A combined experimental and theoretical study of metallic salts of thiapentadienyl, sulfinylpentadienyl and butadienesulfonyls

Journal of Organometallic Chemistry

Volumn 690, Issue 5, 2005, Pages 1379-1395

  Gamero Melo, Prócoro ^a,b   Villanueva García, Manuel ^c   Robles, Juvencio ^c   Contreras, Rosalinda ^a,b   Paz Sandoval, M Angeles ^a,b  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

^b Universidad de Guanajuato ^*  (Mexico)

^c UNIVERSITY OF GUANAJUATO   (Mexico)

Author keywords

Alkaline metals; Anions; Heterodienes; S,O Ligands; Thiapentadienyl

Indexed keywords

ACTIVATION ENERGY; BUTADIENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; SOLVENTS; SYNTHESIS (CHEMICAL);

DEPROTONATION; GEOMETRICAL PROPERTIES; METALLIC SALTS;

SALTS;

BASE; CATION; LITHIUM; METAL; POTASSIUM; SODIUM; SOLVENT;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PROTON TRANSPORT; SYNTHESIS; THEORETICAL STUDY;

EID: 14144249407     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.12.014     Document Type: Article

References (83)

1. P. Powell Adv. Organomet. Chem. 26 1986 125 and references therein
2. H. Yasuda, and A. Nakamura J. Organomet. Chem. 285 1985 15 and references therein
3. H. Yasuda, M. Yamauchi, Y. Ohnuma, and A. Nakamura Bull. Chem. Soc. Jpn. 54 1981 1481
4. L.M. Pratt, and A. Streitwieser J. Org. Chem. 65 2000 290
5. D. Seyferth, and J. Pornet J. Org. Chem. 45 1980 1721
6. D. Seyferth, J. Pornet, and R.M. Weinstein Organometallics 1 1982 1651
7. R.D. Ernst, J.W. Freeman, P.N. Swepston, and D.R. Wilson J. Organomet. Chem. 402 1991 17
8. L. Stahl, H. Ma, R.D. Ernst, I. Hyla-Kryspin, R. Gleiter, and M.L. Ziegler J. Organomet. Chem. 326 1987 257
9. D.R. Wilson, L. Stahl, and R.D. Ernst R.B. King J.J. Eisch Organometallic Syntheses vol. 3 1986 Academic Press New York 136
10. J.R. Bleeke, Y.-F. Xie, W.-J. Peng, and M. Chiang J. Am. Chem. Soc. 111 1989 4118
11. J.R. Bleeke Acc. Chem. Res. 24 1991 271
12. C.W. Shoppee, and G.N. Henderson J. Chem. Soc. Chem. Commun. 1974 561
13. R.B. Bates, R.H. Carnighan, and C.E. Staples J. Am. Chem. Soc. 85 1963 3031
14. W. Oppolzer, R.L. Snowden, and D.P. Simmons Helv. Chim. Acta 64 1981 2002
15. H. Yasuda, T. Nishi, K. Lee, and A. Nakamura Organometallics 2 1983 21
16. H. Yashuda, K. Tatsumi, and A. Nakamura New Aspects of Carbanion Chemistry. Structure of Pentadienyl Anions and Butenediyl Dianions and their Roles in Organic and Inorganic Synthesis 1987 Elsevier Science Publishing Co. Inc. New York p. 59
17. G.J. Heiszwolf, and H. Kloosterziel Recl. Trav. Chim. Pays-Bas 86 1967 807
18. J.R. Bleeke, T. Haile, P.R. New, and M.Y. Chiang Organometallics 12 1993 517
19. M.E. Navarro-Clemente, P. Juarez-Saavedra, M. Cervantes-Vasquez, M.A. Paz-Sandoval, A.M. Arif, and R.D. Ernst Organometallics 21 2002 592
20. J.R. Bleeke, E. Donnay, and N.P. Rath Organometallics 21 2002 4099
21. I.I. Rangel Salas, M.A. Paz-Sandoval, and H. Nöth Organometallics 21 2002 4696
22. R.B. Bates, L.M. Kroposki, and D.E. Potter J. Org. Chem. 37 1972 560
23. G. Wolf, and E.-U. Würtwein Chem. Ber. 24 1991 889
24. J.A. Gutiérrez, M.A. Paz-Sandoval, and J. Robles J. Organomet. Chem. 599 2000 147
25. J.R. Bleeke, S.T. Luaders, and K.D. Robinson Organometallics 13 1994 1592
26. J.A. Gutierrez, M.E. Navarro Clemente, M.A. Paz-Sandoval, A.M. Arif, and R.D. Ernst Organometallics 18 1999 1068
27. H. Kloosterziel, J.A. Van Drunen, and P. Galama J. Chem. Soc. Chem. Commun. 1969 885
28. J.R. Bleeke, P.V. Hinkle, and N.P. Rath Organometallics 20 2001 1939
29. J.R. Bleeke, M.F. Ortwerth, and M. Chiang Organometallics 11 1992 2740
30. J.R. Bleeke, M.F. Ortwerth, and A.M. Rohde Organometallics 14 1995 2813
31. J.R. Bleeke, P.V. Hinkle, and N.P. Rath J. Am. Chem. Soc. 121 1999 595
32. R.L. Crumbie, and D.D. Ridley Aust. J. Chem. 34 1981 1017
33. J.J. Burger, T.B.R.A. Chen, E.R. De Waard, and H.O. Huisman Tetrahedron 36 1980 723
34. T.S. Chou, H.-H. Tso, and L.-J. Chang J. Chem. Soc. Perkin Trans. I 1985 515
35. R.C. Krug, J.A. Rigney, and G.R. Tichelaar J. Org. Chem. 27 1962 1305
