Synthesis, characterization and Schlenk equilibrium studies of methylmagnesium compounds with O- and N-donor ligands - The unexpected behavior of [MgMeBr(pmdta)] (pmdta = N,N,N′,N″,N″- pentamethyldiethylenetriamine)

Journal of Organometallic Chemistry

Volumn 690, Issue 5, 2005, Pages 1178-1191

  Yousef, Rushdi I ^a   Walfort, Bernhard ^b   Rüffer, Tobias ^b   Wagner, Christoph ^a   Schmidt, Harry ^a   Herzog, Renate ^a   Steinborn, Dirk ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

DFT calculations; Dimethylmagnesium; Grignard compounds; Methylmagnesium bromide; Pmdta (N,N,N ,N ,N pentamethyldiethylenetriamine); Schlenk equilibrium

Indexed keywords

ALCOHOLS; ETHERS; MOISTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS; SYNTHESIS (CHEMICAL);

EQUILIBRIUM CONSTANTS; GRIGNARD COMPOUNDS; NEEDLE-LIKE CRYSTALS; TETRAHYDROFURAN (THF);

ORGANOMETALLICS;

CARBON 13; DIETHYLENETRIAMINE; HYDROGEN; LIGAND; MAGNESIUM DERIVATIVE; METHYL GROUP; MONOMER; N,N,N',N'',N'' PENTAMETHYLDIETHYLENETRIAMINE; NITROGEN; ORGANOMETALLIC COMPOUND; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; CRYSTAL STRUCTURE; EQUILIBRIUM CONSTANT; GRIGNARD REACTION; HIGH TEMPERATURE; METALLURGY; MICROANALYSIS; MOISTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; QUANTUM YIELD; REACTION ANALYSIS; ROOM TEMPERATURE; SENSITIVITY ANALYSIS; SOLVENT EFFECT; STRUCTURE ANALYSIS; SURFACE PROPERTY; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

EID: 14144256453     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.10.058     Document Type: Article

References (39)

1. A. Inoue, and K. Oshima H. Yamamoto K. Oshima Main Group Metals in Organic Synthesis 2004 Wiley-VCH Weinheim 51 154
2. H.G. Richey Jr. Grignard Reagents: New Developments 2000 Wiley Chichester
3. B.J. Wakefield Organomagnesium Methods in Organic Synthesis 1995 Academic Press London
4. K.C. Cannon, and G.R. Krow G.S. Silverman P.E. Rakita Handbook of Grignard Reagents 1996 Marcel Dekker New York 271 289
5. W. Schlenk, and W. Schlenk Jr. Chem. Ber. 62 1929 920 924
6. W.E. Lindsell G. Wilkinson F.G.A. Stone E.W. Abel Comprehensive Organometallic Chemistry vol. 1 1982 Pregamon Press Oxford 155 252
7. W.E. Lindsell E.W. Abel F.G.A. Stone G. Wilkinson Comprehensive Organometallic Chemistry II vol. 1 1995 Pregamon Press/Elsevier Oxford 57 127
8. J. Axten, J. Troy, P. Jiang, M. Trachtman, and C.W. Bock Struct. Chem. 5 1994 99 108
9. A.W. Ehlers, G.P.M. van Klink, M.J. van Eis, F. Bickelhaupt, P.H.J. Niederkoorn, and K. Lammertsma J. Mol. Model. 6 2000 186 194
10. J. Tammiku, P. Burk, and A. Tuulmets J. Phys. Chem. A 105 2001 8554 8561
11. J. Tammiku-Taul, P. Burk, and A. Tuulmets J. Phys. Chem. A 108 2004 133 139
12. W. Schlenk Jr. Chem. Ber. 64 1931 736 739
13. F. Bickelhaupt H.G. Richey Jr. Grignard Reagents: New Developments 2000 Wiley Chichester 299 328
14. H.L. Uhm G.S. Silverman P.E. Rakita Handbook of Grignard Reagents 1996 Marcel Dekker New York 117 144
15. P.R. Markies, O.S. Akkerman, F. Bickelhaupt, W.J.J. Smeets, and A.L. Spek Adv. Organomet. Chem. 32 1991 147 226
16. M. Vallino J. Organomet. Chem. 20 1969 1 10
17. S. Sakamoto, T. Imamoto, and K. Yamaguchi Org. Lett. 3 2001 1793 1795
18. M. Veith, A. Spaniol, J. Pöhlmann, F. Gross, and V. Huch Chem. Ber. 126 1993 2625 2635
19. H. Viebrock, and E. Weiss J. Organomet. Chem. 464 1994 121 126
20. A.M. Bradford, D.C. Bradley, M.B. Hursthouse, and M. Motevalli Organometallics 11 1992 111 115
21. J.E. Huheey, E.A. Keiter, and R.L. Keiter Inorganic Chemistry, Principles of Structure and Reactivity fourth ed. 1993 Harper-Collins New York
22. V. Gutmann The Donor-Acceptor Approach to Molecular Interactions 1978 Plenum Press New York pp. 1-16
23. G. Fraenkel, D.G. Adams, and J. Williams Tetrahedron Lett. 1963 767 773
24. H.A. Bent Chem. Rev. 61 1961 275 311
25. S. Schade, and G. Boche J. Organomet. Chem. 550 1998 359 379
26. F.W. Walker, and E.C. Ashby J. Am. Chem. Soc. 91 1969 3845 3850
27. G.E. Parris, and E.C. Ashby J. Am. Chem. Soc. 93 1971 1206 1213
28. E.C. Ashby, G. Parris, and F. Walker Chem. Commun. 1969 1464
29. T.D.W. Claridge High-Resolution NMR Techniques in Organic Chemistry 1999 Pergamon Press Amsterdam
30. S. Miertus, and J. Tomasi Chem. Phys. 65 1982 239 245
31. V. Barone, M. Cossi, and J. Tomasi J. Comput. Chem. 19 1998 404 417 and references cited therein
32. F. Ehrenberger Quantitative Organische Elementaranalyse 1991 VCH Weinheim pp. 555-556
33. Data obtained by PERCH Computer Software, University of Kuopio, Finland, 2000
34. G.M. Sheldrick shelxs-97, shelxl-97: Programs for Crystal Structure Determination 1990-1997 University of Göttingen Göttingen, Germany
35. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople gaussian-98, Revision A.3 1998 Gaussian, Inc. Pittsburgh, PA
36. A.D. Becke Phys. Rev. A 38 1988 3098 3100
37. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
38. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
39. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch J. Phys. Chem. 98 1994 11623 11627