Stereoelectronic effects in Menshutkin-type SN 2 reactions: theoretical study based on through-space/bond orbital interaction analysis
- 5 August 2013
- journal article
- research article
- Published by Wiley in Journal of Physical Organic Chemistry
- Vol. 26 (11), 885-891
- https://doi.org/10.1002/poc.3186
Abstract
No abstract availableKeywords
This publication has 32 references indexed in Scilit:
- Effect of Ionic Liquids on the Menschutkin Reaction: An Experimental and Theoretical StudyThe Journal of Organic Chemistry, 2009
- A New Insight into Using Chlorine Leaving Group and Nucleophile Carbon Kinetic Isotope Effects To Determine Substituent Effects on the Structure of SN2 Transition StatesThe Journal of Physical Chemistry A, 2007
- A Theoretical Study of Substituent Effects on Allylic Ion and Ion Pair SN2 ReactionsThe Journal of Organic Chemistry, 2005
- Own N-layered integrated molecular orbital and molecular mechanics study of the reaction of OH - with polychlorinated hydrocarbons CH (4-n) Cl n (n=2?4)Theoretical Chemistry Accounts, 2004
- Theoretical Study of the Anomeric Effect in CH2ClOHThe Journal of Physical Chemistry A, 2000
- RISM-SCF study of the free-energy profile of the Menshutkin-type reaction NH 3 +CH 3 Cl→NH 3 CH 3 + +Cl − in aqueous solutionTheoretical Chemistry Accounts, 1999
- The Menschutkin reaction of benzylp-toluenesulfonates withN,N-dimethylanilines. Evidence for the duality ofSN1 andSN2 mechanismsJournal of Physical Organic Chemistry, 1998
- Stereodependence of the Effect of α Substituents on the Face Reactivity of Conformationally Rigid Ketones toward Metal Hydrides. Is There an Antiperiplanar (Cieplak) Effect?The Journal of Organic Chemistry, 1997
- Steric and Stereoelectronic Control of the Mode Selectivity as a Function of Alkene Structure in the Reaction with Dimethyl α-Peroxy Lactone: Cycloadducts and Ene Products versus EpoxidesJournal of the American Chemical Society, 1996
- Stereoselective Cycloaddition and Epoxidation of Enol Ethers by α-Peroxy Lactone as a Function of Steric and Stereoelectronic EffectsThe Journal of Organic Chemistry, 1996