Local hardness: An application to electrophilic additions

L. Meneses; A. Araya; F. Pilaquinga; R. Contreras; P. Fuentealba

doi:10.1016/j.cplett.2007.07.092

Local hardness: An application to electrophilic additions

L. Meneses^*, A. Araya, F. Pilaquinga, R. Contreras, P. Fuentealba

^*Corresponding author for this work

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

25 Scopus citations

Abstract

The electrophilic addition of hydrogen chloride in substituted ethylenes has been revised by using the local hardness as a descriptor of selectivity. The regioselectivity shown by the local hardness values is in agreement with the empirical Markovnikov's rule. The effects of the electron-donating and electron-withdrawing substituents in the addition reactions have been studied in detail by calculating the energy of addition reaction and the activation energy for the transition states. It has been found that the strong electron-withdrawing substituents prefer to lead anti-Markovnikov products, while the electron-donating and weak electron-withdrawing groups prefer to form Markovnikov products.

Original language	English
Pages (from-to)	170-175
Number of pages	6
Journal	Chemical Physics Letters
Volume	446
Issue number	1-3
DOIs	https://doi.org/10.1016/j.cplett.2007.07.092
State	Published - 26 Sep 2007

Funding

This work was supported by DGA-PUCE grants C13039. The Millennium Nucleus for Applied Quantum Mechanics project P02-004-F, and FONDECYT Grants 1050294 and 1030548 supported part of this work.

Funders	Funder number
PUCE-DGA	C13039
Fondo Nacional de Desarrollo Científico y Tecnológico	1030548, 1050294

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10.1016/j.cplett.2007.07.092

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title = "Local hardness: An application to electrophilic additions",

abstract = "The electrophilic addition of hydrogen chloride in substituted ethylenes has been revised by using the local hardness as a descriptor of selectivity. The regioselectivity shown by the local hardness values is in agreement with the empirical Markovnikov's rule. The effects of the electron-donating and electron-withdrawing substituents in the addition reactions have been studied in detail by calculating the energy of addition reaction and the activation energy for the transition states. It has been found that the strong electron-withdrawing substituents prefer to lead anti-Markovnikov products, while the electron-donating and weak electron-withdrawing groups prefer to form Markovnikov products.",

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T2 - An application to electrophilic additions

AU - Meneses, L.

AU - Araya, A.

AU - Pilaquinga, F.

AU - Contreras, R.

AU - Fuentealba, P.

PY - 2007/9/26

Y1 - 2007/9/26

N2 - The electrophilic addition of hydrogen chloride in substituted ethylenes has been revised by using the local hardness as a descriptor of selectivity. The regioselectivity shown by the local hardness values is in agreement with the empirical Markovnikov's rule. The effects of the electron-donating and electron-withdrawing substituents in the addition reactions have been studied in detail by calculating the energy of addition reaction and the activation energy for the transition states. It has been found that the strong electron-withdrawing substituents prefer to lead anti-Markovnikov products, while the electron-donating and weak electron-withdrawing groups prefer to form Markovnikov products.

AB - The electrophilic addition of hydrogen chloride in substituted ethylenes has been revised by using the local hardness as a descriptor of selectivity. The regioselectivity shown by the local hardness values is in agreement with the empirical Markovnikov's rule. The effects of the electron-donating and electron-withdrawing substituents in the addition reactions have been studied in detail by calculating the energy of addition reaction and the activation energy for the transition states. It has been found that the strong electron-withdrawing substituents prefer to lead anti-Markovnikov products, while the electron-donating and weak electron-withdrawing groups prefer to form Markovnikov products.

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DO - 10.1016/j.cplett.2007.07.092

M3 - Article

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VL - 446

SP - 170

EP - 175

JO - Chemical Physics Letters

JF - Chemical Physics Letters

IS - 1-3

ER -

Local hardness: An application to electrophilic additions

Abstract

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