Multinuclear solid-state magnetic resonance as a sensitive probe of structural changes upon the occurrence of halogen bonding in co-crystals

Chemistry - A European Journal

Volumn 19, Issue 36, 2013, Pages 11949-11962

  Widdifield, Cory M ^a,c   Cavallo, Gabriella ^b   Facey, Glenn A ^a   Pilati, Tullio ^b   Lin, Jingxiang ^b   Metrangolo, Pierangelo ^b   Resnati, Giuseppe ^b   Bryce, David L ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b NFMLab DCMIC G Natta   (Italy)

^c UNIVERSITÉ DE LYON   (France)

Author keywords

co crystallization; halogen bonds; NMR spectroscopy; noncovalent interactions; X ray diffraction

Indexed keywords

COCRYSTALLIZATION; HALOGEN BONDS; NON-COVALENT INTERACTION; QUADRUPOLAR COUPLING CONSTANTS; QUANTUM CHEMICAL CALCULATIONS; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID-STATE NMR SPECTROSCOPY; ZEROTH-ORDER REGULAR APPROXIMATIONS;

ELECTRIC FIELDS; EXPERIMENTS; FLUORINE; HALOGEN COMPOUNDS; HYDROGEN BONDS; IONS; MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBES; QUANTUM CHEMISTRY; X RAY DIFFRACTION;

IODINE;

EID: 84883244653     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300809     Document Type: Article

References (112)

