C-H⋯Br, C-Br⋯Br, and C-Br⋯π interactions in the crystal structures of mesitylene- and dimesitylmethane-derived compounds bearing bromomethyl units

Tetrahedron

Volumn 66, Issue 1, 2010, Pages 385-389

  Mazik, Monika ^a   Buthe, Arno C ^a   Jones, Peter G ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Crystal engineering; Halogen bonds; Hydrogen bonds; Noncovalent interactions; Supramolecular chemistry

Indexed keywords

1,3,5 TRIMETHYLBENZENE; BROMINE DERIVATIVE; DIMESITYLMETHANE; METHANE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; MOLECULAR INTERACTION; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 70549109019     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.067     Document Type: Article

References (59)

1. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford University, Oxford
2. Desiraju G.R. Chem. Commun. (2005) 2995-3001
3. For examples of CH⋯O hydrogen bonds, see Ref. 1a,b, 2a and:
4. Castellano R.K. Curr. Org. Chem. 8 (2004) 845-865
5. Steiner T. J. Chem. Soc., Chem. Commun. (1994) 2341-2342
6. Steiner T., and Desiraju G.R. Chem. Commun. (1998) 891-892
7. Steiner T. Chem. Commun. (1997) 727-734
8. Novoa J.J., Lafuente P., and Mota F. Chem. Phys. Lett. 290 (1998) 519-525
9. Braga D., and Grepioni F. New J. Chem. (1998) 1159-1161
10. Desiraju G.R. Acc. Chem. Res. 29 (1997) 441-449
11. Klaholz B.P., and Moras D. Structure 10 (2002) 1197-1204
12. Forristal I., Lowman J., Afarinkia K., and Steed J.W. CrystEngComm. 3 (2001) 53-56
13. Alshahateet S.F., Bishop R., Craig D.C., and Scudder M.L. CrystEngComm 3 (2001) 107-110
14. Mazik M., Bläser D., and Boese R. J. Org. Chem. 70 (2005) 9115-9122
15. Mazik M., Bläser D., and Boese R. Tetrahedron 55 (1999) 12771-12782
16. For examples of CHċN hydrogen bonds, see Ref. 1a and:
17. Taylor R., and Kennard O. J. Am. Chem. Soc. 104 (1982) 5063-5070
18. Mazik M., Bläser D., and Boese R. Tetrahedron Lett. 41 (2000) 5827-5831
19. Mazik M., Bläser D., and Boese R. Tetrahedron 57 (2001) 5791-5797
20. Thalladi V.R., Gehrke A., and Boese R. New J. Chem. (2000) 463-470
21. Thalladi V.R., Smolka T., Gehrke A., Boese R., and Sustmann R. New J. Chem. 24 (2000) 143-147
22. Desiraju G.R. Crystal Engineering. The Design of Organic Solids (1989), Elsevier, Amsterdam pp. 166-167
23. Mazik M., Bläser D., and Boese R. Tetrahedron 55 (1999) 7835-7840
24. Mazik M., Bläser D., and Boese R. Chem.-Eur. J. 6 (2000) 2865-2873
25. For a discussion on CHċhalogen interactions, see:. Aakeröy C.B., Evans T.A., Seddon K.R., and Pálinkó I. New. J. Chem. (1999) 145-152
26. For examples of C-Hċhalogen and halogenċhalogen interaction, see Ref. 2k,3a,12, and:
27. Reddy D.S., Craig D.C., and Desiraju G.R. J. Am. Chem. Soc. 118 (1996) 4090-4093
28. Rahman A.N.M.M., Bishop R., Craig D.C., and Scudder M.L. Org. Biomol. Chem. 2 (2004) 175-182
29. Rahman A.N.M.M., Bishop R., Craig D.C., and Scudder M.L. Org. Biomol. Chem. 1 (2003) 1435-1441
