Energetic and geometrical evidence of nonbonding character of some intramolecular halogen⋯oxygen and other Y⋯Y interactions

Journal of Physical Chemistry A

Volumn 116, Issue 14, 2012, Pages 3753-3764

  Jabłoński, Miroslaw ^a  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CRITICAL POINTS; BOND PATHS; CONTACT FORMATION; ELECTROSTATIC POTENTIALS; ESTIMATING METHOD; GEOMETRICAL CHANGES; HIGH-LEVEL AB INITIO CALCULATIONS; INTERACTION ENERGIES; INTRAMOLECULAR INTERACTIONS; ISO SURFACE; LATERAL CONTACT; NEGATIVE VALUES; POSITIVE VALUE; QUANTUM THEORY OF ATOMS IN MOLECULES; STABILIZING INTERACTIONS;

CHLORINE; MOLECULES; QUANTUM THEORY;

BROMINE;

EID: 84859790085     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp300993b     Document Type: Article

References (119)

1. Brinck, T.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem., Quantum Biol. Symp. 1992, 19, 57-64
2. Murray, J. S.; Paulsen, K.; Politzer, P. Proc. Indian Acad. Sci., Chem. Sci. 1994, 106, 267-275
3. Eskandari, K.; Zariny, H. Chem. Phys. Lett. 2010, 492, 9-13
4. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. J. Mol. Model. 2007, 13, 305-311
5. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. J. Mol. Model. 2007, 13, 291-296
6. Politzer, P.; Murray, J. S.; Clark, T. Phys. Chem. Chem. Phys. 2010, 12, 7748-7757
7. Lommerse, J. P. M; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108-3116
8. Zou, J.-W.; Jiang, Y.-J.; Guo, M.; Hu, G.-X.; Zhang, B.; Liu, H.-C.; Yu, Q.-S. Chem. - Eur. J. 2005, 11, 740-751
9. Riley, K. E.; Hobza, P. J. Chem. Theory Comput. 2008, 4, 232-242
10. Bent, H. A. Chem. Rev. 1968, 68, 587-648
11. Hassel, O. Nobel Lectures, Chemistry 1963-1970; Elsevier: Amsterdam, 1972.
12. Ramasubbu, N.; Parthasarathy, R.; Murray-Rust, P. J. Am. Chem. Soc. 1986, 108, 4308-4314
13. Legon, A. C. Angew. Chem., Int. Ed. 1999, 38, 2686-2714
14. Valerio, G.; Raos, G.; Meille, S. V.; Metrangolo, P.; Resnati, G. J. Phys. Chem. A 2000, 104, 1617-1620
15. Romaniello, P.; Lelj, F. J. Phys. Chem. A 2002, 106, 9114-9119
16. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789-16794
17. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386-395
18. Palusiak, M.; Grabowski, S. J. Struct. Chem. 2007, 18, 859-865
19. Metrangolo, P.; Resnati, G. Halogen Bonding: Fundamentals and Applications, Structure and Bonding No. 126; Springer: Berlin, 2008.
20. Murray, J. S.; Concha, M. C.; Lane, P.; Hobza, P.; Politzer, P. J. Mol. Model. 2008, 14, 699-704
21. Alkorta, I.; Blanco, F.; Solimannejad, M.; Elguero, J. J. Phys. Chem. A 2008, 112, 10856-10863
22. Politzer, P.; Murray, J. S. In Practical Aspects of Computational Chemistry; Leszczynski, J.; Shukla, M., Eds.; Springer: Heidelberg, 2009.
23. Murray, J. S.; Lane, P.; Politzer, P. J. Mod. Model. 2009, 15, 723-729
24. Lu, Y.; Shi, T.; Wang, Y.; Yang, H.; Yan, X.; Luo, X.; Jiang, H.; Zhu, W. J. Med. Chem. 2009, 52, 2854-2862
25. Li, Q.; Wang, Y.; Liu, Z.; Li, W.; Cheng, J.; Gong, B.; Sun, J. Chem. Phys. Lett. 2009, 469, 48-51
26. Cheng, J.; Li, R.; Li, Q.; Jing, B.; Liu, Z.; Li, W.; Gong, B.; Sun, J. J. Phys. Chem. A 2010, 114, 10320-10325
27. Li, Q.; Xu, X.; Liu, T.; Jing, B.; Li, W.; Cheng, J.; Gong, B.; J., S. Phys. Chem. Chem. Phys. 2010, 12, 6837-6843
28. Palusiak, M. J. Mol. Struct.: THEOCHEM 2010, 945, 89-92
29. Roper, L. C.; Prasang, C.; Whitwood, A. C.; Bruce, D. W. CrystEngComm. 2010, 12, 3382-3384
30. Grabowski, S. J. J. Phys. Chem. A 2011, 115, 12340-12347
31. Jabłoński, M.; Palusiak, M. J. Phys. Chem. A 2012, 116, 2322-2332