1. H. A. Bent, Chem. Rev. 1968, 68, 587-648.
2. D. Hadži, H. W. Thompson, Hydrogen Bonding: Papers Presented at the Symposium on Hydrogen Bonding Held at Ljubljana, July 29-August 3, 1957, Pergamon, London, 1959.
3. G. C. Pimentel, A. L. McClellan, The Hydrogen Bond, W. H. Freeman and Company, San Francisco, 1960.
4. T. Steiner, Angew. Chem. 2002, 114, 50-80
5. Angew. Chem. Int. Ed. 2002, 41, 48-76.
6. W. C. Hamilton, J. A. Ibers, Hydrogen Bonding in Solids, W. A. Benjamin, New York, 1968.
7. F. Cangelosi, M. T. Shaw, Polym. Plast. Technol. Eng. 1983, 21, 13-98.
8. G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond: In Structural Chemistry and Biology, Oxford University Press, New York, 1999.
9. P. Gamez, T. J. Mooibroek, S. J. Teat, J. Reedijk, Acc. Chem. Res. 2007, 40, 435-444.
10. B. L. Schottel, H. T. Chifotides, K. R. Dunbar, Chem. Soc. Rev. 2008, 37, 68-83.
11. I. D. Giles, H. T. Chifotides, M. Shatruk, K. R. Dunbar, Chem. Commun. 2011, 47, 12604-12606.
12. J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324.
13. M. Cametti, A. D. Cort, L. Mandolini, Chem. Sci. 2012, 3, 2119-2122.
14. M. Taddei, F. Costantino, R. Vivani, C. Sangregorio, L. Sorace, L. Castelli, Cryst. Growth Des. 2012, 12, 2327-2335.
15. M. Egli, S. Sarkhel, Acc. Chem. Res. 2007, 40, 197-205.
16. Y. V. Nelyubina, P. Y. Barzilovich, M. Y. Antipin, S. M. Aldoshin, K. A. Lyssenko, ChemPhysChem 2011, 12, 2895-2898.
17. M. Nishio, M. Hirota, Y. Umezawa, The CH-π Interaction: Evidence, Nature and Consequences, Wiley, Weinheim, 1998.
18. C. J. Pace, D. Kim, J. Gao, Chem. Eur. J. 2012, 18, 5832-5836.
19. M. J. Plevin, D. L. Bryce, J. Boisbouvier, Nat. Chem. 2010, 2, 466-471.
20. M. Bardajía, A. Laguna, Eur. J. Inorg. Chem. 2003, 3069-3079.
21. P. Pyykkö, Angew. Chem. 2004, 116, 4512-4557
22. Angew. Chem. Int. Ed. 2004, 43, 4412-4456.
23. I. O. Koshevoy, L. Koskinen, E. S. Smirnova, M. Haukka, T. A. Pakkanen, A. S. Melnikov, S. P. Tunik, Z. Anorg. Allg. Chem. 2010, 636, 795-802.
24. C. Estarellas, A. Frontera, D. Quiñonero, P. M. Deyà, ChemPhysChem 2011, 12, 2742-2750.
25. A. Ebrahimi, M. Habibi, R. S. Neyband, A. R. Gholipour, Phys. Chem. Chem. Phys. 2009, 11, 11424-11431.
26. Y. Guo, Y. Ma, N. Zhou, Z.-Q. Liu, Q.-L. Wang, S.-P. Yan, D.-Z. Liao, Z. Anorg. Allg. Chem. 2010, 636, 865-871.
27. N. Ma, Y. Zhang, B. Ji, A. Tian, W. Wang, ChemPhysChem 2012, 13, 1411-1414.
28. Q. Li, X. Xu, T. Liu, B. Jing, W. Li, J. Cheng, B. Gong, J. Sun, Phys. Chem. Chem. Phys. 2010, 12, 6837-6843.
29. A. R. Voth, P. Khuu, K. Oishi, P. S. Ho, Nat. Chem. 2009, 1, 74-79.
30. P. Metrangolo, G. Resnati, Chem. Eur. J. 2001, 7, 2511-2519.
31. P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo, Angew. Chem. 2008, 120, 6206-6220
32. Angew. Chem. Int. Ed. 2008, 47, 6114-6127.
33. G. Cavallo, P. Metrangolo, T. Pilati, G. Resnati, M. Sansotera, G. Terraneo, Chem. Soc. Rev. 2010, 39, 3772-3783.
34. G. Cavallo, S. Biella, J. Lü, P. Metrangolo, T. Pilati, G. Resnati, G. Terraneo, J. Fluorine Chem. 2010, 131, 1165-1172.
35. F. Guthrie, J. Chem. Soc. 1863, 16, 239-244.
36. I. Remsen, J. F. Norris, Am. Chem. J. 1896, 18, 90-96.
37. P. Politzer, P. Lane, M. C. Concha, Y. Ma, J. S. Murray, J. Mol. Model. 2007, 13, 305-311.
38. A. Priimagi, M. Saccone, G. Cavallo, A. Shishido, T. Pilati, P. Metrangolo, G. Resnati, Adv. Mater. 2012, 24, OP 345 -OP 352.
39. E. Cariati, G. Cavallo, A. Forni, G. Leem, P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, S. Righetto, G. Terraneo, E. Tordin, Cryst. Growth Des. 2011, 11, 5642-5648.