30. Spaniel T., Görls H., and Scholz J. Angew. Chem., Int. Ed. 36 (1997) 601-603
31. SpanielT, GörlsH, and ScholzJ. Angew. Chem., Int. Ed. 37 (1998) 1862-1865
32. Hartmann M., Wetmore S.D., and Radom L. J. Phys. Chem. A 105 (2001) 4470-4479
33. Swierczynski D., Luboradzki R., Dolgonos G., Lipkowski J., and Schneider H.-J. Eur. J. Org. Chem. (2005) 1172-1177
34. Jones P.G., and Kuś P. Z. Naturforsch. 62b (2007) 725-731
35. Jones P.G., Zemanek A., and Kuś P. Acta Crystallogr., Sect. C 63 (2007) o73-o76
36. Rosokha S.V., Neretin I.S., Rosokha T.Y., Hecht J., and Kochi J.K. Heteroat. Chem. 17 (2006) 449-459
37. For reviews on halogen bonding, see:
38. Metrangolo P., Neukirch H., Pilati T., and Resnati G. Acc. Chem. Res. 38 (2005) 386-395
39. Metrangolo P., Meyer F., Pilati T., Resnati G., and Terraneo G. Angew. Chem., Int. Ed. 47 (2008) 6114-6127
40. In: Metrangolo P., and Resnati G. (Eds). Halogen Bonding Fundamentals and Applications (2008), Springer, Berlin
41. Rissanen K. CrystEngComm. 10 (2008) 1107-1113
42. Van der Made A.W., and van der Made R.H. J. Org. Chem. 58 (1993) 1262-1263
43. Mazik M., and Buthe A.C. Org. Biomol. Chem. 7 (2009) 2063-2071
44. Mazik M. Chem. Soc. Rev. 38 (2009) 935-956
45. Mazik M., and Buthe A.C. J. Org. Chem. 72 (2007) 8319-8326
46. Mazik M., and Cavga H. J. Org. Chem. 71 (2006) 2957-2963
47. Mazik M., Cavga H., and Jones P.G. J. Am. Chem. Soc. 127 (2005) 9045-9052
48. Mazik M., Radunz W., and Boese R. J. Org. Chem. 69 (2004) 7448-7462
49. Mazik M., Radunz W., and Sicking W. Org. Lett. 4 (2002) 4579-4582
50. The crystal structure of the mesitylene derivative 1 was reported by J.-A. Gertenbach et al. (crystals were grown from 1,2-dichloroethane; see Ref. 10b); however, without a detailed analysis of the packing motifs. We have included the data for comparison with the crystal packing of the dimesitylmethane derivatives 2 and 3. Our analysis was carried out on the basis of an independent crystal structure of 1 (crystals were grown from acetonitrile, but represent the same modification), which was obtained by us without knowledge of Ref. 10b.
51. Murray P., Willans C., Bredenkamp M.W., and Gertenbach J.-A. Acta Crystallogr., Sect. E 63 (2007) o224-o225
52. Bondi A. J. Phys. Chem. 68 (1964) 441-451
53. Pedireddi V.R., Reddy D.S., Goud B.S., Craig D.C., Rae A.D., and Desiraju G.R. J. Chem. Soc., Perkin Trans. 2 (1994) 2353-2360
54. Jeffrey G.A. An Introduction to Hydrogen Bonding (1997), Oxford University, New York, NY
55. Jeffrey G.A., and Saenger W. Hydrogen Bonding in Biological Structures (1994), Springer-Verlag, Berlin
56. Steiner T. Angew. Chem., Int. Ed. 41 (2002) 48-76
57. Legon A.C. Angew. Chem., Int. Ed. 38 (1999) 2686
58. Rosokha S.V., and Kochi J.K. In: Metrangolo P., and Resnati G. (Eds). Halogen Bonding Fundamentals and Applications (2008), Springer, Berlin 137-160 and references therein
59. Sheldrick G.M. Acta Crystallogr., Sect. A 64 (2008) 112-122