36. A.R. Katritzky, M. Piffl, H. Lang, and E. Anders Chem. Rev. 99 1999 665 and references therein
37. R.H. Everhardous Rec. Trav. Chim. Pays-Bas 95 1976 153
38. S. Pagano, A. Mutch, F. Lefebvre, and J.-M. Basset J. Mol. Catal. A: Chem. 133 1998 61
39. R.H. Grubs, and S. Chang Tetrahedron 54 1998 4413
40. S.K. Armstrong, and B.A. Christie Tetrahedron Lett. 37 1996 9373
41. Y.-S. Shon, and T.R. Lee Tetrahedron Lett. 38 1997 1283
42. J.M. McIntosh Can. J. Chem. 52 1974 1934
43. J.M. McIntosh, and R.S. Steevensz Can. J. Chem. 55 1977 2442
44. J.M. McIntosh, and R.A. Sieler Can. J. Chem. 56 1978 226
45. J.M. McIntosh, and L.Z. Pillon Can. J. Chem. 62 1984 2089
46. J.N. Gardener, S. Kaiser, S. Krubiner, and H. Lucas Can. J. Chem. 51 1973 1419
47. M.G. Pettett, and A.B. Holmes J. Chem. Soc. Perkin trans. I 1985 1161
48. S.F. Birch, and D.T. McAllan J. Chem. Soc. 1951 2556
49. R.C. Krug, and D.E. Boswel J. Heterocycl. Chem. 4 1967 309
50. R. Glaser, and A. Streitwieser J. Org. Chem. 56 1991 6612
51. A. Abbotto, A. Streitwieser, and P. Schleyer J. Am. Chem. Soc. 119 1997 11255
52. R.C. Fort, D.A. Hrovat, and W.T. Borden J. Org. Chem. 58 1993 211
53. L.M. Pratt, and A. Streitwieser J. Org. Chem. 65 2000 290
54. S. Kalinowsky, S. Berger, and H.-O. Braun Carbon-13 NMR Spectroscopy 1991 John Wiley & Sons p. 134
55. S. Kalinowsky, S. Berger, and H.-O. Braun Carbon-13 NMR Spectroscopy 1991 John Wiley & Sons p. 185
56. S. Kalinowsky, S. Berger, and H.-O. Braun Carbon-13 NMR Spectroscopy 1991 John Wiley & Sons p. 187
57. S. Kalinowsky, S. Berger, and H.-O. Braun Carbon-13 NMR Spectroscopy 1991 John Wiley & Sons p. 417
58. H. Günther NMR Spectroscopy second ed. 1994 J. Wiley & Sons p. 124
59. D.R. Wilson, R.D. Ernst, and T.H. Cymbaluk Organometallics 2 1983 1220
60. W. Trakarnpruk, A.M. Arif, and R.D. Ernst Organometallics 13 1994 2423
61. W. Trakarnpruk, A.M. Arif, and R.D. Ernst Organometallics 11 1992 1686
62. P. Gamero-Melo, M. Cervantes-Vásquez, A. Ramirez-Monroy, M.E. Sánchez-Castro, and M.A. Paz-Sandoval Organometallics 23 2004 3290
63. J.R. Torres Lubián, personal communication. The solid sample isolated at room temperature from reaction of 1Li was analyzed by GPC giving molecular weight of 19,496 (UV). Another signal of low molecular weight may suggest the presence of oligomers
64. G.A. Russell, and S.A. Weiner J. Org. Chem. 31 1966 248
65. E.J. Corey, and M. Chaykovsky J. Am. Chem. Soc. 87 1965 1345
66. P. Gamero-Melo, M.A. Paz-Sandoval, unpublished results
67. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, and R. Taylor J. Chem. Soc. Perkin Trans. II 1987 S1 S19
68. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, and R. Taylor J. Chem. Soc. Perkin Trans II 1989 S1 S83
69. I. Fleming Frontier Orbitals and Organic Chemical Reactions 1976 J. Wiley New York
70. A reviewer has suggest us that charge/radius ratio should be also consider as an important factor
71. R.G. Pearson Chemical Hardness: Applications from Molecules to Solids 1997 Wiley-VCH Verlag GMBH Weinheim
72. K.D. Sen D.M.P. Mingos Chemical Hardness: Structure and Bonding 1993 Springer-Verlag Berlin
73. R.G. Parr, and W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford University Press Oxford
74. R.G. Pearson Hard and Soft Acids and Bases 1973 Dowden, Hutchinson and Ross Stroudsberg, PA
75. R.G. Pearson J. Chem. Educ. 64 1987 561
76. R.G. Parr, and P.K. Chattaraj J. Am. Chem. Soc. 113 1991 1854
77. P.K. Chattaraj, G.H. Liu, and R.G. Parr Chem. Phys. Lett. 237 1995 171
78. P.K. Chattaraj Proc. Indian Natl. Sci. Acad. Part A 62 1996 1133
79. D.E. Goldberg Genetic Algorithms ins Search, Optimization and Machine Learning 1989 Addison Wesley Massachusetts
80. W.J. Hehre, L. Radom, P.V.R. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1986 Wiley New York
81. Spartan, version 5.1.1., Wavefunction Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA, USA, 1999
82. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, and J.A. Pople Gaussian 94, revision E.2 1995 Gaussian, Inc. Pittsburgh, PA
83. Gauss View 2.0, Gaussian, Inc. Carnegie Office Park, Bldg. 6, Pittsburgh, PA. 15106, USA, 1998