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Pure Appl. Chem., 2009, Vol. 81, No. 4, pp. 709-717

http://dx.doi.org/10.1351/PAC-CON-08-10-03

Steric and electronic effects in SN2 reactions

Einar Uggerud

Mass Spectrometry Laboratory and The Centre for Theoretical and Computational Chemistry (CTCC), Department of Chemistry, University of Oslo, P.O. Box 1033 Blindern, N-0315 Oslo, Norway

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  • Fernández Israel, Bickelhaupt F. Matthias, Uggerud Einar: Reactivity in Nucleophilic Vinylic Substitution (SNV):SNVπ versus SNVσ Mechanistic Dichotomy. J. Org. Chem. 2013, 78, 8574. <http://dx.doi.org/10.1021/jo401242f>
  • Li Qianbiao, Bao Yinyin, Wang Hu, Du Fanfan, Li Qing, Jin Bangkun, Bai Ruke: A facile and highly efficient strategy for esterification of poly(meth)acrylic acid with halogenated compounds at room temperature promoted by 1,1,3,3-tetramethylguanidine. Polym. Chem. 2013, 4, 2891. <http://dx.doi.org/10.1039/c3py00155e>
  • Kretschmer Robert, Schlangen Maria, Kaupp Martin, Schwarz Helmut: Neutral Metal Atoms Acting as a Leaving Group in Gas-Phase SN2 Reactions: M(CH3)+ + NH3 → CH3NH3+ + M (M = Zn, Cd, Hg). Organometallics 2012, 31, 3816. <http://dx.doi.org/10.1021/om300116c>
  • Kretschmer Robert, Schlangen Maria, Schwarz Helmut: Effiziente und selektive Monomethylierung kontra N-H-Bindungsaktivierung von Ammoniak: atomares Zink als Abgangsgruppe in einer SN2-Reaktion von “nacktem” Zn(CH3)+ und NH3. angew chemie 2011, 123, 5499. <http://dx.doi.org/10.1002/ange.201100096>
  • Schwarz Helmut, Kretschmer Robert, Schlangen Maria: Efficient and Selective Gas-Phase Monomethylation versus NH Bond Activation of Ammonia by “Bare” Zn(CH3)+: Atomic Zinc as a Leaving Group in an SN2 Reaction. Angew Chem Int E 2011, 50, 5387. <http://dx.doi.org/10.1002/anie.201100096>
  • Garver John M., Eyet Nicole, Villano Stephanie M., Yang Zhibo, Bierbaum Veronica M.: Mechanistic investigation of SN2 dominated gas phase alkyl iodide reactions. Int J Mass Spectrosc 2011, 301, 151. <http://dx.doi.org/10.1016/j.ijms.2010.08.008>
  • Garver John M., Gronert Scott, Bierbaum Veronica M.: Experimental Validation of the α-Effect in the Gas Phase. J Ann Chem Soc 2011, 133, 13894. <http://dx.doi.org/10.1021/ja205741m>
  • Garver John M., Fang Yao-ren, Eyet Nicole, Villano Stephanie M., Bierbaum Veronica M., Westaway Kenneth Charles: A Direct Comparison of Reactivity and Mechanism in the Gas Phase and in Solution. J Am Chem Soc 2010, 132, 3808. <http://dx.doi.org/10.1021/ja909399u>
  • Pierrefixe Simon C. A. H., van Stralen Sebastiaan J. M., van Stralen Joost N. P., Fonseca Guerra Célia, Bickelhaupt F. Matthias: Hypervalent Carbon Atom: “Freezing” the SN2 Transition State. Angew Chem 2009, 121, 6591. <http://dx.doi.org/10.1002/ange.200902125>
  • Pierrefixe Simon C. A. H., van Stralen Sebastiaan J. M., van Stralen Joost N. P., Fonseca Guerra Célia, Bickelhaupt F. Matthias: Hypervalent Carbon Atom: “Freezing” the SN2 Transition State. Angew Chem Int Ed 2009, 48, 6469. <http://dx.doi.org/10.1002/anie.200902125>
  • Uggerud Einar: ChemInform Abstract: Steric and Electronic Effects in SN2 Reactions. ChemInform 2009, 40. <http://dx.doi.org/10.1002/chin.200930275>