Engineering the weak N-H⋯π hydrogen bond in 4-tritylbenzamide host and controlling the interaction through guest selection

CrystEngComm

Volumn 7, Issue , 2005, Pages 44-52

  Malla Reddy, C ^a   Sreenivas Reddy, L ^a   Aitipamula, Srinivasulu ^a   Nangia, Ashwini ^a   Lam, Chi Keung ^b   Mak, Thomas C W ^b  

^a UNIVERSITY OF HYDERABAD   (India)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANISOLE; BENZAMIDE DERIVATIVE; HYDROGEN; NITROGEN;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; ENERGY; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; THERMOGRAVIMETRY; X RAY DIFFRACTION;

EID: 16244378229     PISSN: 14668033     EISSN: None     Source Type: Journal    
DOI: 10.1039/b416985     Document Type: Article

References (37)

1. D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; G. R. Desiraju, Nature, 2001, 412, 397; M. D. Hollingsworth, Science, 2002, 295, 2410; D. Braga, Chem. Commun., 2003, 2751.
2. D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; G. R. Desiraju, Nature, 2001, 412, 397; M. D. Hollingsworth, Science, 2002, 295, 2410; D. Braga, Chem. Commun., 2003, 2751.
3. D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; G. R. Desiraju, Nature, 2001, 412, 397; M. D. Hollingsworth, Science, 2002, 295, 2410; D. Braga, Chem. Commun., 2003, 2751.
4. D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; G. R. Desiraju, Nature, 2001, 412, 397; M. D. Hollingsworth, Science, 2002, 295, 2410; D. Braga, Chem. Commun., 2003, 2751.
5. G. R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
6. T. Steiner, J. H. van der Maas and B. T. G. Lutz, J. Chem. Soc., Perkin Trans. 2, 1997, 1287; B. M. Kariuki, K. D. M. Harris, D. Philip and J. M. A. Robinson, J. Am. Chem. Soc., 1997, 119, 12679; M. G. Davidson, A. E. Goeta, J. A. K. Howard, S. Lamb and S. A. Mason, New J. Chem., 2000, 24, 477; C. K. Broder, M. G. Davidson, V. T. Forsyth, J. A. K. Howard, S. Lamb and S. A. Mason, Cryst. Growth Des., 2002, 2, 163.
7. T. Steiner, J. H. van der Maas and B. T. G. Lutz, J. Chem. Soc., Perkin Trans. 2, 1997, 1287; B. M. Kariuki, K. D. M. Harris, D. Philip and J. M. A. Robinson, J. Am. Chem. Soc., 1997, 119, 12679; M. G. Davidson, A. E. Goeta, J. A. K. Howard, S. Lamb and S. A. Mason, New J. Chem., 2000, 24, 477; C. K. Broder, M. G. Davidson, V. T. Forsyth, J. A. K. Howard, S. Lamb and S. A. Mason, Cryst. Growth Des., 2002, 2, 163.
8. T. Steiner, J. H. van der Maas and B. T. G. Lutz, J. Chem. Soc., Perkin Trans. 2, 1997, 1287; B. M. Kariuki, K. D. M. Harris, D. Philip and J. M. A. Robinson, J. Am. Chem. Soc., 1997, 119, 12679; M. G. Davidson, A. E. Goeta, J. A. K. Howard, S. Lamb and S. A. Mason, New J. Chem., 2000, 24, 477; C. K. Broder, M. G. Davidson, V. T. Forsyth, J. A. K. Howard, S. Lamb and S. A. Mason, Cryst. Growth Des., 2002, 2, 163.
9. T. Steiner, J. H. van der Maas and B. T. G. Lutz, J. Chem. Soc., Perkin Trans. 2, 1997, 1287; B. M. Kariuki, K. D. M. Harris, D. Philip and J. M. A. Robinson, J. Am. Chem. Soc., 1997, 119, 12679; M. G. Davidson, A. E. Goeta, J. A. K. Howard, S. Lamb and S. A. Mason, New J. Chem., 2000, 24, 477; C. K. Broder, M. G. Davidson, V. T. Forsyth, J. A. K. Howard, S. Lamb and S. A. Mason, Cryst. Growth Des., 2002, 2, 163.
10. J. A. Cowan, J. A. C. Clyburne, M. G. Davidson, R. L. W. Harris, J. A. K. Howard, P. Küpper, M. A. Leech and S. P. Richards, Angew. Chem. Int. Ed., 2002, 41, 1432.
