Factors controlling asymmetrization of the simplest linear I 3 - and I 4 2- polyiodides with implications for the nature of halogen bonding

Crystal Growth and Design

Volumn 12, Issue 4, 2012, Pages 1762-1771

  Manca, Gabriele ^a   Ienco, Andrea ^a   Mealli, Carlo ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; CENTRAL ATOM; COUNTERIONS; CRYSTAL DATA; DELOCALIZATIONS; DENSITY FUNCTIONAL THEORY CALCULATIONS; ELECTRON TRANSFER; ELECTROSTATIC ATTRACTIONS; ENERGY INFORMATION; HALOGEN BONDING; INTRINSIC ENERGY; MOLECULAR ELECTROSTATIC POTENTIALS; NUCLEOPHILIC ATTACK; ORBITAL ENERGY; ORBITAL OVERLAP; POINT CHARGE; POLYIODIDES; POSITIVE CHARGES; SIMPLEST LINEAR; STATE EFFECTS;

CHEMICAL BONDS; COMPLEXATION; ELECTRONEGATIVITY; ELECTROSTATICS;

IODINE;

EID: 84859378525     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg201154n     Document Type: Article

References (117)

1. Balzani, V., Credi, A., and Venturi, M. Molecular Devices and Machines; Wiley-VCH: Weinheim, Germany, 2003.
2. Browne, W. R.; Feringa, B. L. Nat. Nanotechnol. 2006, 1, 25
3. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72
4. Credi, A. Aust. J. Chem. 2006, 59, 157
5. Tian, H.; Wang, Q. C. Chem. Soc. Rev. 2006, 35, 361
6. Saha, S.; Stoddart, J. F. Chem. Soc. Rev. 2007, 36, 77
7. Silvi, S.; Venturi, M.; Credi, A. J. Mater. Chem. 2009, 19, 2279
8. Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172
9. Luo, Y.; Collier, C. P.; Jeppesen, J. O.; Nielsen, K. A.; DeIonno, E.; Ho, G.; Perkins, J.; Tseng, H.-R.; Yamamoto, T.; Stoddart, J. F.; Heath, J. R. ChemPhysChem 2002, 3, 519
10. Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. F. Science 2004, 306, 2055
11. Green, J. E.; Choi, J. W.; Boukai, A.; Bunimovich, Y.; Johnston-Halperin, E.; DeIonno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shin, Y. S.; Tseng, H.-R.; Stoddart, J. F.; Heath, J. R. Nature 2007, 445, 414
12. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174
13. Barthelet, K.; Marrot, J.; Riou, D.; Ferey, G. Angew. Chem., Int. Ed. 2002, 41, 281
14. Gao, E. Q.; Bai, S. Q.; Wang, Z. M.; Yan, C. H. J. Am. Chem. Soc. 2003, 125, 4984
15. Minguet, M.; Luneau, D.; Lhotel, E.; Villar, V.; Paulsen, C.; Amabilino, D. B.; Veciana, J. Angew. Chem., Int. Ed. 2002, 41, 586
16. Patrick, B. O.; Reiff, W. M.; Sanchez, V.; Storr, A.; Thompson, R. C. Inorg. Chem. 2004, 43, 2330
17. Galan-Mascaros, J. R.; Dunbar, K. R. Angew. Chem., Int. Ed. 2003, 42, 2289
18. Lehn, J.-M. Pure Appl. Chem. 1978, 50, 871
19. Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1988, 27, 89
20. Lehn, J.-M. Supramolecular Chemistry. Concepts and Perspectives; VCH: Weinheim, 1995.
21. Metrangolo, P.; Resnati, G. Science 2008, 321, 918
22. Hassel, O. Science 1970, 170, 497
23. Bent, H. A. Chem. Rev. 1968, 68, 587
24. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386
25. Weiss, R.; Schwab, O.; Hampel, F. Chem.-Eur. J. 1999, 5, 968
26. Metrangolo, P.; Resnati, G. Chem.-Eur. J. 2001, 7, 2511
27. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad. Sci. U: S. A. 2004, 101, 16789
28. Howard, E. I.; Sanishvili, R; Cachau, R. E.; Mitschler, A.; Chevrier, B.; Barth, P.; Lamour, V.; Van Zandt, M. Proteins: Struct., Funct., Bioinf. 2004, 55, 792
29. Rissanen, S. K. CrystEngComm 2008, 10, 1107
30. Ritter, S. K. Chem. Eng. News 2009, 11, 1187
31. Alkorta, I.; Rozas, I.; Elguero, J. J. Phys. Chem. A 1998, 102, 9728
32. Slifkin, M. A. Spectrochim. Acta 1971, 27A, 1999
