Synthesis of a preorganized hybrid macrobicycle with distinct amide and amine clefts: Tetrahedral versus spherical anions binding studies

Journal of Organic Chemistry

Volumn 78, Issue 17, 2013, Pages 8759-8765

  Saha, Subrata ^a   Akhuli, Bidyut ^a   Chakraborty, Sourav ^a   Ghosh, Pradyut ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANION RECOGNITION; ASSOCIATION CONSTANT; CONFORMATIONAL ANALYSIS; ISOTHERMAL TITRATION CALORIMETERS; PROTONATED STATE; SINGLE CRYSTAL X-RAY STRUCTURES; SOLID-STATE STRUCTURES; TETRAHEDRAL ANION;

AMIDES; ENTROPY; PROTONATION; SPHERES;

NEGATIVE IONS;

AMIDE; AMINE; AMMONIA; ANION; BICYCLO COMPOUND; BROMINE; CHLORIDE; DIMETHYL SULFOXIDE; HALIDE; METHANOL; PHENYL GROUP; SULFATE;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL STRUCTURE; ENTHALPY; ENTROPY; HYBRID; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR RECOGNITION; NUCLEAR OVERHAUSER EFFECT; PROTON TRANSPORT; REACTION ANALYSIS; SOLID STATE; SYNTHESIS;

AMIDES; AMINES; ANIONS; CRYSTALLOGRAPHY, X-RAY; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 84883811114     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401504f     Document Type: Article

References (61)

