Aggregation of donor base stabilized 2-thienyllithium in a single crystal and in solution: Distances from X-ray diffraction and the nuclear overhauser effect

Journal of the American Chemical Society

Volumn 134, Issue 2, 2012, Pages 1344-1351

  Granitzka, Markus ^a   Pöppler, Ann Christin ^a   Schwarze, Eike K ^a   Stern, Daniel ^a   Schulz, Thomas ^a   John, Michael ^a   Herbst Irmer, Regine ^a   Pandey, Sushil K ^b   Stalke, Dietmar ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF JAMMU   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2-THIENYLLITHIUM; EXCHANGE SPECTROSCOPIES; HETERONUCLEAR; HYDROGEN ATOMS; LINEAR REGION; LITHIATION; NITROGEN DONORS; NUCLEAR OVERHAUSER EFFECTS; PARTIAL DISSOCIATION; TOLUENE MOLECULES; TOLUENE SOLUTION;

CRYSTAL STRUCTURE; DEUTERIUM; HYDROGEN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; SPIN-LATTICE RELAXATION; THIOPHENE; TOLUENE; X RAY DIFFRACTION;

X RAY DIFFRACTION ANALYSIS;

DEUTERIUM; HYDROGEN; LITHIUM DERIVATIVE; NITROGEN; THIOPHENE; TOLUENE;

ARTICLE; AUXILIARY EXCHANGE SPECTROSCOPY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DISSOCIATION; LITHIATION; MOLECULAR DYNAMICS; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SPECTROSCOPY; SYNTHESIS; X RAY DIFFRACTION;

EID: 84855923567     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja210382c     Document Type: Article

References (83)