33. Was, B. K.; Majee, B. Indian Chem. Soc. 1968, 45, 1064
34. Fieser, L. F. J. Am. Chem. Soc. 1926, 45, 2922
35. Shirakawa, H.; Itoh, T.; Ikeda, S. Makromol. Chem. 1978, 179, 1565
36. Day, D. R.; Lando, J. B. J. Appl. Polym. Sci. 1981, 26, 1605
37. Grotthus, C. J. T. Ann. Chim. 1806, 58, 54
38. Papageorgiou, N.; Athanassov, Y.; Armand, M.; Bonhote, P.; Patterson, H.; Azam, A.; Grätzel, M. J. Electrochem. Soc. 1996, 143, 3099
39. Stegemann, H.; Reiche, A.; Schnittke, A.; Fullbier, H. Electrochim. Acta 1992, 183, 379
40. Grätzel, M. Nature 2001, 414, 383
41. Grätzel, M. J. Photochem. Photobiol. C 2003, 4, 145
42. Grätzel, M. Chem. Lett. 2005, 34, 8
43. Kawano, R.; Watanabe, M. Chem. Commun. 2005, 2107
44. Svensson, P. H.; Kloo, L. Chem. Rev. 2003, 103, 1649 and references therein.
45. Desiraju, G. R. The crystal As a Supramolecular Entity; John Wiley & Sons: New York, 1996.
46. Wieczorrek, C. Acta Crystallogr., Sect. C 2000, 56, 1082
47. van Bolhuis, F.; Koster, P. B.; Migchelsen, T. Acta Crystallogr. 1967, 23, 90
48. Rosssi, M.; Marzilli, L. G.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1978, 34, 2030
49. Cambridge Structural Database System, Cambridge Crystallographic Data Centre, Cambridge, UK Version 5.32.
50. Herbstein, F. H.; Kapon, M.; Schwotzer, W. Helv. Chim. Acta 1983, 35
51. Herbstein, F. H.; Schwotzer, W. J. Am. Chem. Soc. 1984, 106, 2367
52. Illioudis, C. A.; Steed, J. W. CrystEngComm 2004, 6, 239
53. Long, De-L.; Hu, H.-M.; Chen, J.-T.; Huang, J.-S. Acta Crystallogr., Sect C 1999, 55, 339
54. Rabenau, A.; Schulz, H.; Stoeger, W. Naturwissen. 1976, 63, 245
55. Muller, M.; Albrecht, M.; Gossen, V.; Peters, T.; Hoffmann, A.; Raabe, G.; Valkonen, A.; Rissanen., K. Chem.-Eur. J. 2010, 16, 12446
56. Abate, A.; Brischetto, M.; Cavallo, G.; Lahtinen, M.; Metrangolo, P.; Pilati, T.; Radice, S.; Resnati, G.; Rissanen, K.; Terraneo, G. Chem. Commun. 2010, 46, 2724
57. Hitchcock, P. B.; Hughes, D. L.; Leigh, G. J.; Sanders, J. R.; de Souza, J.; McGarry, C. J.; Larkworthy, L. F. J. Chem. Soc., Dalton Trans. 1984, 3683
58. Redel, E.; Rohr, C.; Janiak, C. Chem. Commun. 2009, 2103
59. Dubler, E.; Linowsky, L. Helv. Chim. Acta 1975, 58, 283
60. McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Chem. Commun. 2007, 3814
61. Spackman, M. A.; Byrom, P. G. Chem. Phys. Lett. 1997, 267, 215
62. McKinnon, J. J.; Mitchell, A. S.; Spackman, M. A. Chem.-Eur. J. 1998, 4, 2136
63. Hassel, O. Mol. Phys. 1958, 1, 241
64. Stewart, R. F. J. Chem. Phys. 1972, 57-1664
65. A and ρ(r) is the molecular electronic density. V (r) = - Z A | R A - r | - ∫ ρ (r ′) d r ′ | r ′ - r |
66. Brinck, T.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem., Quantum. Biol. Symp. 1992, 19, 57
67. Murray, J. S.; Paulsen, K.; Politzer P. Proc. Indian Acad. Sci. (Chem. Sci.) 1994, 106, 267
68. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. J. Mol. Model. 2007, 13, 305
69. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. J. Mol. Model. 2007, 13, 291
70. Pimentel, C. G. J. Chem. Phys. 1951, 19, 446
71. Hach, R. J.; Rundle, R. E. J. Am. Chem. Soc. 1951, 73, 4321
72. Mealli, C.; Proserpio, D. M. J. Chem. Educ. 1990, 67, 399
73. Mealli, C.; Ienco, A.; Proserpio, D. M. Book of Abstracts of the XXXIII ICCC, Florence, Ed. CNR, Area della Ricerca di Firenze; 1998; p 510.
74. Munzarova, M. L.; Hoffmann, R. J. Am. Chem. Soc. 2002, 124, 4787
75. Landrum, G. A.; Goldberg, N.; Hoffmann, R. J. Chem. Soc., Dalton Trans. 1997, 3605
