Utilizing Sulfoxide···Iodine Halogen Bonding for Cocrystallization
Source abstract
Abstract
The propensity of a range of different sulfoxides and sulfones to cocrystallize with either 1,2- or 1,4-diiodotetrafluorobenzene, via I···O=S halogen bonding, was investigated. Cocrystallization occurred exclusively with 1,4-diiodotetrafluorobenzene in either a 1:1 or 1:2 stoichiometry of the organohalide and the sulfoxide, respectively, depending on the sulfoxide used. It was found that the stoichiometry observed was not necessarily related to whether the oxygen acts as a single halogen bond acceptor or if it is bifurcated; with I···π interactions observed in two of the cocrystals synthesized. Only those cocrystals with a 1:2 stoichiometry exhibit C–H···O hydrogen bonding in addition to I···O=S halogen bonding. Examination of the Cambridge Structural Database shows that (i) the I···O=S interaction is similar to other I···O interactions, and (ii) the I···π interaction is significant, with the distances in the two cocrystals among the shortest known.
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: Crystallography and molecular interactions · Crystallization and Solubility Studies · Crystal structures of chemical compounds
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
School of Pharmacy, University of East Anglia, Norwich Research Park, Norwich NR4 7TJ, U.K.
Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
References (55)
Show source-provided references
1. Trask A. V. · Mol. Pharmaceutics · 2007 · 4 · 30110.1021/mp070001z ↗
2. Shan N. · Drug Discovery Today · 2008 · 13 · 44010.1016/j.drudis.2008.03.004 ↗
3. Aakeröy C. B. · CrystEngComm · 2005 · 7 · 43910.1039/b505883j ↗
4. Stahly G. P. · Cryst. Growth Des. · 2009 · 9 · 421210.1021/cg900873t ↗
5. Fábián L. · Cryst. Growth Des. · 2009 · 9 · 143610.1021/cg800861m ↗
6. Trask A. V. · Top. Curr. Chem. · 2005 · 254 · 4110.1007/b100995 ↗
7. Weyna D. R. · Cryst. Growth Des. · 2009 · 9 · 110610.1021/cg800936d ↗
8. Trask A. V. · Chem. Commun. · 2004 · 89010.1039/b400978a ↗
9. McCausland, L.PCT Int. Appl. WO2007075793, 2007.
10. Rissanen K. · CrystEngComm · 2008 · 10 · 110710.1039/b803329n ↗
11. Metrangolo P. · Acc. Chem. Res. · 2005 · 38 · 38610.1021/ar0400995 ↗
12. Sarma J. A. R. P. · Chem. Commun. · 1997 · 10110.1039/a605044a ↗
13. Thallapally P. K. · Chem. Commun. · 2002 · 105210.1039/b201224c ↗
14. Chopra D. · Cryst. Growth Des. · 2012 · 12 · 54110.1021/cg201498u ↗
15. Chopra D. · J. Mol. Struct. · 2008 · 888 · 7010.1016/j.molstruc.2007.11.040 ↗
16. Thakur T. S. · CrystEngComm · 2010 · 207910.1039/b925082d ↗
17. Dikundwar A. G. · Cryst. Growth Des. · 2012 · 12 · 171310.1021/cg3002477 ↗
18. Weiss R. · Chem.—Eur. J. · 1999 · 5 · 96810.1002/(SICI)1521-3765(19990301)5:3<968::AID-CHEM968>3.0.CO;2-L ↗
19. Aakeröy C. B. · Cryst. Growth Des. · 2009 · 9 · 43210.1021/cg8006712 ↗