32. Politzer, P.; Murray, J. S.; Concha, M. C. J. Mol. Model. 2008, 14, 659-665
33. Vila, A.; Mosquera, R. A. J. Mol. Struct.: THEOCHEM 2001, 546, 63-72
34. Matta, C. F.; Castillo, N.; Boyd, R. J. J. Phys. Chem. A 2005, 109, 3669-3681
35. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: New York, 1990.
36. Popelier, P. L. A. Atoms in Molecules. An Introduction; Longman: Singapore, 2000.
37. Bader, R. F. W. J. Phys. Chem. A 1998, 102, 7314-7323
38. Allen, F. H. Acta Crystallogr. 2002, B58, 380
39. Matta, C. F.; Hernández-Trujillo, J.; Tang, T.-H.; Bader, R. F. W. Chem. - Eur. J. 2003, 9, 1940-1951
40. Bader, R. F. W.; Fang, D.-C. J. Chem. Theory Comput. 2005, 1, 403-414
41. Bader, R. F. W. Chem. - Eur. J. 2006, 12, 2896-2901
42. Bader, R. F. W. J. Phys. Chem. A 2010, 114, 7431-7444
43. Cioslowski, J.; Mixon, S. T.; Edwards, W. D. J. Am. Chem. Soc. 1991, 113, 1083-1085
44. Cioslowski, J.; Mixon, S. T. J. Am. Chem. Soc. 1992, 114, 4382-4387
45. Cioslowski, J.; Mixon, S. T. Can. J. Chem. 1992, 70, 443-449
46. Cioslowski, J.; Edgington, L.; Stefanov, B. B. J. Am. Chem. Soc. 1995, 117, 10381-10384
47. Haaland, A.; Shorokhov, D. J.; Tverdova, N. V. Chem. - Eur. J. 2004, 10, 4416-4421
48. Poater, J.; Solà, M.; Bickelhaupt, F. M. Chem. - Eur. J. 2006, 12, 2889-2895
49. Poater, J.; Solà, M.; Bickelhaupt, F. M. Chem. - Eur. J. 2006, 12, 2902-2905
50. Strenalyuk, T.; Haaland, A. Chem. - Eur. J. 2008, 14, 10223-10226
51. Cerpa, E.; Krapp, A.; Vela, A.; Merino, G. Chem. - Eur. J. 2008, 14, 10232-10234
52. Cerpa, E.; Krapp, A.; Flores-Moreno, R.; Donald, K. J.; Merino, G. Chem. - Eur. J. 2009, 15, 1985-1990
53. Grimme, S.; Mück-Lichtenfeld, C.; Erker, G.; Kehr, G.; Wang, H.; Beckers, H.; Willner, H. Angew. Chem., Int. Ed. 2009, 48, 2592-2595
54. Bickelhaupt, F. M.; Baerends, E. J. In Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; Wiley: New York, 2000; Vol. 15.
55. te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Guerra, C. F.; Van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931
56. Kitaura, K.; Morokuma, K. Int. J. Quantum Chem. 1976, 10, 325
57. Wiberg, K. B. Tetrahedron 1968, 24, 1083
58. Krapp, A.; Frenking, G. Chem. - Eur. J. 2007, 13, 8256-8270
59. McNaught, A. D.; Wilkinson, A. IUPAC Compedium of Chemical Terminology, 2 nd ed.; IUPAC: Research Triangle Park, NC, 1997.
60. Bader, R. F. W. J. Phys. Chem. A 2009, 113, 10391-10396
61. Craw, J. S.; Bacskay, G. B. J. Chem. Soc., Faraday Trans. 1992, 88, 2315
62. Buemi, G.; Zuccarello, F. J. Mol. Struct. (Theochem) 2002, 581, 71
63. Jabłoński, M.; Kaczmarek, A.; Sadlej, A. J. J. Phys. Chem. A 2006, 110, 10890-10898
64. Jabłoński, M. Chem. Phys. 2010, 376, 76-83
65. Buemi, G. Hydrogen Bonding-New Insights, Vol. 3, Grabowski, S. J. (Eds.); Springer: Dordrecht, The Netherlands, 2006.
66. Schuster, P. Mh. Chem 1969, 100, 2084
67. Schuster, P. The Hydrogen Bond, Vol. I, Schuster, P.; Zundel, G.; Sandorfy, C. (Eds.); North-Holland: Amsterdam, The Netherlands, 1976.
68. Murthy, A. S. N.; Rao, C. N. R. J. Mol. Struct. 1970, 6, 253
69. Falk, H.; Hofer, O.; Lehner, H. Mh. Chem. 1974, 105, 995
70. Estácio, S. G.; do Couto, P. C.; Costa Cabral, B. J.; Minas da Piedade, M. E.; Martinho Simoes, J. A. J. Phys. Chem. A 2004, 108, 10834
71. Roy, D.; Sunoj, R. B. J. Phys. Chem. A 2006, 110, 5942
72. Buemi, G.; Zuccarello, F.; Venuvanalingam, P.; Ramalingam, M.; Ammal, S. S. C. J. Chem. Soc., Faraday Trans. 1998, 94, 3313
73. Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796
