Symmetry analysis in mechanistic studies of nucleophilic substitution and β-elimination reactions

Symmetry

Volumn 2, Issue 1, 2010, Pages 201-212

  Sun, Xiaoping ^a  

^a Robert C Byrd Center for Pharmacy Education   (United States)

Author keywords

E2 reaction; Electrophilicity; Molecular orbital (MO); S N2 reaction; Symmetry

Indexed keywords

EID: 84860466930     PISSN: None     EISSN: 20738994     Source Type: Journal    
DOI: 10.3390/sym2010201     Document Type: Article

References (18)

1. Fox, M.A.; Whitesell, J.K. Core Organic Chemistry; Jones and Bartlett Publishers: Boston, MA, USA, 1997; pp. 385-484.
2. Carey, F.A. Organic Chemistry, 5th ed.; McGraw-Hill: New York, NY, USA, 2003; pp. 326-362.
3. McMurry, J. Organic Chemistry, 6th ed.; Brooks/Cole: Belmont, CA, USA, 2004; pp. 343-392.
4. Reingold, I.D. Organic Chemistry: Am Introduction Emphasizing Biological Connections; Houghton Mifflin Company: Boston, MA, USA, 2002; pp. 310-320.
5. Brown, W.H.; Foote, C.S.; Iverson, B.L.; Anslyn, E.V. Organic Chemistry, 5th ed.; Brooks/Cole: Belmont, CA, USA, 2009; pp. 321-373.
6. 2+. J. Am. Chem. Soc. 1985, 107, 7423-7431.
7. Harcourt, R.D. Increased-valence structures and hypervalent molecules. Int. J. Quantum Chem. 1996, 60, 553-566.
8. Pross, A. The single electron shift as a fundamental process in organic chemistry: The relationship between polar and electron-transfer pathways. Acc. Chem. Res. 1985, 18, 212-219.
9. Shaik, S.S. The lego way: Curve crossing diagrams as general models in physical organic chemistry. Pure Appl. Chem. 1991, 63, 195-204.
10. Shaik, S.S.; Schlegel, H.B.; Wolfe, S. Theoretical Aspects of Physical Organic Chemistry: The SN2 Mechanism; Wiley: New York, NY, USA, 1992.
11. N2 mechanism by symmetry rules and qualitative molecular orbital theory. Chem. Educator 2003, 8, 303-306.
12. Huheey, J.E.; Keiter, E.A.; Keiter, R.L. Inorganic Chemistry: Principles of Structure and Reactivity, 4th ed.; Harper Collins: New York, NY, USA, 1993; pp. 53-63; 413-433; A-13-A-20.
13. 4. J. Am. Chem. Soc. 1978, 100, 2340-2345.
14. 5. J. Am. Chem. Soc. 1978, 100, 2346-2353.
15. 6. J. Am. Chem. Soc. 1978, 100, 2334-2339.
16. 2F. The role of the base as a catalyst. J. Am. Chem. Soc. 1993, 115, 9160-9173.
17. Ensing B.; Laio, A.; Gervasio, F.L.; Parrinello, M.; Klein, M.L. A minimum free energy reaction path for the E2 reaction between fluoro ethane and a floride ion. J. Am. Chem. Soc. 2004, 126, 9492-9493.
18. Bruckner, R. Advance Organic Chemistry: Reaction Mechanisms; Harcourt: San Diego, CA, USA, 2002; pp. 129-167.