40. E. Parisini, P. Metrangolo, T. Pilati, G. Resnati, G. Terraneo, Chem. Soc. Rev. 2011, 40, 2267-2278.
41. R. Berger, G. Resnati, P. Metrangolo, E. Weber, J. Hulliger, Chem. Soc. Rev. 2011, 40, 3496-3508.
42. M. Erdélyi, Chem. Soc. Rev. 2012, 41, 3547-3557.
43. P. Politzer, J. S. Murray, T. Clark, Phys. Chem. Chem. Phys. 2010, 12, 7748-7757.
44. P. Metrangolo, Y. Carcenac, M. Lahtinen, T. Pilati, K. Rissanen, A. Vij, G. Resnati, Science 2009, 323, 1461-1464.
45. D. L. Bryce, G. D. Sward, Magn. Reson. Chem. 2006, 44, 409-450.
46. C. M. Widdifield, R. P. Chapman, D. L. Bryce, Annu. Rep. Nucl. Magn. Reson. Spectrosc. 2009, 66, 195-326.
47. R. P. Chapman, C. M. Widdifield, D. L. Bryce, Prog. Nucl. Magn. Reson. Spectrosc. 2009, 55, 215-237.
48. B. J. Butler, J. M. Hook, J. B. Harper, Annu. Rep. Nucl. Magn. Reson. Spectrosc. 2011, 73, 63-82.
49. D. L. Bryce, C. M. Widdifield, R. P. Chapman, R. J. Attrell, NMR of Quadrupolar Nuclei in Solid Materials (Eds.:, R. E. Wasylishen, S. E. Ashbrook, S. Wimperis,), Wiley, Chichester (UK), 2012, Chapter 19, pp. 321-348.
50. F. A. Perras, D. L. Bryce, Angew. Chem. 2012, 124, 4303-4306
51. Angew. Chem. Int. Ed. 2012, 51, 4227-4230.
52. R. J. Attrell, C. M. Widdifield, I. Korobkov, D. L. Bryce, Cryst. Growth Des. 2012, 12, 1641-1653.
53. L. A. ODell, R. W. Schurko, J. Am. Chem. Soc. 2009, 131, 6658-6659.
54. L. A. ODell, C. I. Ratcliffe, Chem. Commun. 2010, 46, 6774-6776.
55. S. Cavadini, Prog. Nucl. Magn. Reson. Spectrosc. 2010, 56, 46-77.
56. L. A. ODell, Prog. Nucl. Magn. Reson. Spectrosc. 2011, 59, 295-318.
57. C. J. Pickard, F. Mauri, Phys. Rev. B 2001, 63, 245101.
58. F. Mauri, N. Vast, C. J. Pickard, Phys. Rev. Lett. 2001, 87, 085506.
59. M. D. Segall, P. J. D. Lindan, M. J. Probert, C. J. Pickard, P. J. Hasnip, S. J. Clark, M. C. Payne, J. Phys. Condens. Matter 2002, 14, 2717-2744.
60. S. J. Clark, M. D. Segall, C. J. Pickard, P. J. Hasnip, M. I. J. Probert, K. Refson, M. C. Payne, Z. Kristallogr. 2005, 220, 567-570.
61. C. Bonhomme, C. Gervais, F. Babonneau, C. Coelho, F. Pourpoint, T. Azaïs, S. E. Ashbrook, J. M. Griffin, J. R. Yates, F. Mauri, C. J. Pickard, Chem. Rev. 2012, 112, 5733-5779.
62. E. van Lenthe, E. J. Baerends, J. G. Snijders, J. Chem. Phys. 1993, 99, 4597-4610.
63. E. van Lenthe, E. J. Baerends, J. G. Snijders, J. Chem. Phys. 1994, 101, 9783-9792.
64. E. van Lenthe, A. Ehlers, E. J. Baerends, J. Chem. Phys. 1999, 110, 8943-8953.
65. E. van Lenthe, R. van Leeuwen, E. J. Baerends, J. G. Snijders, Int. J. Quantum Chem. 1996, 57, 281-293.
66. A. Abate, M. Brischetto, G. Cavallo, M. Lahtinen, P. Metrangolo, T. Pilati, S. Radice, G. Resnati, K. Rissanen, G. Terraneo, Chem. Commun. 2010, 46, 2724-2726.
67. M. T. Messina, P. Metrangolo, W. Panzeri, E. Ragg, G. Resnati, Tetrahedron Lett. 1998, 39, 9069-9072
68. J. Viger-Gravel, S. Leclerc, I. Korobkov, D. L. Bryce, CrystEngComm 2013, 15, 3168-3177.
69. C. M. Widdifield, D. L. Bryce, J. Phys. Chem. A 2010, 114, 10810-10823.
70. B. Ellman, J. Chem. Phys. 2006, 125, 074702.
71. R. Boese, T. Miebach, CCDC ID code: ZZZPRO05.
72. A. Hinchliffe, R. W. Munn, R. G. Pritchard, C. J. Spicer, J. Mol. Struct. 1985, 130, 93-96.
73. C. M. Widdifield, R. W. Schurko, Concepts Magn. Reson. A 2009, 34, 91-123.
74. M. Bak, J. T. Rasmussen, N. C. Nielsen, J. Magn. Reson. 2000, 147, 296-330.
75. B. Alonso, D. Massiot, P. Florian, H. H. Paradies, P. Gaveau, T. Mineva, J. Phys. Chem. B 2009, 113, 11906-11920.
