Supramolecular equivalence of halogen, ethynyl and hydroxy groups. A comparison of the crystal structures of some 4-substituted anilines

CrystEngComm

Volumn 5, Issue , 2003, Pages 248-252

  Dey, Archan ^a   Jetti, Ram K R ^b   Boese, Roland ^b   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; HALOGEN; HYDROXYL GROUP;

ANALYTIC METHOD; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CRYSTAL STRUCTURE; GEOMETRY; POLARIZATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 15944416474     PISSN: 14668033     EISSN: None     Source Type: Journal    
DOI: 10.1039/b304785g     Document Type: Article

References (42)

1. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
2. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
3. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
4. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
5. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
6. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
7. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
8. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
9. G. R. Desiraju, Stimulating Concepts in Chemistry, eds. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 293; A. Nangia and G. R. Desiraju, Top. Curr. Chem., 1998, 198, 57; D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, CrystEngComm, 2002, 4, 500; J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530; J.-H. Fournier, T. Maris, J. D. Wuest, W. Guo and E. Galoppini, J. Am. Chem. Soc., 2003, 125, 1002; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, J. Am. Chem. Soc., 2002, 124, 14425; C. B. Aakeröy, A. M. Beatty and B. A. Helfrich, Angew. Chem., Int. Ed., 2002, 40, 3240; S. Hanessian, R. Saladino, R. Margarita and M. Simard, Chem. Eur. J., 1999, 5, 2169; P. Vishweshwar, A. Nangia and V. M. Lynch, J. Org. Chem., 2002, 67, 55.
10. Selected references include: R. J. Davey, K. Allen, N. Blagden, W. I. Cross, H. F. Lieberman, M. J. Quayle, S. Righini, L. Seton and G. J. T. Tiddy, CrystEngComm, 2002, 4, 257; J. A. R. P. Sarma and G. R. Desiraju, Cryst. Growth. Des., 2002, 2, 93; B. R. Bhogala, P. Vishweshwar and A. Nangia, Cryst. Growth. Des., 2002, 2, 325; P. K. Thallapally, A. K. Katz, H. L. Carrell and G. R. Desiraju, Chem. Commun., 2002, 344.
11. Selected references include: R. J. Davey, K. Allen, N. Blagden, W. I. Cross, H. F. Lieberman, M. J. Quayle, S. Righini, L. Seton and G. J. T. Tiddy, CrystEngComm, 2002, 4, 257; J. A. R. P. Sarma and G. R. Desiraju, Cryst. Growth. Des., 2002, 2, 93; B. R. Bhogala, P. Vishweshwar and A. Nangia, Cryst. Growth. Des., 2002, 2, 325; P. K. Thallapally, A. K. Katz, H. L. Carrell and G. R. Desiraju, Chem. Commun., 2002, 344.
