Benzimidazol-2-ylcarbinols and Benzimidazol-2-yl Ketones: Novel Bifunctional Chelating Ligands for Copper

Inorganic Chemistry

Volumn 35, Issue 1, 1996, Pages 3-4

  Gorun, Sergiu M ^a   Stibrany, Robert T ^a   Katritzky, Alan R ^b   Slawinski, Jaroslaw J ^b,c   Faid Allah, Hassan ^b,d   Brunner, Frédéric ^b,e  

^a EXXONMOBIL UPSTREAM RESEARCH COMPANY   (United States)

^b University of Florida   (United States)

^c MEDICAL UNIVERSITY OF GDANSK   (Poland)

^d Alexandria University Faculty Of Science   (Egypt)

^e CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002944034     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic950698v     Document Type: Article

References (38)

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11. 6
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16. Recent reviews: (a) Kalyanasundaram, K. Photochemistry of Polypyridine and Porphyrin Complexes; Academic Press: London, 1992; Chapter 9.
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18. 10 procedure; mp 58-60 °C (lit. 60-61 °C).
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21. 14 claims BBIK in 8% yield, but the only evidence reported, its melting point, is about 95 deg higher than the true 190-191 °C. The above papers do not report metal complexation properties of BBIK.
22. Sprecher, A. C.; Zuberbühler, A. D Angew. Chem., Int. Ed. Engl. 1977, 16, 189.
23. Regel, E.; Büchel, K-H. Liebigs Ann. Chem. 1977, 145.
24. Bis(1-methylbenzimidazol-2-yl)carbinol, 4, BBICOH, was prepared by lithiating 1-methylbenzimidazole, 1, followed by reaction with ethyl formate and quenching with ammonium chloride. Experimental details are given in the Supporting Information.
25. Tris(1-methylbenzimidazol-2-yl)carbinol, 5, TBICOH, was prepared by lithiating 1, followed by reaction with ethyl chloroformate and quenching with ammonium chloride. Experimental details are given in the Supporting Information.
26. 1 (unweighted, based on F) = 0.048 for 4914 independent reflections with I > 3σ(I).
27. (a) Byers, P. K.; Canty, A. J.; Engelhardt, L. M.; Patrick, J. M.; White, A. H. J. Chem. Soc., Dalton Trans. 1985, 981.
28. (b) Annibale, G.; Canovese, L.; Cattalini L.; Natile G.; Biagini-Cingi, M.; Manotti-Lanfredi, A-M.; Tirripicchio, A. J. Chem. Soc., Dalton Trans. 1981, 2280.
29. (c) Fischer, B. E.; Sigel, H. J. Inorg. Nucl. Chem. 1975, 37, 2127.
30. See also Arali et al. (Arali, V. H.; Revankar, V. K.; Mahale, V. B.; Kulkarni, P. J. Transition Met. Chem. 1994, 19, 57) for N9(benzimidazole), O(carbonyl) coordination to metals.
31. 20
32. (a) Gorun, S. M.; Greaney, M. A. 1990 ACS Meeting, Boston, MA
33. (b) Gorun, S. M.; Greaney, M. A. To be submitted for publication.
34. 1 (unweighted, based on F) = 0.058 for 2896 independent reflections with I > 3σ(I).
35. x chromophores for other benzimidazole-containing ligands: Diguet, C.; Bernardinelli, A.; Bocquet, B.; Quattropani, A.; Williams; A. F. J. Am. Chem. Soc. 1992, 114, 7440 and references therein.
36. See. also: (b) Hendriks, H. M. J.; Birker, P M. M. W. L; Van Rijn, J.; Verschoor, G. C.; Reedijk, J. J. Am. Chem. Soc. 1982, 104, 3607.
37. (c) Patch, M. G.; Choi, H-K.; Chapman, D. R.; Bau, R.; McKee, V.; Reed, C. A. Inorg. Chem. 1990, 29, 110.
38. 13C-NMR, δ (MeCN): 34.93; 112.76; 121.35; 125.67; 128.47; 137.52; 140.78; 145.82; 174.48. Variable temperature NMR experiments in various solvents are currently addressing the possibility of fast exchange. UV-vis (MeCN) (λ, nm (ε)): 623 (3740), 361 (47 350), 319 (29 270).