1. Biehl, E. R. Prog. Heterocycl. Chem. 2011, 22, 109-141
2. Chinchilla, R.; Nájera, C.; Yus, M. ARKIVOC 2007, 10, 152-231
3. Blair, V. L.; Kennedy, A. R.; Mulvey, R. E.; O'Hara, C. T. Chem.-Eur. J. 2010, 16, 8600-8604
4. Belo, D.; Almeida, M. Coord. Chem. Rev. 2010, 254, 1479-1492
5. Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics [Online]; John Wiley & Sons: Chichester, U.K., 2009. http://www.amazon.com/Handbook-Thiophene-Based-Materials-Applications- Electronics/dp/0470057327, accessed 7/27/11.
6. For a review see, e.g.: Liu, Y.; Liu, Y.; Zhan, X. Macromol. Chem. Phys. 2011, 212, 428-443
7. Petti, F.; Thelemann, A.; Kahler, J.; McCormack, S.; Castaldo, L.; Hunt, T.; Nuwaysir, L.; Zeiske, L.; Haack, H.; Sullivan, L.; Garton, A.; Haley, J. D. Mol. Cancer Ther. 2005, 4, 1186-1197
8. Sweeney, N. J.; Gallagher, W. M.; Müller-Bunz, H.; Pampillón, C.; Strohfeldt, K.; Tacke, M. J. Inorg. Biochem. 2006, 100, 1479-1486
9. Selinka, C.; Stalke, D. Eur. J. Inorg. Chem. 2003, 3376-3382
10. Selinka, C.; Stalke, D. Z. Naturforsch. 2003, 58b, 291-298
11. Collum, D. B. Acc. Chem. Res. 1992, 25, 448-454
12. DePue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5518-5524
13. DePue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524-5533
14. Galiano-Roth, A. S.; Collum, D. B. J. Am. Chem. Soc. 1989, 111, 6772-6778
15. Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 4081-4086
16. Jantzi, K. L.; Puckett, C. L.; Guzei, I. A.; Reich, H. J. J. Org. Chem. 2005, 70, 7520-7529
17. Reich, H. J.; Whipple, W. L. Can. J. Chem. 2005, 83, 1577-1587
18. Reich, H. J.; Green, D. P.; Medina, M. A.; Goldenberg, W. S.; Gudmundsson, B. O.; Dykstra, R. R.; Phillips, N. H. J. Am. Chem. Soc. 1998, 120, 7201-7210
19. Shen, K.; Fu, Y.; Li, J.-N.; Liu, L.; Guo, Q.-X. Tetrahedron 2007, 63, 1568-1576
20. Spek, A. L.; Veldman, N. Private communication to the Cambridge Crystallographic Data Centre, 1999; RefCode HIGPOC.
21. Powell, D. R.; Whipple, W. L.; Reich, H. J. Acta Crystallogr., Sect. C 1996, 52, 1346-1348
22. Spek, A. L.; Lakin, M. T.; den Besten, R. Private communication to the Cambridge Crystallographic Data Centre, 1999; RefCode LEDSES.
23. Spek, A. L.; Smeets, W. J. J. Private communication to the Cambridge Crystallographic Data Centre, 1999; RefCode JUJXER.
24. Spek, A. L. Private communication to the Cambridge Crystallographic Data Centre, 1999; RefCode HIGXUQ.
25. Harder, S.; Boersma, J.; Brandsma, L.; Kanters, J. A.; Bauer, W.; Pi, R.; Schleyer, P. v. R.; Schöllhorn, H.; Thewalt, U. Organometallics 1989, 8, 1688-1696
26. Dinnebier, R. E.; Behrens, U.; Olbrich, F. J. Am. Chem. Soc. 1998, 120, 1430-1433
27. Hope, H.; Power, P. P. J. Am. Chem. Soc. 1983, 105, 5320-5324
28. Thoennes, D.; Weiss, E. Chem. Ber. 1978, 111, 3157-3161
29. Schümann, U.; Kopf, J.; Weiss, E. Angew. Chem. 1985, 97, 222-223
30. Angew. Chem., Int. Ed. Engl. 1985, 24, 215-216.
31. Weiss, E.; Lambertsen, T.; Schubert, B.; Cockcroft, J. K.; Wiedenmann, A. Chem. Ber. 1990, 123, 79-81
32. Ogle, C. A.; Huckabee, B. K.; Johnson, H. C., IV; Sims, P. F.; Winslow, S. D.; Pinkerton, A. A. Organometallics 1993, 12, 1960-1963
33. Köster, H.; Thoennes, D.; Weiss, E. J. Organomet. Chem. 1978, 160, 1-5
34. Walfort, B.; Lameyer, L.; Weiss, W.; Herbst-Irmer, R.; Bertermann, R.; Rocha, J.; Stalke, D. Chem.-Eur. J. 2001, 7, 1417-1423
35. Kottke, T.; Stalke, D. J. Appl. Crystallogr. 1993, 26, 615-619
36. Kottke, T.; Lagow, R. J.; Stalke, D. J. Appl. Crystallogr. 1996, 29, 465-468
37. Stalke, D. Chem. Soc. Rev. 1998, 27, 171-178
38. Gessner, V. H.; Däschlein, C.; Strohmann, C. Chem.-Eur. J. 2009, 15, 3320-3334
39. Stey, T.; Stalke, D. Lead structures in lithium organic chemistry. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Marek, I., Eds.; John Wiley & Sons: Chichester, U.K., 2004; pp 47-120
