustl.edu/tinker.
47. W.D. Cornell, P. Cieplak, C.I. Bayly, I.R. Gould, K.M. Merz Jr, D.M. Ferguson, D.C. Spellmeyer, T. Fox, J.W. Caldwell and P.A. Kollman, J. Am. Chem. Soc. 117, 5179 (1995).
48. R. Goddard, O. Heinemann and C. Kroger, Acta Crystall. Sect C 53, 1846 (1997).
49. I. Mata, I. Alkorta, E. Molins and E. Espinosa, Chem. Eur. J. 16, 2442 (2010).
50. M. Montejo, A. Navarro, G.J. Kearley, J. Vázquez and J.J. López-González, J. Am. Chem. Soc. 126, 15087 (2004).
51. S. Tsuzuki, K. Honda and R. Azumi, J. Am. Chem. Soc. 124, 12200 (2002).
52. P.L.A. Popelier, J. Phys. Chem. A 102, 1873 (1998).
53. P. Lipkowski, S.J. Grabowski, T.L. Robinson and J. Leszczynski, J. Phys. Chem. A 108, 10865 (2004).
54. J. Chocholousšová V. Špirko and P. Hobza, Phys. Chem. Chem. Phys. 6, 37 (2004).
55. X. Li, L. Liu and H.B. Schlegel, J. Am. Chem. Soc. 124, 9639 (2002).
56. I.V. Alabugin, M. Manoharan, S. Peabody and F. Weinhold, J. Am. Chem. Soc. 125, 5973 (2003).
57. P.-P. Zhou and W.-Y. Qiu, ChemPhysChem 10, 1847 (2009).
58. P.-P. Zhou and W.-Y. Qiu, J. Phys. Chem. A 113, 10306 (2009).
59. P. Su and H. Li, J. Chem. Phys. 131, 014102 (2009).
60. S. Grimme, J. Antony, T. Schwabe and C. Mück-Lichtenfeld, Org. Biomol. Chem. 5, 741 (2007).
61. CRC Handbook of Chemistry and Physics, 90th edn (Internet Version 2010), edited by D.R. Lide, (CRC Press/Taylor and Francis, Boca Raton, 2010).
62. U. Domańaska and M. Zawadzk, J. Chem. Eng. Data. 55, 5413 (2010).
63. D.W. Scott, W.T. Berg, I.A. Hossenlopp, W.N. Hubbard, J.F. Messerly, S.S. Todd, D.R. Douslin, J.P. McCullough and G. Waddington, J. Phys. Chem. 71, 2263 (1967).
64. M.D. Elola and B.M. Ladanyi, J. Chem. Phys. 122, 224508 (2005).
65. R. Vácha, L. Cwiklik, J. Řezáč, P. Hobza, P. Jungwirth, K. Valsaraj, S. Bahr and V. Kempter, J. Phys. Chem. A 112, 4942 (2008).
66. T.F. Headen, C.A. Howard, N.T. Skipper, M.A. Wilkinson, D.T. Bowron and A.K. Soper, J. Am. Chem. Soc. 132, 5735 (2010).
67. G. Desiraju, Acc. Chem. Res. 35, 565 (2002).
68. A. Luzar and D. Chandler, J. Chem. Phys. 98, 8160 (1993).
69. Y. Lei, H. Li, R. Zhang and S. Han, J. Phys. Chem. B 111, 14370 (2007).