Stereochemistry of 2,6-diaminoadamantane salts: Transannular interactions

European Journal of Organic Chemistry

Volumn , Issue 19, 2011, Pages 3500-3506

  Glaser, Robert ^a   Steinberg, Avital ^a   Šekutor, Marina ^b   Rominger, Frank ^c   Trapp, Oliver ^c   Mlinarić Majerski, Kata ^b  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b RUDER BO KOVI INSTITUTE   (Croatia)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Adamantane; Pseudo symmetry quantification; Structure elucidation; Substituent effects

Indexed keywords

EID: 79959706708     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001635     Document Type: Article

References (35)

1. E. J. Gabbay, Biopolymers 1967, 5, 727-747.
2. E. J. Gabbay, R. R. Shimshak, Biopolymers 1968, 6, 255-268.
3. I. Ergaz, R. A. Toscano, G. Delgado, A. Steinberg, R. Glaser, Cryst. Growth Des. 2008, 8, 1399-1405.
4. O. Böttger, Ber. Dtsch. Chem. Ges. 1937, 70, 314-325.
5. H. Stetter, O. Bänder, Chem. Ber. 1955, 88, 1535-1537.
6. H. Gerlach, Chimia 1972, 26, 660-661.
7. H. Gerlach, Helv. Chim. Acta 1972, 55, 2773-2776.
8. M. Nakazaki, H. Chikamatsu, M. Nishino, H. Murakami, J. Org. Chem. 1981, 46, 1151-1156.
9. R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-447;
10. Angew. Chem. Int. Ed. Engl. 1966, 5, 385 -415.
11. V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614-631;
12. Angew. Chem. Int. Ed. Engl. 1982, 21, 567 -583.
13. H. Gerlach, Helv. Chim. Acta 1985, 68, 1815-1821.
14. F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 380-388.
15. G. R. Desiraju, CrystEngComm 2007, 9, 91-92.
16. A. Gavezzotti, CrystEngComm 2008, 10, 389-398.
17. H. Zabrodsky, S. Peleg, D. Avnir, J. Am. Chem. Soc. 1992, 114, 7843-7851.
18. H. Zabrodsky, S. Peleg, D. Avnir, J. Am. Chem. Soc. 1993, 115, 8278-8289.
19. M. Pinsky, D. Avnir, Inorg. Chem. 1998, 37, 5575-5582.
20. M. Pinsky, D. Casanova, P. Alemany, S. Alvarez, D. Avnir, C. Dryzun, Z. Kizner, A. Sterkin, J. Comput. Chem. 2008, 29, 190-197.
21. A. Steinberg, I. Ergaz, R. A. Toscano, R. Glaser, Cryst. Growth Design 2011, 11, 1262-1270.
22. H. W. Geluk, J. L. M. A. Schlatmann, Recueil Trav. Pays-Bas 1971, 90, 516-520.
23. T. G. Archibald, K. J. Baum, Org. Chem. 1988, 53, 4645-4649.
24. J. A. Secrist III, M. W. Logue, J. Org. Chem. 1972, 37, 335-336.
25. R. E. Bowman, H. H. Stroud, J. Chem. Soc. 1950, 1342-1345.
26. S. Liu, C. Ruspic, P. Mukhopadhyay, S. Chakrabarti, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2005, 127, 15959-15967.
27. J. Echeverría, A. Carreras, D. Casanova, P. Alemany, S. Alvarez, Chem. Eur. J. 2011, 17, 359-367.
28. J. Bernstein, R. E. Davis, I. Shimoni, N.-L. Chang, Angew. Chem. Int. Ed. Engl. 1995, 34, 1555-1573.
29. E. Shefter, E. E. Smissman, J. Pharm. Sci. 1971, 60, 1364-1367.
30. B. Lee, G. M. Henry, Acta Crystallogr., Sect. B: Struct. Sci. 1976, 32, 938-940.
31. M. A. James, J. A. C. Clyburne, A. Linden, B. D. James, J. Liesegang, V. Zuzich, Can. J. Chem. 1996, 74, 1490-1502.
32. SAINT, v. 2007, Bruker, Madison, WI, 2007.
33. G. M. Sheldrick, SADABS, v. 2008/1, Bruker, Madison, WI, 2008.
34. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112-122.
35. M. Pinsky, D. Yogev-Einot, D. Avnir, J. Comput. Chem. 2003, 24, 786-796.