76. J. Viger-Gravel, I. Korobkov, D. L. Bryce, Cryst. Growth Des. 2011, 11, 4984-4995.
77. E. A. C. Lucken, Nuclear Quadrupole Coupling Constants, Academic, London, 1969.
78. G. K. Semin, T. A. Babushkina, S. P. Khrlakyan, E. Y. Pervova, V. V. Shokina, I. L. Knunyants, Theor. Expt. Chem. 1971, 4, 179-181.
79. C. I. Wynter, J. Hill, W. Bledsoe, G. K. Shenoy, S. L. Ruby, J. Chem. Phys. 1969, 50, 3872-3874.
80. K. J. D. MacKenzie, M. E. Smith, Multinuclear Solid-State NMR of Inorganic Materials, Pergamon, Amsterdam, 2002.
81. M. G. Sarwar, B. Dragisic, L. J. Salsberg, C. Gouliaras, M. S. Taylor, J. Am. Chem. Soc. 2010, 132, 1646-1653.
82. A. L. Webber, B. Elena, J. M. Griffin, J. R. Yates, T. N. Pham, F. Mauri, C. J. Pickard, A. M. Gil, R. Stein, A. Lesage, L. Emsley, S. P. Brown, Phys. Chem. Chem. Phys. 2010, 12, 6970-6983.
83. P. Metrangolo, W. Panzeri, F. Recupero, G. Resnati, J. Fluorine Chem. 2002, 114, 27-33.
84. V. R. Thalladi, H.-C. Weiss, D. Bläser, R. Boese, A. Nangia, G. R. Desiraju, J. Am. Chem. Soc. 1998, 120, 8702-8710.
85. G. Metz, X. Wu, S. O. Smith, J. Magn. Reson. Ser. A 1994, 110, 219-227.
86. A. E. Bennett, C. M. Rienstra, M. Auger, K. V. Lakshmi, R. G. Griffin, J. Chem. Phys. 1995, 103, 6951-6958.
87. B. M. Fung, A. K. Khitrin, K. Ermolaev, J. Magn. Reson. 2000, 142, 97-101.
88. E. L. Hahn, Phys. Rev. 1950, 80, 580-594.
89. S. Hayashi, K. Hayamizu, Bull. Chem. Soc. Jpn. 1991, 64, 685-687.
90. S. Hayashi, K. Hayamizu, Bull. Chem. Soc. Jpn. 1991, 64, 688-690.
91. I. Solomon, Phys. Rev. 1958, 110, 61-65.
92. D. Massiot, I. Farnan, N. Gautier, D. Trumeau, A. Trokiner, J. P. Coutures, Solid State Nucl. Magn. Reson. 1995, 4, 241-248.
93. A. Medek, V. Frydman, L. Frydman, J. Phys. Chem. A 1999, 103, 4830-4835.
94. R. W. Schurko, S. Wi, L. Frydman, J. Phys. Chem. A 2002, 106, 51-62.
95. C. M. Widdifield, D. L. Bryce, J. Phys. Chem. A 2010, 114, 2102-2116.
96. C. M. Widdifield, A. D. Bain, D. L. Bryce, Phys. Chem. Chem. Phys. 2011, 13, 12413-12420.
97. L. A. ODell, R. W. Schurko, K. J. Harris, J. Autschbach, C. I. Ratcliffe, J. Am. Chem. Soc. 2011, 133, 527-546.
98. M. Witanowski, L. Stefaniak, G. A. Webb, Annu. Rep. Nucl. Magn. Reson. Spectrosc. B 1982, 11, 1-486.
99. J. S. Frye, G. E. Maciel, J. Magn. Reson. 1982, 48, 125-131.
100. K. Eichele, R. E. Wasylishen, WSolids1: Solid-State NMR Spectrum Simulation Package, Dalhousie University, Halifax, 2009.
101. J. R. Yates, C. J. Pickard, F. Mauri, Phys. Rev. B 2007, 76, 024401.
102. M. Profeta, F. Mauri, C. J. Pickard, J. Am. Chem. Soc. 2003, 125, 541-548.
103. D. Vanderbilt, Phys. Rev. B 1990, 41, 7892-7895.
104. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868.
105. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1997, 78, 1396.
106. R. P. Chapman, J. R. Hiscock, P. A. Gale, D. L. Bryce, Can. J. Chem. 2011, 89, 822-834.
107. G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. F. Guerra, S. J. A. van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931-937.
108. C. Fonseca Guerra, J. G. Snijders, G. te Velde, E. J. Baerends, Theor. Chem. Acc. 1998, 99, 391-403.
109. SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, ADF v. 2012.01 http://www.scm.com.
110. E. van Lenthe, J. G. Snijders, E. J. Baerends, J. Chem. Phys. 1996, 105, 6505-6516.
111. S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200-1211.
112. Y. Zhang, W. Yang, Phys. Rev. Lett. 1998, 80, 890-890.