Factors affecting the relative stability of a series of iminium cation stereoisomers

Journal of Molecular Structure: THEOCHEM

Volumn 806, Issue 1-3, 2007, Pages 223-230

  Hsueh, Powen ^a   Lukowski, Mark ^a   Lindsay, Harriet A ^a   Milletti, M C ^a  

^a EASTERN MICHIGAN UNIVERSITY   (United States)

Author keywords

Conformation; Iminium cation; Molecular orbital; Stereochemistry

Indexed keywords

EID: 33846829560     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2006.11.031     Document Type: Article

References (25)

1. Maryanoff B.E., Zhang H.-C., Cohen J.H., Turchi I.J., and Maryanoff C.A. Chem. Rev. 104 (2004) 1431
2. Blumenkopf T.A., and Overman L.E. Chem. Rev. 86 (1986) 857
3. Overman L.E., and Ricca D.J. In: Heathcock C.H., Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 2 (1991), Pergamon, Oxford 1007
4. Overman L.E. Acc. Chem. Res. 25 (1992) 352
5. Overman L.E., Kakimoto M., Okazaki M.E., and Meier G.P. J. Am. Chem. Soc. 105 (1983) 622
6. Deng W., and Overman L.E. J. Am. Chem. Soc. 116 (1994) 11241
7. Overman L.E., and Trenkle W. Isr. J. Chem. 37 (1997) 23
8. Heintzelman G.R., Meigh I.R., Mahajan Y.R., and Weinreb S.M. Organic Reactions vol. 65 (2005), Wiley-VCH, New York 141
9. Lelais G., and MacMillan D.W.C. Aldrichimica Acta 39 (2006) 79
10. Iminium cation geometry is one of several factors influencing this relative stereochemistry For a comprehensive discussion of these issues, see References [5,6].
11. R Domingo L., Oliva M., and Andres J. J. Org. Chem. 66 (2001) 6151
12. Zora M. J. Mol. Struct. (Theochem) 619 (2002) 121
13. Kvaerno L., Norrby P.-O., and Tanner D. Org. Biomol. Chem. 1 (2003) 1041
14. Evans G.J.S., White K., Platts J.A., and Tomkinson N.C.O. Org. Biomol. Chem. 4 (2006) 2616
15. Gaussian 03, Revision C.02, 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, V. Bakken, 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. Gil, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford CT, 2004.
16. GaussView, Version 3.09, R. Dennington II, T. Keith, J. Millam, K. Eppinnett, W.L. Hovell, R. Gilliland, Semichem, Inc., Shawnee Mission, KS, 2003.
17. Becke A.D. J. Chem. Phys. 98 (1993) 5648
18. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
19. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200
20. McLean A.D., and Chandler G.S. J. Chem. Phys. 72 (1980) 5639
21. Krishnan R., Binkley J.S., Seeger R., and Pople J.A. J. Chem. Phys. 72 (1980) 650
22. Schlegel H.B. J. Comp. Chem. 3 (1984) 214
23. Schlegel H.B. In: Bertran J. (Ed). New Theoretical Concepts for Understanding Organic Reactions (1989), Kluwer Academic, The Netherlands 33-53
24. Schlegel H.B. In: Yarkony D.R. (Ed). Geometry Optimization on Potential Energy Surfaces, Modern Electronic Structure Theory (1994), World Scientific Publishing, Singapore
25. Foster J.P., and Weinhold F.J. J. Am. Chem. Soc. 102 (1980) 7211