74. George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Theor. Chim. Acta 1975, 38, 121
75. Hehre, W. J.; Radom, L.; von Schleyer, P.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
76. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170
77. Deshmukh, M. M.; Gadre, S. R.; Bartolotti, L. J. J. Phys. Chem. A 2006, 110, 12519
78. Deshmukh, M. M.; Suresh, C. H.; Gadre, S. R. J. Phys. Chem. A 2007, 111, 6472
79. Deshmukh, M. M.; Bartolotti, L. J.; Gadre, S. R. J. Phys. Chem. A 2008, 112, 312
80. Deshmukh, M. M.; Gadre, S. R. J. Phys. Chem. A 2009, 113, 7927
81. Scheiner, S.; Kar, T.; Čuuma, M. J. Phys. Chem. A 1997, 101, 5901
82. Cuma, M.; Scheiner, S.; Kar, T. J. Mol. Struct. (Theochem) 1999, 467, 37
83. Chung, G.; Kwon, O.; Kwon, Y. J. Phys. Chem. A 1997, 101, 9415
84. Pakiari, A. H.; Eskandari, K. J. Mol. Struct.: THEOCHEM 2007, 806, 1-7
85. Frisch, M. J. "Gaussian 03", Gaussian, Inc.:, Wallingford, CT, 2004.
86. Möller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618
87. Almloff, J.; Korsell, K.; Faegri, K., Jr. J. Comput. Chem. 1982, 3, 385
88. Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503
89. Head-Gordon, M.; Pople, J. A. J. Chem. Phys. 1988, 89, 5777
90. Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 275
91. Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 281
92. Head-Gordon, M.; Head-Gordon, T. Chem. Phys. Lett. 1994, 220, 122
93. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796
94. Davidson, E. R. Chem. Phys. Lett. 1996, 260, 514
95. Peterson, K. A.; Shepler, B. C.; Figgen, D.; Stoll, H. J. Phys. Chem. A 2006, 110, 13877
96. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
97. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
98. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
99. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639
100. Curtiss, L. A.; McGrath, M. P.; Blandeau, J.-P.; Davis, N. E.; Binning, R. C.; Radom, J. L. J. Chem. Phys. 1995, 103, 6104
101. Glukhovstev, M. N.; Pross, A.; McGrath, M. P.; Radom, L. J. Chem. Phys. 1995, 103, 1878
102. Jabłoński, M.; Sadlej, A. J. J. Phys. Chem. A 2007, 111, 3423-3431
103. Ortiz, C. O.; Bo, C. "Xaim", Universitat Rovira i Virgili: Tarragona. Spain, accessed November 2009, http://www.quimica.urv.es/XAIM/.
104. Biegler-König, F. W. "AIM2000 program", University of Applied Sciences, Bielefeld, Germany, 2000.
105. Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. "Molekel 4.3", Swiss Center for Scientific Computing: Manno, Switzerland, 2000-2002.
106. Portmann, S.; Lüthi, H. P. Chimia 2000, 54, 766-770
107. Jabłoński, M.; Sadlej, A. J. Chem. Phys. Lett. 2008, 463, 322-326
108. Cioslowski, J.; O'Connor, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086-1089
109. Cioslowski, J.; Mixon, S. T.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 4751-4755
110. Mandado, M.; Graña, A. M.; Mosquera, R. A. Phys. Chem. Chem. Phys. 2004, 6, 4391-4396
111. Rozas, I.; Alkorta, I.; Elguero, J. J. Phys. Chem. A 2001, 105, 10462
112. Varnali, T.; Hargittai, I. J. Mol. Struct. (Theochem) 1996, 388, 315
113. Jabłoński, M. Chem. Phys. Lett. 2009, 477, 374
114. Bader, R. F. W.; Caroll, M. T.; Cheeseman, J. R.; Chang, C. J. Am. Chem. Soc. 1987, 109, 7968-7979
115. Jabłoński, M. J. Mol. Struct.: THEOCHEM 2007, 820, 118-127
116. Li, X.; Liu, L.; Schlegel, H. B. J. Am. Chem. Soc. 2002, 124, 9639
117. Papadopoulos, M.; Sadlej, A. J. Chem. Phys. Lett. 1998, 288, 377
118. Jabłoński, M.; Solà, M. J. Phys. Chem. A 2010, 114, 10253-10260
119. Cruz, S. A.; Soullard, J. Chem. Phys. Lett. 2004, 391, 138