12. Selected references include: R. J. Davey, K. Allen, N. Blagden, W. I. Cross, H. F. Lieberman, M. J. Quayle, S. Righini, L. Seton and G. J. T. Tiddy, CrystEngComm, 2002, 4, 257; J. A. R. P. Sarma and G. R. Desiraju, Cryst. Growth. Des., 2002, 2, 93; B. R. Bhogala, P. Vishweshwar and A. Nangia, Cryst. Growth. Des., 2002, 2, 325; P. K. Thallapally, A. K. Katz, H. L. Carrell and G. R. Desiraju, Chem. Commun., 2002, 344.
13. Selected references include: R. J. Davey, K. Allen, N. Blagden, W. I. Cross, H. F. Lieberman, M. J. Quayle, S. Righini, L. Seton and G. J. T. Tiddy, CrystEngComm, 2002, 4, 257; J. A. R. P. Sarma and G. R. Desiraju, Cryst. Growth. Des., 2002, 2, 93; B. R. Bhogala, P. Vishweshwar and A. Nangia, Cryst. Growth. Des., 2002, 2, 325; P. K. Thallapally, A. K. Katz, H. L. Carrell and G. R. Desiraju, Chem. Commun., 2002, 344.
14. T. Steiner, J. Chem. Soc. Chem. Commun., 1995, 95.
15. H.-C. Weiss, R. Boese, H. L. Smith and M. M. Haley, Chem. Commun., 1997, 2403.
16. J. M. A. Robinson, B. M. Kariuki, K. D. M. Harris and D. Philp, J. Chem. Soc., Perkin Trans. 2, 1998, 2459.
17. E. Gallopini and R. Gilardi, J. Chem. Soc., Chem. Commun., 1999, 173; W. Guo, E. Galoppini, R. Gilardi, G. I. Rydja and Y.-H. Chen, Cryst. Growth Des., 2001, 1, 231.
18. E. Gallopini and R. Gilardi, J. Chem. Soc., Chem. Commun., 1999, 173; W. Guo, E. Galoppini, R. Gilardi, G. I. Rydja and Y.-H. Chen, Cryst. Growth Des., 2001, 1, 231.
19. R. E. Rosenfield, R. Parthasarathy and J. D. Dunitz, J. Am. Chem. Soc., 1977, 99, 4860; G. R. Desiraju and R. Parthasarathy, J. Am. Chem. Soc., 1989, 111, 8725; N. Ramasubbu, R. Parthasarathy and P. Murray-Rust, J. Am. Chem. Soc., 1986, 108, 4308; E. Bosch and C. L. Barnes, Cryst. Growth Des., 2002, 2, 299.
20. R. E. Rosenfield, R. Parthasarathy and J. D. Dunitz, J. Am. Chem. Soc., 1977, 99, 4860; G. R. Desiraju and R. Parthasarathy, J. Am. Chem. Soc., 1989, 111, 8725; N. Ramasubbu, R. Parthasarathy and P. Murray-Rust, J. Am. Chem. Soc., 1986, 108, 4308; E. Bosch and C. L. Barnes, Cryst. Growth Des., 2002, 2, 299.
21. R. E. Rosenfield, R. Parthasarathy and J. D. Dunitz, J. Am. Chem. Soc., 1977, 99, 4860; G. R. Desiraju and R. Parthasarathy, J. Am. Chem. Soc., 1989, 111, 8725; N. Ramasubbu, R. Parthasarathy and P. Murray-Rust, J. Am. Chem. Soc., 1986, 108, 4308; E. Bosch and C. L. Barnes, Cryst. Growth Des., 2002, 2, 299.
22. R. E. Rosenfield, R. Parthasarathy and J. D. Dunitz, J. Am. Chem. Soc., 1977, 99, 4860; G. R. Desiraju and R. Parthasarathy, J. Am. Chem. Soc., 1989, 111, 8725; N. Ramasubbu, R. Parthasarathy and P. Murray-Rust, J. Am. Chem. Soc., 1986, 108, 4308; E. Bosch and C. L. Barnes, Cryst. Growth Des., 2002, 2, 299.
23. G. R Desiraju and T. Steiner, The Weak Hydrogen Bond In Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
24. R. K. R. Jetti, P. K. Thallapally, F. Xue, T. C. W. Mak and A. Nangia, Tetrahedron, 2000, 56, 6707; D. S. Reddy, D. C. Craig and G. R. Desiraju, J. Am. Chem. Soc., 1996, 118, 4090.