20. Eccles K. S. · Cryst. Growth Des. · 2010 · 10 · 424310.1021/cg1010192 ↗
21. Eccles K. S. · Cryst. Growth Des. · 2011 · 11 · 443310.1021/cg2006277 ↗
22. Arman H. D. · Chem. Commun. · 2010 · 46 · 185410.1039/B925710A ↗
23. Cinčić D. · Chem.—Eur. J. · 2008 · 14 · 74710.1002/chem.200701184 ↗
24. Allen F. H. · Acta Crystallogr. · 2002 · 58 · 38010.1107/S0108768102003890 ↗
25. Britton D. · Acta Crystallogr. · 2003 · 59 · o1332
26. Xu H. J. · Synlett · 2008 · 19 · 3063
27. Eccles K. S. · ARKIVOC · 2010 · 21610.3998/ark.5550190.0011.921 ↗
28. Hirano M. · Bull. Chem. Soc. Jpn. · 1991 · 64 · 375210.1246/bcsj.64.3752 ↗
29. Drabowicz J. · J. Org. Chem. · 1982 · 47 · 332510.1021/jo00138a026 ↗
30. Gilman H. · J. Am. Chem. Soc. · 1955 · 77 · 338710.1021/ja01617a072 ↗
31. Eccles K. S. · J. Appl. Crystallogr. · 2011 · 44 · 21310.1107/S0021889810042561 ↗
32. APEX2 v2009.3-0;Bruker AXS: 2009.
33. Sheldrick G. M. · Acta Crystallogr. · 2008 · 64 · 11210.1107/S0108767307043930 ↗
34. Macrae C. F. · J. Appl. Crystallogr. · 2008 · 41 · 46610.1107/S0021889807067908 ↗
35. Bruno I. J. · Acta Crystallogr. · 2002 · 58 · 38910.1107/S0108768102003324 ↗
36. 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, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; 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, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J.Gaussian 09, Revision B.1;Gaussian, Inc.:Wallingford, CT, 2009.
37. Zhao Y. · Theor. Chem. Acc. · 2008 · 120 · 21510.1007/s00214-007-0310-x ↗
38. Check C. E. · J. Phys. Chem. A · 2001 · 105 · 811110.1021/jp011945l ↗
39. Schuchardt K. L. · J. Chem. Inf. Model. · 2007 · 47 · 104510.1021/ci600510j ↗
40. NBO Version 3.1.Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.
41. Cinčić D. · CrystEngComm · 2011 · 13 · 322410.1039/c0ce00699h ↗
42. Schultheiss N. · Cryst. Growth Des. · 2009 · 9 · 295010.1021/cg900129f ↗
43. Syssa-Magalé J. L. · CrystEngComm · 2005 · 7 · 30210.1039/B500009B ↗
44. Oae S. · J. Am. Chem. Soc. · 1960 · 82 · 535910.1021/ja01505a022 ↗
45. Noguchi Y. · Bull. Chem. Soc. Jpn. · 1983 · 56 · 34910.1246/bcsj.56.349 ↗
46. Meyers C. Y. · Gazz. Chim. Ital. · 1963 · 93 · 1206
47. Goud N. R. · Cryst. Growth Des. · 2011 · 11 · 193010.1021/cg200094x ↗
48. Casarini D. · Angew. Chem., Int. Ed. · 2001 · 40 · 253610.1002/1521-3773(20010702)40:13<2536::AID-ANIE2536>3.0.CO;2-R ↗
49. Hosoya S. · Chem. Ind. (London) · 1957 · 1042
50. Bonchio M. · J. Org. Chem. · 1995 · 60 · 447510.1021/jo00119a026 ↗
51. Bissantz C. · J. Med. Chem. · 2010 · 53 · 506110.1021/jm100112j ↗
52. Brondel N. · CrystEngComm · 2010 · 12 · 291010.1039/c000371a ↗
53. Fuller A. L. · J. Chem. Crystallogr. · 2009 · 39 · 40710.1007/s10870-008-9493-9 ↗
54. Zeng Y. X. · Acta Crystallogr. · 2011 · 67 · o177
55. Anderson K. M. · Cryst. Growth Des. · 2008 · 8 · 251710.1021/cg8001527 ↗