Nucleophilicity and Leaving-Group Ability in Frontside and Backside SN2 Reactions

2008 ◽  
Vol 73 (18) ◽  
pp. 7290-7299 ◽  
Author(s):  
A. Patrícia Bento ◽  
F. Matthias Bickelhaupt
Keyword(s):  
Sn2 Reactions ◽  
Leaving Group ◽  
Leaving Group Ability

Leaving group ability in base-promoted alkene-forming 1,2-eliminations

1975 ◽  
pp. 940 ◽  
Author(s):  
Donald R. Marshall ◽  
Patsy J. Thomas ◽  
Charles J. M. Stirling
Keyword(s):  
Leaving Group ◽  
Leaving Group Ability

Effect of the Leaving Group on the Rates of SN2 and SN2' Reactions in Allylic Systems

1960 ◽  
Vol 82 (11) ◽  
pp. 2881-2888 ◽  
Author(s):  
F. G. Bordwell ◽  
Phillip E. Sokol ◽  
James D. Spainhour
Keyword(s):  
Sn2 Reactions ◽  
Leaving Group

scholarly journals Leaving Group Ability in Nucleophilic Aromatic Amination by Sodium Hydride–Lithium Iodide Composite

Synthesis ◽  
2019 ◽  
Vol 52 (03) ◽  
pp. 393-398
Author(s):  
Jia Hao Pang ◽  
Derek Yiren Ong ◽  
Kohei Watanabe ◽  
Ryo Takita ◽  
Shunsuke Chiba
Keyword(s):  
Nucleophilic Substitution ◽  
Methoxy Group ◽  
Sodium Hydride ◽  
Lithium Iodide ◽  
Substitution Reactions ◽  
Computational Approaches ◽  
Nucleophilic Substitution Reactions ◽  
Leaving Group ◽  
Leaving Group Ability

The methoxy group is generally considered as a poor leaving group for nucleophilic substitution reactions. This work verified the superior ability of the methoxy group in nucleophilic amination of arenes mediated by the sodium hydride and lithium iodide through experimental and computational approaches.

Mechanisms of aromatic nucleophilic substitution by the ambident thiocyanate ion

1973 ◽  
Vol 26 (2) ◽  
pp. 273 ◽  
Author(s):  
DE Giles ◽  
AJ Parker
Keyword(s):  
Nucleophilic Substitution ◽  
Transition States ◽  
Reactivity Ratio ◽  
Substitution Reactions ◽  
Aromatic Nucleophilic Substitution ◽  
Thiocyanate Ion ◽  
Sn2 Reactions ◽  
Leaving Group ◽  
Electrophilic Reactivity ◽  
Saturated Carbon Atom

Sulphur/nitrogen reactivity ratios in a series of aromatic nucleophilic substitution reactions of ambident thiocyanate ion have been determined. There are profound differences from the pattern found in SN2 reactions at a saturated carbon atom. Abnormal transition states, involving interactions between entering and leaving group, are likely in the bond-breaking step of the intermediate complex in reactions of thiocyanate ion with 1-fluoro-2,4-dinitrobenzene and with 2,4- dinitrophenyl 4-toluenesulphonate. The nitro-substituted aryl thiocyanates are shown to be tri-functional electrophiles, with reactive centres at aromatic carbon, at cyanide carbon, and at sulphur. Aryl 4-toluenesulphonates are bifunctional electrophiles with reactive centres at aryl carbon and sulphonyl sulphur. The site of attack by nucleophiles depends on the nature of the nucleophile. The sulphur/nitrogen reactivity ratio of ambident SCN-, and the electrophilic reactivity of tri- and bi-functional substrates, are in most instances consistent with the Hard and Soft Acids and Bases principle. Exceptions to the principle in some instances reveal differences between the SNAr and SN2 mechanisms, and in others indicate abnormal transition states.

scholarly journals Nucleophilic substitution at di- and triphosphates: leaving group ability of phosphate versus diphosphate

2019 ◽  
Vol 1 (2) ◽  
pp. 024001 ◽  
Author(s):  
Bas van Beek ◽  
Marc A van Bochove ◽  
Trevor A Hamlin ◽  
F Matthias Bickelhaupt
Keyword(s):  
Nucleophilic Substitution ◽  
Leaving Group ◽  
Leaving Group Ability
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