11. T. Steiner, Acta Crystallogr., 1998, D54, 584.
12. E. B. Starikov and T. Steiner, Acta Crystallogr., 1998, B54, 94.
13. (a) J. F. Malone, C. M. Murray, M. H. Charlton, R. Docherty and A. J. Lavery, J. Chem. Soc., Faraday Trans., 1997, 93, 3429;
14. (b) D. Braga, F. Grepioni and E. Tedesco, Organometallics, 1998, 17, 2669.
15. C. M. Reddy, A. Nangia, C.-K. Lam and T. C. W. Mak, CrystEngComm, 2002, 4, 323.
16. L. Leiserowitz and G. M. J. Schmidt, J. Chem. Soc. A, 1969, 2372; P. Vishweshwar, A. Nangia and V. M. Lynch, Acta Crystallogr., 2000, C56, 1512; G. T. R. Palmore and J. C. MacDonald, in The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science, ed. A. Greenberg, C. M. Breneman and J. F. Liebman, John Wiley, Chichester, 2000, pp. 291-336.
17. L. Leiserowitz and G. M. J. Schmidt, J. Chem. Soc. A, 1969, 2372; P. Vishweshwar, A. Nangia and V. M. Lynch, Acta Crystallogr., 2000, C56, 1512; G. T. R. Palmore and J. C. MacDonald, in The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science, ed. A. Greenberg, C. M. Breneman and J. F. Liebman, John Wiley, Chichester, 2000, pp. 291-336.
18. L. Leiserowitz and G. M. J. Schmidt, J. Chem. Soc. A, 1969, 2372; P. Vishweshwar, A. Nangia and V. M. Lynch, Acta Crystallogr., 2000, C56, 1512; G. T. R. Palmore and J. C. MacDonald, in The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science, ed. A. Greenberg, C. M. Breneman and J. F. Liebman, John Wiley, Chichester, 2000, pp. 291-336.
19. R. K. R. Jetti, F. Xue, T. C. W. Mak and A. Nangia, J. Chem. Soc., Perkin Trans. 2, 2000, 1223.
20. T. Steiner and S. Mason, Acta Crystallogr., 2000, B56, 254; S. George, A. Nangia and V. M. Lynch, Acta Crystallogr., 2001, C57, 777.
21. T. Steiner and S. Mason, Acta Crystallogr., 2000, B56, 254; S. George, A. Nangia and V. M. Lynch, Acta Crystallogr., 2001, C57, 777.
22. T. Müller, J. Hulliger, W. Seichter, E. Weber, T. Weber and M. A. Wübbenjorst, Chem. Eur. J., 2000, 6, 54; Z. Dominguez, H. Dang, M. J. Strouse and M. A. Garcia-Garibay, J. Am. Chem. Soc., 2002, 124, 7719; J. Overgaard, B. B. Iverson, S. P. Palii, G. A. Timco, N. V. Gerbeleu and F. K. Larsen, Chem. Eur. J., 2002, 8, 2775; D. V. Soldatov, I. L. Moudrakovski, C. I. Ratcliffe, R. Dutrisac and J. A. Ripmester, Chem. Mater., 2003, 15, 4810; A. Bacchi, E. Bosetti, M. Carcelli, P. Pelagatti and D. Rogolino, CrystEngComm, 2004, 6, 177.
23. T. Müller, J. Hulliger, W. Seichter, E. Weber, T. Weber and M. A. Wübbenjorst, Chem. Eur. J., 2000, 6, 54; Z. Dominguez, H. Dang, M. J. Strouse and M. A. Garcia-Garibay, J. Am. Chem. Soc., 2002, 124, 7719; J. Overgaard, B. B. Iverson, S. P. Palii, G. A. Timco, N. V. Gerbeleu and F. K. Larsen, Chem. Eur. J., 2002, 8, 2775; D. V. Soldatov, I. L. Moudrakovski, C. I. Ratcliffe, R. Dutrisac and J. A. Ripmester, Chem. Mater., 2003, 15, 4810; A. Bacchi, E. Bosetti, M. Carcelli, P. Pelagatti and D. Rogolino, CrystEngComm, 2004, 6, 177.
24. T. Müller, J. Hulliger, W. Seichter, E. Weber, T. Weber and M. A. Wübbenjorst, Chem. Eur. J., 2000, 6, 54; Z. Dominguez, H. Dang, M. J. Strouse and M. A. Garcia-Garibay, J. Am. Chem. Soc., 2002, 124, 7719; J. Overgaard, B. B. Iverson, S. P. Palii, G. A. Timco, N. V. Gerbeleu and F. K. Larsen, Chem. Eur. J., 2002, 8, 2775; D. V. Soldatov, I. L. Moudrakovski, C. I. Ratcliffe, R. Dutrisac and J. A. Ripmester, Chem. Mater., 2003, 15, 4810; A. Bacchi, E. Bosetti, M. Carcelli, P. Pelagatti and D. Rogolino, CrystEngComm, 2004, 6, 177.