25. R. K. R. Jetti, P. K. Thallapally, F. Xue, T. C. W. Mak and A. Nangia, Tetrahedron, 2000, 56, 6707; D. S. Reddy, D. C. Craig and G. R. Desiraju, J. Am. Chem. Soc., 1996, 118, 4090.
26. O. Hassel, Science, 1970, 170, 497; A. V. Vasilyev, S. V. Lindeman and J. K. Kochi, Chem. Commun., 2001, 909.
27. O. Hassel, Science, 1970, 170, 497; A. V. Vasilyev, S. V. Lindeman and J. K. Kochi, Chem. Commun., 2001, 909.
28. R. Boese, T. Clark and A. Gavezzotti, Helv. Chim. Acta, 2003, 86, 1085; R. Boese and M. Kirchner, unpublished results.
29. R. Boese, T. Clark and A. Gavezzotti, Helv. Chim. Acta, 2003, 86, 1085; R. Boese and M. Kirchner, unpublished results.
30. S. Takahashi, Y. Kuroyama, K. Sonogashira and N. Hagihara, Synthesis, 1980, 627.
31. SHELXTL. Version 6.12, Bruker AXS Inc., Madison, WI, USA, 2000.
32. A. J. Deeming, G. Hogarth, M. Lee, M. Saha, S. P. Redmond, H. Phetmung and A. G. Orpen, Inorg. Chim. Acta, 2000, 309, 109.
33. T. Steiner, E. B. Starikov, A. M. Amado and J. J. C. Teixeria-Dias, J. Chem. Soc., Perkin Trans. 2, 1995, 1321.
34. D. Mootz and A. Deeg, J. Am. Chem. Soc., 1992, 114, 5888.
35. J. Trotter, S. H. Whitlow and T. Zobel, J. Chem. Soc. A, 1966, 353; V. R. Sarma, Indian J. Pure Appl. Phys., 1966, 4, 226; J. H. Palm, Acta Crystallogr., 1966, 21, 473; G. Plough-Sørensen and E. K. Anderson, Acta Crystallogr., Sect. C, 1985, 41, 613; H. Takazawa, S. Ohba and Y. Saito, Acta Crystallogr., Sect. B, 1989, 45, 432.
36. J. Trotter, S. H. Whitlow and T. Zobel, J. Chem. Soc. A, 1966, 353; V. R. Sarma, Indian J. Pure Appl. Phys., 1966, 4, 226; J. H. Palm, Acta Crystallogr., 1966, 21, 473; G. Plough-Sørensen and E. K. Anderson, Acta Crystallogr., Sect. C, 1985, 41, 613; H. Takazawa, S. Ohba and Y. Saito, Acta Crystallogr., Sect. B, 1989, 45, 432.
37. J. Trotter, S. H. Whitlow and T. Zobel, J. Chem. Soc. A, 1966, 353; V. R. Sarma, Indian J. Pure Appl. Phys., 1966, 4, 226; J. H. Palm, Acta Crystallogr., 1966, 21, 473; G. Plough-Sørensen and E. K. Anderson, Acta Crystallogr., Sect. C, 1985, 41, 613; H. Takazawa, S. Ohba and Y. Saito, Acta Crystallogr., Sect. B, 1989, 45, 432.
38. J. Trotter, S. H. Whitlow and T. Zobel, J. Chem. Soc. A, 1966, 353; V. R. Sarma, Indian J. Pure Appl. Phys., 1966, 4, 226; J. H. Palm, Acta Crystallogr., 1966, 21, 473; G. Plough-Sørensen and E. K. Anderson, Acta Crystallogr., Sect. C, 1985, 41, 613; H. Takazawa, S. Ohba and Y. Saito, Acta Crystallogr., Sect. B, 1989, 45, 432.
39. J. Trotter, S. H. Whitlow and T. Zobel, J. Chem. Soc. A, 1966, 353; V. R. Sarma, Indian J. Pure Appl. Phys., 1966, 4, 226; J. H. Palm, Acta Crystallogr., 1966, 21, 473; G. Plough-Sørensen and E. K. Anderson, Acta Crystallogr., Sect. C, 1985, 41, 613; H. Takazawa, S. Ohba and Y. Saito, Acta Crystallogr., Sect. B, 1989, 45, 432.
40. A. K. Srivastava, Z. Kristallogr., 1978, 148, 21.
41. G. R. Desiraju, CrystEngComm, 2002, 4, 499.
42. O. Ermer and A. Eling, J. Chem. Soc., Perkin Trans. 2, 1994, 925.