40. Stalke, D. Angew. Chem. 1994, 106, 2256-2259
41. Angew. Chem., Int. Ed. Engl. 1994, 33, 2168-2171.
42. Weiss, E. Angew. Chem. 1993, 105, 1565-1587
43. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501-1523.
44. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353-451
45. Schleyer, P. v. R. Pure Appl. Chem. 1983, 55, 355-362
46. Stalke, D. Chem.-Eur. J. 2011, 17, 9264-9278
47. Deuerlein, S.; Leusser, D.; Flierler, U.; Ott, H.; Stalke, D. Organometallics 2008, 27, 2306-2315
48. Bickelhaupt, F. M.; Solà, M.; Guerra, C. F. J. Chem. Theory Comput. 2006, 2, 965-980
49. Matito, E.; Poater, J.; Bickelhaupt, F. M.; Solà, M. J. Phys. Chem. B 2006, 110, 7189-7198
50. CRC Handbook of Chemistry and Physics, 87 th ed.; Lide, D. R., Ed.; Chemical Rubber Publishing Co.: Boca Raton, FL, 2006.
51. Stern, D.; Finkelmeier, N.; Meindl, K.; Henn, J.; Stalke, D. Angew. Chem. 2010, 122, 7021-7024
52. Angew. Chem., Int. Ed. 2010, 49, 6869-6872.
53. Stalke, D.; Whitmire, K. H. Chem. Commun. 1990, 833-834
54. Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47-142
55. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167-209
56. Schiemenz, B.; Power, P. P. Angew. Chem. 1996, 108, 2288-2290
57. Angew. Chem., Int. Ed. Engl. 1996, 35, 2150-2151.
58. Kottke, T.; Stalke, D. Angew. Chem. 1993, 105, 619-621
59. Angew. Chem., Int. Ed. Engl. 1993, 32, 580-582.
60. Strohmann, C.; Seibel, T.; Strohfeldt, K. Angew. Chem. 2003, 115, 4669-4671
61. Angew. Chem., Int. Ed. 2003, 42, 4531-4533.
62. Edelmann, F. T.; Knösel, F.; Pauer, F.; Stalke, D.; Bauer, W. J. Organomet. Chem. 1992, 438, 1-10
63. Hoffmann, D; Bauer, W.; Schleyer, P. v. R.; Pieper, U.; Stalke, D. Organometallics 1993, 12, 1193-1200
64. Kühnen, M.; Günther, H.; Amoureux, J.-P.; Fernandéz, C. Magn. Reson. Chem. 2002, 40, 24-30
65. Seebach, D.; Hässig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308-337
66. Fraenkel, G.; Chow, A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 6190-6198
67. Li, W.; Kagan, G.; Hopson, R.; Williard, P. G. ARKIVOC 2011, 5, 180-187
68. Valentini, M.; Pregosin, P. S.; Rüegger, H. Organometallics 2000, 19, 2551-2555
69. Keresztes, I.; Williard, P. G. J. Am. Chem. Soc. 2000, 122, 10228-10229
70. Li, D.; Sun, C.; Liu, J.; Hopson, R.; Li, W.; Williard, P. G. J. Org. Chem. 2008, 73, 2373-2381
71. Hassinen, A.; Moreels, I.; Donegá, C. d. M.; Martins, J. C.; Hens, Z. J. Phys. Chem. Lett. 2010, 1, 2577-2581
72. Heinzer, J.; Oth, J. F. M.; Seebach, D. Helv. Chim. Acta 1985, 68, 1848-1862
73. March's Advanced Organic Chemistry, 6 th ed.; Smith, M. B.; March, J., Eds.; Wiley-Interscience: Hoboken, NJ, 2007.
74. Neuhaus, D.; Williamson, M. P. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH: New York, 1989.
75. Gronenborn, A. M.; Clore, G. M. Prog. Nucl. Magn. Reson. Spectrosc. 1985, 17, 1-36
76. De Vries, T. S.; Goswami, A.; Liou, L. R.; Gruver, J. M.; Jayne, E.; Collum, D. B. J. Am. Chem. Soc. 2009, 131, 13142-13154
77. Schulz, T.; Meindl, K.; Leusser, D.; Stern, D.; Graf, J.; Michaelsen, C.; Ruf, M.; Sheldrick, G. M.; Stalke, D. J. Appl. Crystallogr. 2009, 42, 885-891
78. SAINT, version 7.68A; Bruker APEX, version 2011.9; Bruker AXS: Madison, WI, 2008.
79. Sheldrick, G. M. SADABS, 2008/2; Universität Göttingen, Göttingen, Germany, 2008.
80. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467-473
81. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122
82. Müller, P.; Herbst-Irmer, R.; Spek, A. L.; Schneider, T. R.; Sawaya, M. R. In Crystal Structure Refinement-A Crystallographer's Guide to SHELXL, IUCr Texts on Crystallography; Müller, P., Ed.; Oxford University Press: Oxford, U.K., 2006; Vol. 8.
83. Hübschle, C. B.; Sheldrick, G. M.; Dittrich, B. J. Appl. Crystallogr. 2011, 44, 1281-1284