76. Bigoli, F.; Deplano, P.; Ienco, A.; Mealli, C.; Mercuri, M. L.; Pellinghelli, M. A.; Pintus, G.; Saba, G.; Trogu, E. F. Inorg. Chem. 1999, 38, 4626
77. Watson, W. H.; Kashyap, R. P. Acta Crystallogr., Sect. C 1990, 46, 2312
78. Ambrosetti, R.; Bellucci, G.; Bianchini, R.; Bigoli, F.; Deplano, P.; Pellinghelli, M. A.; Trogu, E. F. J. Chem. Soc., Perkin Trans. 2 1991, 339
79. Hirva, P.; Haukka, M.; Jakonen, M.; Moreno, M. A. J. Mol. Mod. 2008, 17, 171
80. Lombardi, J. R.; Davis, B. Chem. Rev. 2002, 102, 2431
81. Barden, C. J.; Rienstra-Kiracofe, J. C.; Schaefer, H. F., III J. Chem. Phys. 2000, 113, 690
82. Yanagisawa, S.; Tsuneda, T.; Hirao, K. J. Chem. Phys. 2000, 112, 545
83. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 0.9, Revision B.01 ed.; Gaussian, Inc.: Wallingford CT, 2010.
84. Cízek, J. J. Chem. Phys. 1966, 45, 4256
85. Cízek, J. Adv. Chem. Phys. 1969, 14, 35
86. Cízek, J.; Paldus, J. Int. J. Quantum Chem. 1971, 5, 359
87. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618
88. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
89. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Phys. 2005, 123, 194101: 1
90. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theor. Comput. 2006, 2, 364
91. Grimme, S. J. Chem. Phys. 2006, 124, 34108
92. Datta, S. N.; Ewig, C. S.; Wazer, J. R. V. J. Mol. Struct. 1978, 48, 407
93. Svensson, P. H.; Kloo, L. J. Chem. Soc., Dalton Trans. 2000, 2449
94. Barone, V.; Cossi, M. J. Phys. Chem. 1998, A102, 1995
95. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669
96. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2001.
97. Parvez, M.; Wang, M.; Boorman, P. M. Acta Crystallogr., Sect. C 1996, 52, 377
98. Tasman, H. A.; Boswijk, K. H. Acta Crystallogr. 1957, 10, 596
99. Mooney-Slater, R. C. L. Acta Crystallogr. 1959, 12, 187
100. Hirshfeld, F. L. Theor. Chim. Acta 1977, 44, 129
101. Migchelsen, T.; Vos, A. Acta Crystallogr. 1967, 23, 796
102. Naito, T.; Tateno, A.; Udagawa, T.; Kobayashi, H.; Kato, R.; Kobayashi, A.; Nogami, T. J. Chem. Soc., Faraday Trans. 1994, 90, 763)
103. Tateno, A.; Udagawa, T.; Naito, T.; Kobayashi, H.; Kobayashi, A.; Nogami, T. J. Mater. Chem. 1994, 4, 1559)
104. Muetterties, E. L.; Mahler, W.; Schmutzler, R. Inorg. Chem. 1963, 2, 613
105. Coe, B. J.; Glenwright, S. J. Coord. Chem. Rev. 2000, 203, 5
106. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 4 th ed.; Wiley-Interscience: New York, 2005.
107. Hartley, F. R. Chem. Soc. Rev. 1973, 2, 163
108. Weiss, R.; Schwab, O.; Hampel, F. Chem.-Eur. J. 1999, 5, 968
109. Wang, Y.-Q.; Wang, Z.-M.; Liao, C.-S.; Yan, C.-H. Acta Crystallogr., Sect. C 1999, 55, 1503
110. Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Clarendon Press: Oxford, 1990.
111. Nelyubina, Y. V.; Antipin, M. Yu.; Dunin, D. S.; Kotov, V. Yu.; Lyssenko, K. A. Chem. Commun. 2010, 46, 5325
112. Gorelsky, S. I. AOMix: Program for Molecular Orbital Analysis, version 6.5, 2011,; University of Ottawa, http://www.sg-chem.net/.
113. Gorelsky, S. I.; Lever, A. B. P. J. Organomet. Chem. 2001, 635, 187
114. Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. J. Chem. Phys. 1987, 86, 866
115. Andrae, D.; Haussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123
116. Fukui, K. Acc. Chem. Res. 1981, 14, 363
117. MOLEKEL 4.0; Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. Swiss Center for Scientific Computing: Manno, Switzerland, 2000.