25. T. Müller, J. Hulliger, W. Seichter, E. Weber, T. Weber and M. A. Wübbenjorst, Chem. Eur. J., 2000, 6, 54; Z. Dominguez, H. Dang, M. J. Strouse and M. A. Garcia-Garibay, J. Am. Chem. Soc., 2002, 124, 7719; J. Overgaard, B. B. Iverson, S. P. Palii, G. A. Timco, N. V. Gerbeleu and F. K. Larsen, Chem. Eur. J., 2002, 8, 2775; D. V. Soldatov, I. L. Moudrakovski, C. I. Ratcliffe, R. Dutrisac and J. A. Ripmester, Chem. Mater., 2003, 15, 4810; A. Bacchi, E. Bosetti, M. Carcelli, P. Pelagatti and D. Rogolino, CrystEngComm, 2004, 6, 177.
26. T. Müller, J. Hulliger, W. Seichter, E. Weber, T. Weber and M. A. Wübbenjorst, Chem. Eur. J., 2000, 6, 54; Z. Dominguez, H. Dang, M. J. Strouse and M. A. Garcia-Garibay, J. Am. Chem. Soc., 2002, 124, 7719; J. Overgaard, B. B. Iverson, S. P. Palii, G. A. Timco, N. V. Gerbeleu and F. K. Larsen, Chem. Eur. J., 2002, 8, 2775; D. V. Soldatov, I. L. Moudrakovski, C. I. Ratcliffe, R. Dutrisac and J. A. Ripmester, Chem. Mater., 2003, 15, 4810; A. Bacchi, E. Bosetti, M. Carcelli, P. Pelagatti and D. Rogolino, CrystEngComm, 2004, 6, 177.
27. B. T. G. Lutz, J. Jacob and J. H. van der Maas, Vib. Spectrosc., 1996, 12, 197.
28. K. Uemura, S. Kitagawa, M. Kondo, K. Fukui, R. Kitaura, H.-C. Chang and T. Mizutani, Chem. Eur. J., 2002, 8, 3587.
29. For recent examples of host showing guest inclusion in different cavities, see: S. Apel, M. Czugler, V. J. Griffith, L. R. Nassimbeni and E. Weber, J. Chem. Soc., Perkin Trans. 2, 1997, 1949; R. Bishop, A. N. M. M. Rahman, J. Ashmore, D. C. Craig and M. L. Scudder, CrystEngComm, 2002, 4, 605.
30. For recent examples of host showing guest inclusion in different cavities, see: S. Apel, M. Czugler, V. J. Griffith, L. R. Nassimbeni and E. Weber, J. Chem. Soc., Perkin Trans. 2, 1997, 1949; R. Bishop, A. N. M. M. Rahman, J. Ashmore, D. C. Craig and M. L. Scudder, CrystEngComm, 2002, 4, 605.
31. Calculated in CERIUS2, http://www.accelrys.com. Single point lattice energies with no relaxation of atomic distances and angles compared to the crystal structure gave similar trends in energies. We prefer to compute optimized crystal energies.
32. L. R. Nassimbeni, Acc. Chem. Res., 2003, 36, 631.
33. SHELXS-97: G. M. Sheldrick, Program for the Solution of Crystal Structures,University of Göttingen, Germany, 1997SHELXL-97: G. M. Sheldrick, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
34. SHELXS-97: G. M. Sheldrick, Program for the Solution of Crystal Structures,University of Göttingen, Germany, 1997SHELXL-97: G. M. Sheldrick, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
35. SADABS: G. M. Sheldrick, Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, Germany, 1996; G. M. Sheldrick, Program for Multi-Scan Absorption Correction of Area Detector Data (version 2.10), University of Göttingen, Germany, 2003.
36. SADABS: G. M. Sheldrick, Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, Germany, 1996; G. M. Sheldrick, Program for Multi-Scan Absorption Correction of Area Detector Data (version 2.10), University of Göttingen, Germany, 2003.
37. SHELXTL (version 6.14) Bruker AXS, Program for the Solution and Refinement of Crystal Structures, Wisconsin, USA, 2000.