Next Article in Journal
Substituent Inductive Effects on the Electrochemical Oxidation of Flavonoids Studied by Square Wave Voltammetry and Ab Initio Calculations
Next Article in Special Issue
Statistical Significance of the Maximum Hardness Principle Applied to Some Selected Chemical Reactions
Previous Article in Journal
Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs
Previous Article in Special Issue
Theoretical Study on Regioselectivity of the Diels-Alder Reaction between 1,8-Dichloroanthracene and Acrolein
Article Menu
Issue 11 (November) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(11), 1434; doi:10.3390/molecules21111434

A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σp in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives

1
Laboratoire de Chimie Analytique et Moléculaire, Faculté Polydisciplinaire de Safi, Université Cadi Ayyad, Safi 46010, Morocco
2
Departamento de Química Orgánica, Universidad de Valencia, Avda. Dr. Moliner 50, Burjassot 46100, Valencia, Spain
3
Instituto de Ciencia Molecular/ICMol, Universidad de Valencia, C/Catedrático José Beltrán No. 2, Paterna 46980, Valencia, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: James W. Gauld
Received: 14 August 2016 / Revised: 14 October 2016 / Accepted: 21 October 2016 / Published: 27 October 2016
View Full-Text   |   Download PDF [1257 KB, uploaded 27 October 2016]   |  

Abstract

The relationship between the electrophilicity ω index and the Hammett constant σp has been studied for the [2+3] cycloaddition reactions of a series of para-substituted phenyl azides towards para-substituted phenyl alkynes. The electrophilicity ω index—a reactivity density functional theory (DFT) descriptor evaluated at the ground state of the molecules—shows a good linear relationship with the Hammett substituent constants σp. The theoretical scale of reactivity correctly explains the electrophilic activation/deactivation effects promoted by electron-withdrawing and electron-releasing substituents in both azide and alkyne components. View Full-Text
Keywords: [2+3] cycloaddition reactions; arylazides; arylalkynes; substituent effects; electrophilicity index; Hammett constants [2+3] cycloaddition reactions; arylazides; arylalkynes; substituent effects; electrophilicity index; Hammett constants
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Ben El Ayouchia, H.; Anane, H.; El Idrissi Moubtassim, M.L.; Domingo, L.R.; Julve, M.; Stiriba, S.-E. A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σp in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives. Molecules 2016, 21, 1434.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top