Enhanced reactivity of RC[triple bond]CZ- (R = H and Cl; Z = O, S, and Se) and the influence of leaving group on the alpha-effect in the E2 reactions.
The enhanced reactivity exhibited by six pseudo-alpha-bases, RC[triple bond]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 alpha-effect and the origin of the alpha-effect in the E2 reactions of ethyl halides are investigated and discussed.
Wei
Xi-Guang
XG
College of Chemistry, and Key State Laboratory of Biotherapy, Sichuan University, Chengdu 610064, China.
Sun
Xiao-Ming
XM
Wu
Xiao-Peng
XP
Ren
Yi
Y
Wong
Ning-Bew
NB
Li
Wai-Kee
WK
D002713:Chlorine / Q000737:chemistry*; D005018:Ethyl Chloride / Q000737:chemistry; D005740:Gases / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*; D013816:Thermodynamics
D005740:Gases; D005018:Ethyl Chloride; D002713:Chlorine; D013455:Sulfur; D006859:Hydrogen; D012643:Selenium; D010100:Oxygen