Enhanced Reactivity of RCCZ− (R = H and Cl; Z = O, S, and Se) and the Influence of Leaving Group on the α-Effect in the E2 Reactions

The enhanced reactivity exhibited by six pseudo-α-bases, RCCZ− (R = H and Cl; Z = O, S, and Se) in gas-phase E2 reactions with ethyl chloride was examined at the G2(+) level. It is found that anomalous reactivity is observed despite the fact that these chalcogen bases do not possess adjacent lone-p...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2010-06, Vol.75 (12), p.4212-4217
Main Authors: Wei, Xi-Guang, Sun, Xiao-Ming, Wu, Xiao-Peng, Ren, Yi, Wong, Ning-Bew, Li, Wai-Kee
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Chlorine - chemistry
Ethyl Chloride - chemistry
Exact sciences and technology
Gases - chemistry
Hydrogen - chemistry
Kinetics and mechanisms
Molecular Structure
Organic chemistry
Oxygen - chemistry
Reactivity and mechanisms
Selenium - chemistry
Sulfur - chemistry
Thermodynamics
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The enhanced reactivity exhibited by six pseudo-α-bases, RCCZ− (R = H and Cl; Z = O, S, and Se) in gas-phase E2 reactions with ethyl chloride was examined at the G2(+) level. It is found that anomalous reactivity is observed despite the fact that these chalcogen bases do not possess adjacent lone-pair electrons. The influence of the halide leaving groups on the α-effect and the origin of the α-effect in the E2 reactions of ethyl halides are investigated and discussed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1006575