NMR spectroscopic observation of a metal-free acetylide anion

Chemistry - An Asian Journal

Volumn 1, Issue 4, 2006, Pages 581-585

  Tanaka, Yoshiyuki ^a   Arakawa, Makoto ^a   Yamaguchi, Yohei ^a   Hori, Chieko ^a   Ueno, Masahiro ^a   Tanaka, Takeyuki ^b   Imahori, Tatsushi ^a   Kondo, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b KOBE UNIVERSITY   (Japan)

Author keywords

Carbanions; Density functional calculations; Metal free acetylide anions; Phosphazenes; Reactive intermediates

Indexed keywords

ALKYNE; ANION; CARBON; CATION; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKYNES; ANIONS; CARBON; CATIONS; CHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS;

EID: 33750585797     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200600099     Document Type: Article

References (44)

1. a) M. B. Smith, J. March, Advanced Organic Chemistry, 5th ed., Wiley, New York, 2001;
2. b) L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed., University Science Books, Colorado, 1999.
3. T. F. Briggs, M. D. Winemiller, D. B. Collum, R. L. Parsons, Jr., A. H. Davulcu, G. D. Harris, J. M. Fortunak, P. N. Confalone, J. Am. Chem. Soc. 2004, 126, 5427-5435.
4. C. Lambert, P. von R. Schleyer, Angew. Chem. 1994, 106, 1187-1199;
5. Angew. Chem. Int. Ed. Engl. 1994, 33, 1129-1140.
6. a) G. A. Olah, G. K. S. Prakash, J. Sommer, Superacids, Wiley, New York, 1985;
7. b) J. C. Walton, Rev. Chem. Intermed. 1984, 5, 249-291;
8. c) Carbenes (Eds.: M. Jones, Jr., R. A. Moss), Wiley, New York, 1973-1975.
9. a) C. H. DePuy, V. M. Bierbaum, Acc. Chem. Res. 1981, 14, 146-153;
10. b) R. R. Squires, Acc. Chem. Res. 1992, 25, 461-467.
11. a) H.-J. Gais, J. Muller, J. Vollhardt, J. Am. Chem. Soc. 1991, 113, 4002-4003;
12. b) H.-J. Gais, G. Hellmann, H. J. Lindner, Angew. Chem. 1990, 102, 96;
13. Angew. Chem. Int. Ed. Engl. 1990, 29, 100-103;
14. c) M. T. Reetz, S. Hütte, R. Goddard, Eur. J. Org. Chem. 1999, 2475-2478;
15. d) J.-S. Fruchart, H. Gras-Masse, O. Melnyk, Tetrahedron Lett. 2001, 42, 9153-9155;
16. e) T. E. Hogen-Esch, J. Smid, J. Am. Chem. Soc. 1966, 88, 307-318;
17. f) U. Groß, D. Pfeifer, J. Fluorine Chem. 2002, 113, 17-26.
18. a) W. Kemp, NMR in Chemistry: A Multinuclear Introduction, Macmillan, London, 1986;
19. b) R. J. Abraham, J. Fisher, P. Loftus, Introduction to NMR Spectroscopy, Wiley, Chichester, 1988;
20. c) G. C. Levy, R. L. Lichter, Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy, John Wiley & Sons, New York, 1981.
21. a) Y. Tanaka, Y. Kasai, S. Mochizuki, A. Wakisaka, E. H. Morita, C. Kojima, A. Toyozawa, Y. Kondo, M. Taki, Y. Takagi, A. Inoue, K. Yamasaki, K. Taira, J. Am. Chem. Soc. 2004, 126, 744-752;
22. b) Y. Tanaka, C. Kojima, E. H. Morita, Y. Kasai, K. Yamasaki, A. Ono, M. Kainosho, K. Taira, J. Am. Chem. Soc. 2002, 124, 4595-4601;
23. c) Y. Tanaka, E. H. Morita, H. Hayashi, Y. Kasai, T. Tanaka, K. Taira, J. Am. Chem. Soc. 2000, 122, 11 303-11 310;
24. d) Y. Tanaka, C. Kojima, T. Yamazaki, T. S. Kodama, K. Yasuno, S. Miyashita, A. Mei Ono, A. Ono, M. Kainosho, Y. Kyogoku, Biochemistry 2000, 39, 7074-7080;
25. e) Y. Tanaka, K. Taira, Chem. Commun. 2005, 2069.
26. R. Schwesinger, H. Schlemper, C. Hasenfratz, J. Willaredt, T. Dambacher, T. Breuer, C. Ottaway, M. Fletschinger, J. Boele, H. Fritz, D. Putzas, H. W. Rotter, F. G. Bordwell, A. V. Satish, G.-Z. Ji, E. M. Peters, K. Peters, H. G. von Schnering, L. Walz, Liebigs Ann. 1996, 1055-1081.
27. a) T. Imahori, Y. Kondo, J. Am. Chem. Soc. 2003, 125, 8082;
28. b) T. Imahori, C. Hori, Y. Kondo, Adv. Synth. Catal. 2004, 346, 1090-1092.
29. I. Leito, T. Rodima, I. A. Koppel, R. Schwesinger, V. M. Vlasov, J. Org. Chem. 1997, 62, 8479-8483.
30. a) F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456-463;
31. b) H. J. Reich, "Bordwell pKa Table", to be found under http://www.chem.-wisc.edu/areas/reich/pkatable, 2001-2006;
32. c) Y. Fu, L. Liu, R.-Q. Li, R. Liu, Q.-X. Guo, J. Am. Chem. Soc. 2004, 126, 814-822.
33. a) A. Streitwieser, D. Z. , Wang, M. Stratakis, A. Facchetti, R. Gareyev, A. Abbotto, J. A. Krom, K. V. Kilway, Can J. Chem. 1998, 76, 765-769;
34. b) F. Maran, D. Celadon, M. G. Severin, E. Vianello, J. Am. Chem. Soc. 1991, 113, 9320-9329.
35. J. Cavanagh, W. J. Fairbrother, A. G. Palmer III, N. J. Skelton, Protein NMR Spectroscopy, Academic Press, San Diego, 1996.
36. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, 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, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh (USA), 2003.
37. a) F. London, J. Phys. Radium 1937, 8, 397-409;
38. b) R. McWeeny, Phys. Rev. 1962, 126, 1028-1034;
39. c) R. Ditchfield, Mol. Phys. 1974, 27, 789-807;
40. d) K. Woliński, A. J. Sadlej, Mol. Phys. 1980, 41, 1419-1430;
41. e) K. Woliński, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260.
42. A. C. de Dios, Prog. Nucl. Magn. Reson. Spectrosc. 1996, 29, 229-278.
43. a) Z. B. Maksic, R. Vianello, J. Phys. Chem. A 2002, 106, 419-430;
44. b) I. Novak, X. M. Wei, W. S. Chin, J. Phys. Chem. A 2001, 105, 1783-1788.