Functionalized tellurols: Synthesis, spectroscopic characterization by photoelectron spectroscopy, and quantum chemical study

Inorganic Chemistry

Volumn 47, Issue 5, 2008, Pages 1502-1511

  Khater, Brahim ^a   Guillemin, Jean Claude ^a   Bajor, Gábor ^b   Veszprémi, Tamás ^b  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 41849122289     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic701791h     Document Type: Article

References (38)

1. Guillemin, J.-C.; Bouayad, A.; Vijaykumar, D. Chem. Commun. 2000, 1163-1164.
2. Riague, El H.; Guillemin, J.-C. Organometallics 2002, 21, 68-73.
3. Bajor, G.; Veszprémi, T.; Riague, El H.; Guillemin, J.-C. Chem. - Eur. J. 2004, 10, 3649-3656.
4. Guillemin, J.-C.; Bajor, G.; Riague, El H.; Khater, B.; Veszprémi, T. Organometallics 2007, 26, 2507-2518.
5. (a) Natta, G. Giorn. Chim. Ind. Appl. 1926, 8, 367-370 ;
6. Chem. Abstr. 1926, 20:26352.
7. (b) Baroni, A. Atti Accad. Naz. Lincei, Cl. Sci. Fis., Mat. Nat., Rend. 1938, 27, 238-242 ;
8. Chem. Abstr. 1939, 33:1079.
9. (c) Sink, C. W.; Harvey, A. B. J. Chem. Soc. D 1969, 1023-1024.
10. (d) Bochmann, M.; Coleman, A. P.; Webb, K. J.; Hursthouse, M. B.; Mazid, M. Angew. Chem., Int. Ed. 1991, 30, 973-975.
11. (a) Bonasia, P. J.; Christou, V.; Arnold, J. J. Am. Chem. Soc. 1993, 115, 6777-6781.
12. (b) Siemeling, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 67-68.
13. (c) Timberlake, J. M.; Green, J.; Christou, V.; Arnold, J. J. Chem. Soc., Dalton Trans. 1998, 4029-4033.
14. (d) Sadekov, I. D.; Zakharov, A. V. Russ. Chem. Rev. 1999, 68, 909-923, and references therein.
15. Guillemin, J.-C.; Riague, El H.; Gal, J.-F.; Maris, P.-C.; Mo, O.; Yanez, M. Chem. - Eur. J. 2005, 11, 2145-2153.
16. Chen, M. T.; George, J. W. J. Organomet. Chem. 1968, 12, 401-403.
17. The decomposition of diallylic diselenide into the corresponding diallylic monoselenide has been reported. Even with the diallylditelluride at hand, to isolate a pure sample of compound 3 would be particularly challenging: the kinetic stability dramatically decreases between thiols and selenols as well as between selenols and tellurols, and allylic selenols are very reactive compounds (ref 2).
18. Seyferth, D.; Cohen, H. M. J. Organomet. Chem. 1963, 1, 15-21.
19. Petitprez, D.; Demaison, J.; Wlodarczak, G.; Guillemin, J.-C.; Møllendal, H. J. Phys. Chem. A 2004, 108, 1403-1408.
20. (a) Cederbaum, L. S.; Domcke, W. Adv. Chem. Phys. 1977, 36, 205-344.
21. (b) von Niessen, W.; Schirmer, J.; Cederbaum, L. S. Comput. Phys. Rep. 1984, 1, 57-125.
22. (a) Zakrzewski, V. G.; von Niessen, W. J. Comput. Chem. 1993, 14, 13-18.
23. (b) Zakrzewski, V. G.; Ortiz, J. V. Int. J. Quantum Chem. 1995, 53, 583-590.
24. (c) Zakrzewski, V. G.; Ortiz, J. V. Int. J. Quantum Chem. 1994, 28, 23-27.
25. (a) The PES of propene, cyclopropane, methanol and methanethiol were taken from: Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S. Handbook of HeI Photoelectron Spectra of Fundamental Organic Molecules; Japan Scientific Societies Press: Tokyo; Halsted Press: New York, 1981.
26. (b) See ref 3.
27. (c) The PES of vinyl alcohol was taken from: Albrecht, B.; Allan, M.; Haselbach, E.; Neuhaus, L.; Carrupt, P. A. Helv. Chim. Acta 1984, 67, 216-219.
28. (d) The PES of ethenethiol was taken from: Chin, W. S.; Mok, C. Y.; Huang, H. H. J. Electron Spectrosc. Relat. Phenom. 1994, 67, 173-179.
29. (e) The PESs of allyl mercaptan and allyl alcohol were taken from: Katrib, A.; Rabalais, J. W. J. Phys. Chem. 1973, 77, 2358-2363.
30. (f) The first four IPs of cyclopropanethiol are: 9.27, 10.91, 11.49, and 12.5 eV: Bajor, G.; Veszprémi, T. Unpublished results..
31. (a) Kimura, S.; Ito, S.; Yoshifuji, M.; Veszprémi, T. J. Org. Chem. 2003, 68, 6820-6823.
32. (b) de Meijere, A. Methoden der Organischen Chemie (Houben Weyl); Thieme: Stuttgart, Germany, 1996; Vol. E17 Carbocyclic Three- and Four-Membered Ring Compounds.
33. (c) de Meijere, A. Angew. Chem., Int. Ed. 1979, 18, 809-826.
34. Dabdoub, M. J.; Comasseto, J. V. J. Organomet. Chem. 1988, 344, 167-173.
35. Veszprémi, T.; Zsombok, Gy. Magy. Kern. Foly. 1986, 92, 39-40.
36. Frisch, M. J.; Tracks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, ; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
37. Molden: a pre- and post-processing program for molecular and electronic structures: Schaftenaar, G.; Noordik, J. H. J. Comput.-Aided Mol. Des. 2000, 14, 123-134.
38. Tucci, F. C.; Chieffi, A.; Comasseto, J. V.; Marino, J. P. J. Org. Chem. 1996, 61, 4975-4989.