Computational study of bystander effects in the 1,2-H shifts of alkylmethylcarbenes

Ching Han Hu

doi:10.1016/S0166-1280(00)00395-X

Computational study of bystander effects in the 1,2-H shifts of alkylmethylcarbenes

Ching Han Hu

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

Bystander substituent effects in the 1,2-H shifts of several singlet alkylmethylcarbenes (CH₂Y-C-CH₃) have been studied using density functional theory. Bystander effects similar to that of alkylchlorocarbenes were observed. The methyl, halo, and phenyl groups accelerate 1,2-H shifts in the order Ph > F > Me > Cl, Br > H. Singlet/triplet energy separation of these carbenes have also been examined. All studied carbenes have singlet ground states, and the ability of Y groups to stabilize the relative energies of singlet states is F > Cl > Br> Ph > Me > H. (C) 2000 Elsevier Science B.V.

Original language	English
Pages (from-to)	39-49
Number of pages	11
Journal	Journal of Molecular Structure: THEOCHEM
Volume	531
Issue number	1-3
DOIs	https://doi.org/10.1016/S0166-1280(00)00395-X
Publication status	Published - 2000 Oct 23

All Science Journal Classification (ASJC) codes

Biochemistry
Condensed Matter Physics
Physical and Theoretical Chemistry

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10.1016/S0166-1280(00)00395-X

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abstract = "Bystander substituent effects in the 1,2-H shifts of several singlet alkylmethylcarbenes (CH2Y-C-CH3) have been studied using density functional theory. Bystander effects similar to that of alkylchlorocarbenes were observed. The methyl, halo, and phenyl groups accelerate 1,2-H shifts in the order Ph > F > Me > Cl, Br > H. Singlet/triplet energy separation of these carbenes have also been examined. All studied carbenes have singlet ground states, and the ability of Y groups to stabilize the relative energies of singlet states is F > Cl > Br> Ph > Me > H. (C) 2000 Elsevier Science B.V.",

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T1 - Computational study of bystander effects in the 1,2-H shifts of alkylmethylcarbenes

AU - Hu, Ching Han

PY - 2000/10/23

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N2 - Bystander substituent effects in the 1,2-H shifts of several singlet alkylmethylcarbenes (CH2Y-C-CH3) have been studied using density functional theory. Bystander effects similar to that of alkylchlorocarbenes were observed. The methyl, halo, and phenyl groups accelerate 1,2-H shifts in the order Ph > F > Me > Cl, Br > H. Singlet/triplet energy separation of these carbenes have also been examined. All studied carbenes have singlet ground states, and the ability of Y groups to stabilize the relative energies of singlet states is F > Cl > Br> Ph > Me > H. (C) 2000 Elsevier Science B.V.

AB - Bystander substituent effects in the 1,2-H shifts of several singlet alkylmethylcarbenes (CH2Y-C-CH3) have been studied using density functional theory. Bystander effects similar to that of alkylchlorocarbenes were observed. The methyl, halo, and phenyl groups accelerate 1,2-H shifts in the order Ph > F > Me > Cl, Br > H. Singlet/triplet energy separation of these carbenes have also been examined. All studied carbenes have singlet ground states, and the ability of Y groups to stabilize the relative energies of singlet states is F > Cl > Br> Ph > Me > H. (C) 2000 Elsevier Science B.V.

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