Tris(tetramethylethylenediamine-sodium)-9,9-bianthryl - The Salt of a π Hydrocarbon Radical Trianion with Three Na+-Cπ Contacts to One Molecular Half

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 502-504

  Bock, Hans ^a   Havlas, Zdenek ^b   Hess, Delia ^a   Näther, Christian ^a  

^a GOETHE UNIVERSITY   (Germany)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Arenes; Density functional calculations; Radical ions; Reductions; Tetraanions

Indexed keywords

EID: 0032473376     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980302)37:4<502::aid-anie502>3.3.co;2-x     Document Type: Article

References (23)

1. H. Bock, K. Ruppert, C. Näther, Z. Havlas, H.-F. Herrmann, C. Arad, I. Göbel, A. John, J. Meuret, S. Nick, A. Rauschenbach, W. Seitz, T. Vaupel, B. Solouki, Angew. Chem. 1992, 104, 595; Angew. Chem. Int. Ed. Engl. 1992, 31, 550.
2. H. Bock, K. Ruppert, C. Näther, Z. Havlas, H.-F. Herrmann, C. Arad, I. Göbel, A. John, J. Meuret, S. Nick, A. Rauschenbach, W. Seitz, T. Vaupel, B. Solouki, Angew. Chem. 1992, 104, 595; Angew. Chem. Int. Ed. Engl. 1992, 31, 550.
3. H. Bock, C. Näther, Z. Havlas, A. John, C. Arad, Angew. Chem. 1994, 106, 931; Angew. Chem. Int. Ed. Engl. 1994, 33, 875.
4. H. Bock, C. Näther, Z. Havlas, A. John, C. Arad, Angew. Chem. 1994, 106, 931; Angew. Chem. Int. Ed. Engl. 1994, 33, 875.
5. a) H. Bock, C. Arad, C. Näther, Z. Havlas, J. Chem. Soc. Chem. Commun. 1995, 2393.
6. b) H. Bock, C. Näther, K. Ruppert, Z. Havlas, J. Am. Chem. Soc. 1992, 114, 6907.
7. c) H. Bock, K. Gharagozloo-Hubmann, C. Näther, N. Nagel, Z. Havlas, Angew. Chem. 1996, 108, 720; Angew. Chem. Int. Ed. Engl. 1996, 35, 631.
8. c) H. Bock, K. Gharagozloo-Hubmann, C. Näther, N. Nagel, Z. Havlas, Angew. Chem. 1996, 108, 720; Angew. Chem. Int. Ed. Engl. 1996, 35, 631.
9. methyl)] using the riding model. The asymmetric unit contains two independent benzene molecules at general positions as well as arranged around a crystallographic inversion center. The carbon center of one TMEDA ligand, disordered in two positions, has been refined with a split model (Figure 1C). Further details of the crystal structure determination may be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, Germany, (fax: (+49)7247-808-666 (Frau S. Höhler-Schlimm); E-mail: crysdata§fiz-karlsruhe.de) on quoting the depository number CSD-380 145.
10. + counterions 0.364 (Na1), 0.50 (Na2) and 0.274 (Na3).
11. + counterions 0.364 (Na1), 0.50 (Na2) and 0.274 (Na3).
12. + counterions 0.364 (Na1), 0.50 (Na2) and 0.274 (Na3).
13. + counterions 0.364 (Na1), 0.50 (Na2) and 0.274 (Na3).
14. H. Bock, A. John, C. Näther, Z. Havlas, Z. Naturforsch. B 1994, 49, 1339.
15. a) K. Müllen, M. Baumgarten, K. Müller, A. Böhnen, Angew. Chem. 1992, 104, 482; Angew. Chem. Int. Ed. Engl. 1992, 31, 448;
16. a) K. Müllen, M. Baumgarten, K. Müller, A. Böhnen, Angew. Chem. 1992, 104, 482; Angew. Chem. Int. Ed. Engl. 1992, 31, 448;
17. b) J. Mortensen, J. Heinze, J. Electroanal. Chem. 1984, 175, 333 and M. Dietrich, J. Mortensen, J. Heinze, Angew. Chem. 1985, 97, 502; Angew. Chem. Int. Ed. Engl. 1985, 24, 508;
18. b) J. Mortensen, J. Heinze, J. Electroanal. Chem. 1984, 175, 333 and M. Dietrich, J. Mortensen, J. Heinze, Angew. Chem. 1985, 97, 502; Angew. Chem. Int. Ed. Engl. 1985, 24, 508;
19. b) J. Mortensen, J. Heinze, J. Electroanal. Chem. 1984, 175, 333 and M. Dietrich, J. Mortensen, J. Heinze, Angew. Chem. 1985, 97, 502; Angew. Chem. Int. Ed. Engl. 1985, 24, 508;
20. c) cf. also M. Hoshino, K. Kimura, M. Imamura, Chem. Phys. Lett. 1973, 20, 294;
21. d) W. Huber, K. Müllen, J. Chem. Soc. Chem. Comm. 1980, 698.
22. -1). The charges in the doubly complexed anthracene half are predicted to be -0.50 in contrast to -0.82 in the uncomplexed one. Dimers with additional contacts (Na3-C26a-Na1) have not been calculated.
23. H. Bock, Z. Havlas, D. Hess, C. Näther, unpublished; cf. D. Hess, Diplomarbeit, Universität Frankfurt, 1996.