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Special Issue "Electrophilic & Nucleophilic Substitution"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 May 2013)

Special Issue Editor

Guest Editor
Prof. Dr. Michael De Rosa (Website)

Department of Chemistry, Penn State Brandywine, 25 Yearsley Mill Road, Media, PA 19063, USA
Interests: pyrroles; aminopyrroles; electrophilic aromatic substitution by addition-elimination; electrophilic aromatic substitution; N-chlorination; inverse electron demand Diels-Alder reactions; S_N AR; tautomerism

Special Issue Information

Dear Colleagues,

In 1934, in a Chemical Society Chemical Reviews paper entitled “Principles of an electronic theory of organic reactions”, Ingold introduced the terms electrophilic and nucleophilic into chemistry. Since then they have become basic concepts used to explain electrophile-nucleophile combinations. Physical organic chemists have developed scales/equations to quantify these effects based on model reactions; electronic factors have been considered; more recently theoreticians have used density-functional theory (DFT) to create indices or descriptors of electrophilicity and nucleophilicity. This issue aims to bring together a representative sample of current experimental and theoretical work in this area.

Prof. Dr. Michael De Rosa
Guest Editor

Submission

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed Open Access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs).

Keywords

  • electrophilic substitution or addition
  • nucleophilic substitution or addition
  • electrophile-nucleophile combinations
  • superelectrophiles
  • scales/indices of electrophilicity and nucleophilicity
  • theoretical Studies

Published Papers (2 papers)

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Research

Open AccessArticle Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives
Molecules 2013, 18(9), 10254-10265; doi:10.3390/molecules180910254
Received: 3 June 2013 / Revised: 13 August 2013 / Accepted: 16 August 2013 / Published: 22 August 2013
Cited by 1 | PDF Full-text (412 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The nucleophilic character and stability of the carbanions vs. alkoxides derived from 2,2,2-trifluoro-1-(9-anthryl)ethanol and 1-(9-anthryl)ethanol containing X electron-releasing and X electron-acceptor substituents attached to C-10, have been studied at the B3LYP/6-31+G(d,p) level of theory. Results analyzed in terms of the absolute [...] Read more.
The nucleophilic character and stability of the carbanions vs. alkoxides derived from 2,2,2-trifluoro-1-(9-anthryl)ethanol and 1-(9-anthryl)ethanol containing X electron-releasing and X electron-acceptor substituents attached to C-10, have been studied at the B3LYP/6-31+G(d,p) level of theory. Results analyzed in terms of the absolute gas-phase acidity, Fukui function, the local hard and soft acids and bases principle, and the molecular electrostatic potential, show that the central ring of the 9-anthryl group confers an ambident nucleophilic character and stabilizes the conjugated carbanion by electron-acceptor delocalization. Full article
(This article belongs to the Special Issue Electrophilic & Nucleophilic Substitution)
Figures

Open AccessArticle Benchmark Study on the Smallest Bimolecular Nucleophilic Substitution Reaction: H−+CH4 →CH4+H
Molecules 2013, 18(7), 7726-7738; doi:10.3390/molecules18077726
Received: 20 May 2013 / Revised: 3 June 2013 / Accepted: 28 June 2013 / Published: 3 July 2013
Cited by 1 | PDF Full-text (373 KB) | HTML Full-text | XML Full-text
Abstract
We report here a benchmark study on the bimolecular nucleophilic substitution (SN2) reaction between hydride and methane, for which we have obtained reference energies at the coupled cluster toward full configuration-interaction limit (CC-cf/CBS). Several wavefunction (HF, MP2, coupled cluster) and [...] Read more.
We report here a benchmark study on the bimolecular nucleophilic substitution (SN2) reaction between hydride and methane, for which we have obtained reference energies at the coupled cluster toward full configuration-interaction limit (CC-cf/CBS). Several wavefunction (HF, MP2, coupled cluster) and density functional methods are compared for their reliability regarding these reference data. Full article
(This article belongs to the Special Issue Electrophilic & Nucleophilic Substitution)

Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Type of Paper: Review
Title: New Developments in the Asymmetric Additions to Cyclic Iminium Ions
Authors: Amalraj John 1, Oscar Forero-Doria 2 and Leonardo S. Santos 1,2
Affiliations: 1 Nanobiotechnology Division at University of Talca, Fraunhofer Chile Research Foundation - Center for Systems Biotechnology, FCR-CSB, P.O. Box 747, Talca, Maule, Chile
2 Chemistry Institute of Natural Resources, Universidad de Talca, Talca, Maule, Chile
Abstract:
The man’s fascination with chemical reactions goes back to ancient times. With the introduction of asymmetric methodologies, the art of developing reactions became an intriguing science. It is, therefore, not unexpected that one of the most prosperous and worthwhile frontiers in modern Chemistry is the study of new diastereoselective reactions. As man’s imagination does not stop at the frontiers defined by nature, and with the ever increasing power of catalysis, the synthetic organic chemist is poised to make important contributions by inventing and developing new enabling technologies for the production of new catalysts and asymmetric methodologies. In this review is offered to readers the best electrophile-nucleophile combinations to achieve chiral pyrrolidine, piperidine and other products derived from cyclic 5-, 6-, 7-membered iminium ion intermediates, which are synthons for the syntheses of several classes of important alkaloids.

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