Electron donor-acceptor (EDA)-complex enabled SF5Cl addition on alkenes and alkynes

The reversible, weak ground-state aggregate formed by dipole–dipole interactions between an electron donor and an electron acceptor is referred to as an electron-donor–acceptor (EDA) complex. Generally, upon light irradiation, the EDA complex turns into the excited state, causing an electron transfer to give radicals and to initiate subsequent reactions. Besides light as an external energy source, reactions involving the participation of EDA complexes are mild, obviating transition metal catalysts or photosensitizers in the majority of cases and are in line with the theme of green chemistry. This review discusses the synthetic reactions concerned with EDA complexes as well as the mechanisms that have been shown over the past five years.

Download Full-text

n–π Electron donor–acceptor complexes. II. Aliphatic amines with dinitrobenzenes

Canadian Journal of Chemistry ◽

10.1139/v85-150 ◽

1985 ◽

Vol 63 (4) ◽

pp. 903-907 ◽

Cited By ~ 26

Author(s):

Joaquín O. Singh ◽

Jorge D. Anunziata ◽

Juana J. Silber

Keyword(s):

Electron Donor ◽

Iterative Procedure ◽

Steric Effect ◽

Aliphatic Amines ◽

Primary Amines ◽

Substitution Reactions ◽

Aromatic Nucleophilic Substitution ◽

Donor Acceptor ◽

Eda Complex ◽

The Stability

The interaction of several aliphatic amines as n-donors and dinitrobenzenes (DNB) as π-acceptors has been studied in n-hexane. The formation of electron donor – acceptor (EDA) complexes is proposed to explain the spectroscopic behaviour of the mixtures. The stability constants (Ks) for these complexes have been calculated by an iterative procedure. For a given acceptor, the donor strength of RNH2 > R2NH > R3N was found. This order is explained by considering the role that steric effect may play in the EDA complex formation. On the other hand, the fact that for a given donor Ks follows the order 1,2-DNB > 1,3-DNB > 1,4-DNB, and that 1,2-DNB reacts with primary amines, led to the proposal of orientational complexes. These EDA complexes may be considered intermediates in aromatic nucleophilic substitution reactions.

Download Full-text

ChemInform Abstract: THE ELECTRONIC STRUCTURE OF THE ELECTRON-DONOR-ACCEPTOR SYSTEM IN THE EXCITED STATE, THE EXCIPLEX AND THE FLUORESCENT STATE OF EDA COMPLEX

Chemischer Informationsdienst ◽

10.1002/chin.197544083 ◽

1975 ◽

Vol 6 (44) ◽

Author(s):

TSUTOMU MIMURA ◽

MICHIYA ITOH ◽

TOSHIAKI OHTA ◽

TOSHIHIKO OKAMOTO

Keyword(s):

Electronic Structure ◽

Excited State ◽

Electron Donor ◽

Donor Acceptor ◽

Fluorescent State ◽

Eda Complex

Download Full-text

Visible-Light-Driven Electron Donor–Acceptor Complex Induced Sulfonylation of Diazonium Salts with Sulfinates

Green Chemistry ◽

10.1039/d1gc03239a ◽

2021 ◽

Author(s):

Xin Liang ◽

Yufei Li ◽

Qing Xia ◽

Lan Cheng ◽

Jianbo Guo ◽

...

Keyword(s):

Visible Light ◽

Electron Donor ◽

Coupling Reaction ◽

Diazonium Salts ◽

Acceptor Complex ◽

Radical Coupling ◽

Visible Light Driven ◽

Donor Acceptor ◽

Radical Coupling Reaction ◽

Eda Complex

This work reports an efficient sulfonylation enabled by visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor–acceptor (EDA) complex....

Download Full-text

The kinetics of formation of electron donor–acceptor complexes. A temperature-jump study

Canadian Journal of Chemistry ◽

10.1139/v90-038 ◽

1990 ◽

Vol 68 (2) ◽

pp. 278-281 ◽

Cited By ~ 4

Author(s):

M. A. Zon ◽

H. Fernandez ◽

L. Sereno ◽

J. J. Silber

Keyword(s):

Electron Donor ◽

Rate Constants ◽

Temperature Jump ◽

Diffusion Control ◽

Diffusion Controlled ◽

Kinetics Of Formation ◽

Donor Acceptor ◽

Eda Complex ◽

Kinetics Of

The kinetics of the Electron Donor–Acceptor (EDA) complex between N,N,N′,N′-tetramethyl-p-phenylenediamine and m-dinitrobenzene in acetonitrile has been studied by the temperature-jump technique. The magnitude of the rate constants of association and dissociation, although relatively large, is well below the diffusion control values. The calculated rates closely coincide with those obtained by chronoamperometry. An entropy control is suggested for this reaction. The results obtained in this work are useful to demonstrate that the concept about EDA complexes being formed by diffusion-controlled reactions should not be generalized. Keywords: electron donor–acceptor complexes, m-dinitrobenzene, N,N,N′,N′-tetramethyl-p-phenylenediamine, T-jump, kinetics.

Download Full-text