Facial Selectivity of the (R)-1,3-Dimethyl-1-Cyclohexyl Cation in the Gas Phase

Chemistry - A European Journal

Volumn 9, Issue 21, 2003, Pages 5396-5403

  Filippi, Antonello ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Diastereoselectivity; Facial selectivity; Gas phase reactions; Ion molecule reactions; Kinetics; Noncovalent interactions

Indexed keywords

CHEMICAL ACTIVATION; KINETIC THEORY OF GASES; MATHEMATICAL MODELS; METHANOL; PROBABILITY DENSITY FUNCTION; RADIOLYSIS; SURFACE REACTIONS;

DENSITY FUNCTIONAL THEORY (DFT); GAS PHASE REACTIONS;

POSITIVE IONS;

CATION; FUNCTIONAL GROUP; METHANOL;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL REACTION; COVALENT BOND; ENTROPY; GAS; MOLECULAR DYNAMICS; MOLECULAR MODEL; PHASE TRANSITION; RADIOLYSIS;

EID: 0344927737     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304859     Document Type: Article

References (32)

1. Special Thematic Issue on Diastereoselection; Chem. Rev. 1999, 95, whole issue.
2. a) C. K. Cheung, L. T. Tseng, M. H. Lin, S. Srivastava, W. J. le Noble, J. Am. Chem. Soc. 1986, 108, 1598-1605; corrigendum: C. K. Cheung, L. T. Tseng, M. H. Lin, S. Srivastava, W. J. le Noble, J. Am. Chem. Soc. 1987, 109, 7239;
3. a) C. K. Cheung, L. T. Tseng, M. H. Lin, S. Srivastava, W. J. le Noble, J. Am. Chem. Soc. 1986, 108, 1598-1605; corrigendum: C. K. Cheung, L. T. Tseng, M. H. Lin, S. Srivastava, W. J. le Noble, J. Am. Chem. Soc. 1987, 109, 7239;
4. b) S. Srivastava, W. J. le Noble, J. Am. Chem. Soc. 1987, 109, 5874-5875;
5. c) W. Adcock, J. Cotton, N. A. Trout, J. Org. Chem. 1994, 59, 1867-1876;
6. d) R. Herrmann, W. Kirmse, Liebigs Ann. Chem. 1995, 699-702;
7. e) W. Adcock, N. J. Head, N. R. Lokan, N. A. Trout, J. Org. Chem. 1997, 62, 6177-6182.
8. A. Filippi, N. A. Trout, P. Brunelle, W. Adcock, T. S. Sorensen, M. Speranza, J. Am. Chem. Soc. 2001, 123, 6396-6403.
9. a) A. Rauk, T. S. Sorensen, C. Maerker, J. W. de M. Carneiro, S. Sieber, P. von R. Schleyer, J. Am. Chem. Soc. 1996, 118, 3761-3762;
10. b) A. Rauk, T. S. Sorensen, P. von R. Schleyer, J. Chem. Soc. Perkin Trans. 2 2001, 869-874.
11. -1;
12. -1.
13. R. J. Blint, T. B. McMahon, J. L. Beauchamp, J. Am. Chem. Soc. 1974, 96, 1269-1278.
14. -1 (ref. [5 a]).
15. Estimated according to: T. Su, W. J. Chesnavitch, J. Chem. Phys. 1982, 76, 5183-5185.
16. M. Speranza, A. Troiani, J. Org. Chem. 1998, 63, 1020-1026.
17. 18O label.
18. 18O (ca. 3 Torr).
19. 3.
20. a) A. D. Becke, J. Chem. Phys. 1993, 98, 1372-1377, 5648-5652;
21. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
22. a) E. L. Eliel, T. J. Brett, J. Am. Chem. Soc. 1965, 87, 5039-5043, and references therein;
23. b) F. R. Jensen, B. H. Beck, J. Am. Chem. Soc. 1968, 90, 1066-1067.
24. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, 2nd ed., Wiley-VCH, Weinheim, 1999.
25. E. C. Ashby, J. T. Laemmle, Chem. Rev. 1975, 75, 521-546.
26. a) A. S. Cieplack, B. D. Tait, C. R. Johnson, J. Am. Chem. Soc. 1989, 111, 8447-8462;
27. b) J. Hudec, J. Huke, J. W. Liebeschuetz, J. Chem. Soc. Perkin Trans. 2, 1998, 1129-1138.
28. M. Speranza, A. Filippi, G. Renzi, G. Roselli, F. Grandinetti, Chem. Eur. J. 2003, 9, 2072-2078.
29. The term troposelectivity has been recently coined (A. Filippi, M. Speranza, J. Am. Chem. Soc. 2001, 123, 6077-82). Strictly speaking it stands for the selectivity of a reagent toward the chiral or prochiral face of a substrate on which it has been generated. In light of the present work, troposelective reactions are as common as the occurrence of slowly interconverting FAs in the gas phase.
30. R. Greenwald, M. Chaykovsky, E. J. Corey, J. Org. Chem. 1963, 28, 1128-1129.
31. 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. Stratman, 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. Malik, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Raboul, B. B. Stefaniv, G. Liu, A. Liashenko, P. Piskorz, I. Nanayakkara, C. Gonzales, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzales, M. Head-Gordon, E. S. Replogle, J. A. Pople, GAUSSIAN 98, Revision A7, Gaussian Inc., Pittsburg, PA, 1998.
32. A. P. Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502-16513.