Strength vs. Accessibility: Unraveling the patterns of self-recognition in a conformationally locked amino alcohol

European Journal of Organic Chemistry

Volumn , Issue 5, 2008, Pages 805-815

  Mehta, Goverdhan ^a   Sen, Saikat ^a   Guru Row, Tayur N ^a   Chopra, Deepak ^a   Chattopadhyay, Sayani ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Amino alcohol; Experimental charge density; Hydrogen bonding; Self assembly

Indexed keywords

EID: 53649109659     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700778     Document Type: Article

References (52)

1. J. D. Dunitz, Pure Appl. Chem. 1991, 63, 177-185.
2. J. M. Robertson, in Organic Crystals and Molecules, Cornell University Press, Ithaca, New York, 1953.
3. M. C. Etter, Acc. Chem. Res. 1990, 23, 120-126.
4. a) J. D. Dunitz, W. B. Schweizer, CrystEngComm 2007, 9, 266-269;
5. b) D. S. Coombes, G. K. Nagi, S. L. Price, Chem. Phys. Lett. 1997, 265, 532-537.
6. H⋯⋯X < sum of van der Waals radii). Hence, in the absence of any substantiating evidence, it was not possible to term the amino protons in these crystal structures as true bystanders.
7. a) G. Mehta, S. Sen, S. S. Ramesh, Eur. J. Org. Chem. 2007, 423-436;
8. b) G. Mehta, S. Sen, CrystEngComm 2005, 7, 656-663;
9. c) G. Mehta, S. Sen, S. S. Ramesh, CrystEngComm 2005, 7, 563-568;
10. d) G. Mehta, S. Sen, K. Venkatesan, CrystEngComm 2005, 7, 398-401.
11. O. Ermer, A. Eling, J. Chem. Soc. Perkin Trans. 2 1994, 925-944.
12. S. Hanessian, R. Saladino, in Crystal Design. Structure and Function (Ed.: G. R. Desiraju), Perspectives in Supramolecular Chemistry, Wiley, New York, 2003, vol. 7, pp. 77-151.
13. A. Dey, M. T. Kirchner, V. R. Vangala, G. R. Desiraju, R. Mondal, J. A. K. Howard, J. Am. Chem. Soc. 2005, 127, 10545-10559 and references cited therein.
14. a) C. F. Matta, in Hydrogen Bonding - New Insights (Ed.: S. J. Grabowski), Springer, 2006, pp. 337-376;
15. b) D. J. Wolstenholme, T. S. Cameron, J. Phys. Chem. B 2006, 110, 8970-8978.
16. For recent references on experimental charge density studies in organic molecules, see: a) S. Grabowsky, T. Pfeuffer, L. Chȩcińska, M. Weber, W. Morgenroth, P. Luger, T. Schirmeiter, Eur. J. Org. Chem. 2007, 2759-2768;
17. b) B. Dittrich, T. Koritsanszky, A. Volkov, S. Mebs, P. Luger, Angew. Chem. Int. Ed. 2007, 46, 2935-2938;
18. Angew. Chem. 2007, 119, 2993-2996;
19. c) L. Chȩcińska, S. I. Troyanov, S. Mebs, C. B. Hübschle, P. Luger, Chem. Commun. 2007, 4003-4005;
20. d) E. A. Zhurova, A. I. Stash, V. G. Tsirelson, V. V. Zhurov, E. V. Bartashevich, V. A. Potemkin, A. A. Pinkerton, J. Am. Chem. Soc. 2006, 128, 14728-14734;
21. e) L. Chȩcińska, S. Mebs, C. B. Huebschle, D. Foerster, W. Morgenroth, P. Luger, Org. Biomol. Chem. 2006, 4, 3242-3251;
22. f) D. Chopra, T. S. Cameron, J. D. Ferrara, T. N. Guru Row, J. Phys. Chem. A 2006, 110, 10465-10477;
23. g) R. Destro, R. Soave, M. Barzaghi, L. Lo Presti, Chem. Eur. J. 2005, 11, 4621-4634;
24. h) P. Coppens, Angew. Chem. Int. Ed. 2005, 44, 6810-6811;
25. Angew. Chem. 2005, 117, 6970-6972;
26. i) M. Messerschmidt, S. Scheins, L. Grubert, M. Pätzel, G. Szeimies, C. Paulmann, P. Luger, Angew. Chem. Int. Ed. 2005, 44, 3925-3928;
27. Angew. Chem. 2005, 117, 3993-3997.
28. T. Koritsanszky, T. Richter, P. Macci, C. Gatti, S. Howard, P. R. Mallinson, L. Farrugia, Z. W. Su, N. K. Hansen, XD, A Computer Program Package for Multipole Refinement and Analysis of Electron Densities from Diffraction Data, Tech. Rep., Freie University of Berlin, Berlin, Germany, 2003.
29. N. K. Hansen, P. Coppens, Acta Crystallogr., Sect. A 1978, 34, 909-921.
30. F. L. Hirshfeld, Acta Crystallogr., Sect. A 1976, 32, 239-244.
31. a) R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford, UK, 1990;
32. b) R. F. W. Bader, J. Phys. Chem. A 1998, 102, 7314-7323.
33. U. Koch, P. L. A. Popelier, J. Phys. Chem. 1995, 99, 9747-9754.
34. See electronic supporting information for details.
35. Y. A. Abramov, Acta Crystallogr., Sect. A 1997, 53, 264-272.
36. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 1998, 285, 170-173.
37. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.11.3, Gaussian, Inc., Pittsburgh PA, 2002.
38. -1.
39. Bruker. SMART (Version 6.028), SAINT (Version 6.02), XPREP. Bruker AXS Inc., Madison, Wisconsin, USA, 1998.
40. G. M. Sheldrick, SADABS, University of Göttingen, Germany, 1996.
41. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
42. G. M. Sheldrick, SHELXS97 and SHELXL97, University of Göttingen, Germany, 1997.
43. M. Nardelli, J. Appl. Crystallogr. 1995, 28, 659.
44. A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.
45. P. Munshi, T. N. Guru Row, Acta Crystallogr., Sect. B 2002, 58, 1011-1017.
46. a) R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426;
47. b) R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-38.
48. L. J. Farrugia, J. Appl. Crystallogr. 1993, 32, 837-838.
49. D. M. Watkin, L. Pearce, C. K. Prout, CAMERON - A Molecular Graphics Package, Chemical Crystallography Laboratory, University of Oxford, 1993
50. E. Clementi, C. Roetti, Atomic Data and Nuclear Data Tables, 1974, 14, 177-478.
51. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
52. F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 380-388.