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

Xi-Guang Wei; Xiao-Ming Sun; Xiao-Peng Wu; Yi Ren; Ning-Bew Wong; Wai-Kee Li

doi:10.1021/jo1006575

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

Xi-Guang Wei
, Xiao-Ming Sun
, Xiao-Peng Wu
, Yi Ren
, Ning-Bew Wong
, Wai-Kee Li

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

31 Citations (Scopus)

Abstract

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. © 2010 American Chemical Society.

Original language	English
Pages (from-to)	4212-4217
Journal	Journal of Organic Chemistry
Volume	75
Issue number	12
DOIs	https://doi.org/10.1021/jo1006575
Publication status	Published - 18 Jun 2010

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@article{e0b28d7c42964d6daebb0a0593868c66,

title = "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",

abstract = "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. {\textcopyright} 2010 American Chemical Society.",

author = "Xi-Guang Wei and Xiao-Ming Sun and Xiao-Peng Wu and Yi Ren and Ning-Bew Wong and Wai-Kee Li",

year = "2010",

month = jun,

day = "18",

doi = "10.1021/jo1006575",

language = "English",

volume = "75",

pages = "4212--4217",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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}

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. / Wei, Xi-Guang; Sun, Xiao-Ming; Wu, Xiao-Peng et al.
In: Journal of Organic Chemistry, Vol. 75, No. 12, 18.06.2010, p. 4212-4217.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

TY - JOUR

T1 - 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

AU - Wei, Xi-Guang

AU - Sun, Xiao-Ming

AU - Wu, Xiao-Peng

AU - Ren, Yi

AU - Wong, Ning-Bew

AU - Li, Wai-Kee

PY - 2010/6/18

Y1 - 2010/6/18

N2 - 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. © 2010 American Chemical Society.

AB - 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. © 2010 American Chemical Society.

UR - https://www.scopus.com/pages/publications/77953490104

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-77953490104&origin=recordpage

U2 - 10.1021/jo1006575

DO - 10.1021/jo1006575

M3 - RGC 21 - Publication in refereed journal

C2 - 20481599

SN - 0022-3263

VL - 75

SP - 4212

EP - 4217

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

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

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