1. Bianchi, A., Bowman-James, K., Garcia-Espana, E., Eds. Supramolecular Chemistry of Anions; Wiley-VCH: New York, 1997.
2. Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry; Royal Society of Chemistry, London, 2006.
3. Schneider, H.-J. Fundam. Appl. Anion Sep., [Proc. Symp. Am. Chem. Soc. Natl. Meet.] 2004, 31-42
4. Wenzel, M.; Hiscock, J. R.; Gale, P. A. Chem. Soc. Rev. 2012, 41, 480-520
5. Dydio, P.; Lichosyt, D.; Jurczak, J. Chem. Soc. Rev. 2011, 40, 2971-2985
6. Mullen, K. M.; Beer, P. D. Chem. Soc. Rev. 2009, 38, 1701-1713
7. Bowman-James, K. Acc. Chem. Res. 2005, 38, 671-678
8. Pflugrath, J. W.; Quiocho, F. A. Nature (London) 1985, 314, 257-260
9. Bowman-James, K.; Bianchi, A.; Garcia-Espana, E., Eds. Anion Coordination Chemistry; Wiley-VCH: New York, 2012.
10. Park, C. H.; Simmons, H. E. J. Am. Chem. Soc. 1968, 90, 2431-2432
11. Kang, S.-O.; Llinares, J. M.; Day, V. W.; Bowman-James, K. Chem. Soc. Rev. 2010, 39, 3980-4003
12. Hossain, A.; Kang, S. O.; Bowman-James, K.; Springer: New York, 2005; pp 173-188.
13. Perraud, O.; Robert, V.; Martinez, A.; Dutasta, J.-P. Chem.-Eur. J. 2011, 17, 13405-13408
14. Young, P. G.; Clegg, J. K.; Bhadbhade, M.; Jolliffe, K. A. Chem. Commun. (Cambridge, U. K.) 2011, 47, 463-465
15. McKee, V.; Nelson, J.; Town, R. M. Chem. Soc. Rev. 2003, 32, 309-325
16. Ballester, P. Chem. Soc. Rev. 2010, 39, 3810-3830
17. Bucher, C.; Zimmerman, R. S.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 2001, 123, 9716-9717
18. Dietrich, B.; Guilhem, J.; Lehn, J. M.; Pascard, C.; Sonveaux, E. Helv. Chim. Acta 1984, 67, 91-104
19. Ilioudis, C. A.; Tocher, D. A.; Steed, J. W. J. Am. Chem. Soc. 2004, 126, 12395-12402
20. Mateus, P.; Delgado, R.; Brandao, P.; Felix, V. Org. Biomol. Chem. 2012, 10, 5529-5532
21. Mateus, P.; Delgado, R.; Brandao, P.; Felix, V. J. Org. Chem. 2012, 77, 4611-4621
22. Mateus, P.; Delgado, R.; Brandao, P.; Carvalho, S.; Felix, V. Org. Biomol. Chem. 2009, 7, 4661-4673
23. Saeed, M. A.; Fronczek, F. R.; Hossain, M. A. Chem. Commun. (Cambridge, U. K.) 2009, 6409-6411
24. Llinares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57-75
25. Das, M. C.; Ghosh, S. K.; Bharadwaj, P. K. Dalton Trans. 2009, 6496-6506
26. Dietrich, B.; Lehn, J. M.; Guilhem, J.; Pascard, C. Tetrahedron Lett. 1989, 30, 4125-4128
27. Saeed, M. A.; Fronczek, F. R.; Huang, M.-J.; Hossain, M. A. Chem. Commun. (Cambridge, U. K.) 2010, 46, 404-406
28. Wichmann, K.; Antonioli, B.; Soehnel, T.; Wenzel, M.; Gloe, K.; Gloe, K.; Price, J. R.; Lindoy, L. F.; Blake, A. J.; Schroeder, M. Coord. Chem. Rev. 2006, 250, 2987-3003
29. Lakshminarayanan, P. S.; Kumar, D. K.; Ghosh, P. Inorg. Chem. 2005, 44, 7540-7546
30. Chakraborty, S.; Arunachalam, M.; Bose, P.; Ghosh, P. Cryst. Growth Des. 2013, 13, 3208-3215
31. Kang, S. O.; Begum, R. A.; Bowman-James, K. Angew. Chem., Int. Ed. 2006, 45, 7882-7894
32. Kang, S. O.; Llinares, J. M.; Powell, D.; VanderVelde, D.; Bowman-James, K. J. Am. Chem. Soc. 2003, 125, 10152-10153
33. Kang, S. O.; Day, V. W.; Bowman-James, K. J. Org. Chem. 2010, 75, 277-283
34. Kang, S. O.; Powell, D.; Bowman-James, K. J. Am. Chem. Soc. 2005, 127, 13478-13479
35. Bisson, A. P.; Lynch, V. M.; Monahan, M.-K. C.; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 2340-2342
36. Nelson, J.; Nieuwenhuyzen, M.; Pal, I.; Town, R. M. Dalton Trans. 2004, 2303-2308
37. Kaewtong, C.; Fuangswasdi, S.; Muangsin, N.; Chaichit, N.; Vicens, J.; Pulpoka, B. Org. Lett. 2006, 8, 1561-1564
38. Kang, S. O.; Powell, D.; Day, V. W.; Bowman-James, K. Angew. Chem., Int. Ed. 2006, 45, 1921-1925
39. Ravikumar, I.; Lakshminarayanan, P. S.; Suresh, E.; Ghosh, P. Inorg. Chem. (Washington, DC, U. S.) 2008, 47, 7992-7999
40. Mateus, P.; Delgado, R.; Brandao, P.; Felix, V. Chem.-Eur. J. 2011, 17, 7020-7031
41. Ghosh, P.; Gupta, S. S.; Bharadwaj, P. K. J. Chem. Soc., Dalton Trans. 1997, 935-938
42. Chand, D. K.; Bharadwaj, P. K. Inorg. Chem. 1996, 35, 3380-3387
43. Mahoney, J. M.; Stucker, K. A.; Jiang, H.; Carmichael, I.; Brinkmann, N. R.; Beatty, A. M.; Noll, B. C.; Smith, B. D. J. Am. Chem. Soc. 2005, 127, 2922-2928
44. Chand, D. K.; Bharadwaj, P. K. Inorg. Chem. 1998, 37, 5050-5055
45. Chae, M. K.; Lee, J.-I.; Kim, N.-K.; Jeong, K.-S. Tetrahedron Lett. 2007, 48, 6624-6627
46. Turner, D. R.; Paterson, M. J.; Steed, J. W. J. Org. Chem. 2006, 71, 1598-1608
47. Steed, J. W. Chem. Commun. (Cambridge, U. K.) 2006, 2637-2649
48. Arunachalam, M.; Ghosh, P. Chem. Commun. (Cambridge, U. K.) 2011, 47, 8477-8492
49. Bose, P.; Ravikumar, I.; Ghosh, P. Inorg. Chem. 2011, 50, 10693-10702
50. Hossain, M. A.; Liljegren, J. A.; Powell, D.; Bowman-James, K. Inorg. Chem. 2004, 43, 3751-3755
51. Lakshminarayanan, P. S.; Ravikumar, I.; Suresh, E.; Ghosh, P. Inorg. Chem. 2007, 46, 4769-4771
52. Sessler, J. L.; Gross, D. E.; Cho, W.-S.; Lynch, V. M.; Schmidtchen, F. P.; Bates, G. W.; Light, M. E.; Gale, P. A. J. Am. Chem. Soc. 2006, 128, 12281-12288
53. Krause, M. R.; Goddard, R.; Kubik, S. J. Org. Chem. 2011, 76, 7084-7095
54. Nativi, C.; Cacciarini, M.; Francesconi, O.; Vacca, A.; Moneti, G.; Ienco, A.; Roelens, S. J. Am. Chem. Soc. 2007, 129, 4377-4385
55. SAINT and XPREP, 5.1 ed.; Siemens Industrial Automation Inc.: Madison, WI, 1995. Sheldrick, G. M.
56. SADABS, empirical absorption Correction Program; University of Göttingen: Göttingen, Germany, 1997.
57. Sheldrick, G. M. SHELXTL Reference Manual, Version 5.1; Bruker AXS: Madison, WI, 1997.
58. Sheldrick, G. M. SHELXL-97: Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
59. Spek, A. L. PLATON-97; University of Utrecht: Utrecht, The Netherlands, 1997.
60. Mercury 2.3, Supplied with Cambridge Structural Database; CCDC: Cambridge, U.K., 2003-2004.
61. van der Sluis, P.; Spek, A. L. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, A46, 194-201