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Organophosphorus Chemistry: A New Perspective, 2nd Edition
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Organophosphorus Chemistry: A New Perspective, 2nd Edition

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 June 2024) | Viewed by 6262

Special Issue Editor

Dr. Jakub Adamek

E-Mail Website
Guest Editor
1. Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland
2. Biotechnology Center of Silesian University of Technology, B. Krzywoustego 8, 44-100 Gliwice, Poland
Interests: organic synthesis; electroorganic synthesis; organophosphorus chemistry; phosphonium salts; amino acids; NMR; IR
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

After the great success of the first edition, we are pleased to inform you that Molecules will launch the second edition of the Special Issue “Organophosphorus Chemistry: A New Perspective”.

https://www.mdpi.com/journal/molecules/special_issues/organophosphorus_chemistry_perspective.

Organophosphorus chemistry is undoubtedly important and one of the fastest-growing branches of organic chemistry. It is often said that we are now living in “the golden age of phosphorus chemistry”. In the laboratory, phosphorus-containing compounds (P-compounds) are widely used as reagents (starting materials, precursors of active intermediates, such as ylides or iminium-type cations, etc.), catalysts (PTC, organocatalysis), and solvents (PILs). Due to the interesting properties of P-compounds (especially their biological activity), they are used on a large scale in medicine (e.g., bone disorder drugs, anticancer and antiviral agents, or antihelminthics in veterinary applications), agriculture (e.g., pesticides), and industry (e.g., production of lubricants or plastic materials).

However, in the age of much-needed care for the natural environment, we face new challenges. Innovative approaches to the synthesis and isolation of P-compounds (taking into account the aspects of green chemistry and sustainability), followed by responsible use and disposal (neutralization), may prove crucial in the near future.

It is my great pleasure to invite experts in the field of organophosphorus chemistry to submit manuscripts in the form of short communications, full-length papers, and reviews to this Special Issue. I would like to extend a special invitation to young scientists to present their ideas and fresh approaches to the issues related to phosphorus chemistry.

Dr. Jakub Adamek
Guest Editor

Manuscript Submission Information

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. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short 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 thoroughly refereed through a single-blind 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 semimonthly journal published by MDPI.

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Keywords

  • organophosphorus chemistry
  • P-compounds
  • reactivity of P-compounds
  • new methods for the synthesis of P-compounds
  • P-C bond formation
  • phosphorus-based organocatalysis
  • phosphonium-based ionic liquids (PILs)
  • mitochondria-targeted triphenylphosphonium-based compounds
  • neutralization of P-compounds
  • chemical warfare agents
  • structure elucidation of P-compounds

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Related Special Issue

Published Papers (5 papers)

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Research

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8 pages, 1355 KiB  
Article
Towards Chemoenzymatic Syntheses of Both Enantiomers of Phosphoemeriamine
by Piotr Kiełbasiński, Małgorzata Kwiatkowska, Piotr Łyżwa and Marian Mikołajczyk
Molecules 2024, 29(8), 1799; https://doi.org/10.3390/molecules29081799 - 16 Apr 2024
Viewed by 741
Abstract
An enzyme-promoted addition of nitromethane to the appropriate phosphorylated imine (aza-Henry reaction) intended to be used in the synthesis of the title phosphoemeriamine, a phospha-analog of emeriamine (aminocarnitine), failed due to the tautomerization of the imine to the corresponding enamine. Nevertheless, both enantiomers [...] Read more.
An enzyme-promoted addition of nitromethane to the appropriate phosphorylated imine (aza-Henry reaction) intended to be used in the synthesis of the title phosphoemeriamine, a phospha-analog of emeriamine (aminocarnitine), failed due to the tautomerization of the imine to the corresponding enamine. Nevertheless, both enantiomers of phosphoemeriamine were synthesized in high yield and enantiomeric purity using another chemoenzymatic approach, starting with a crucial step involving a CAL-B-mediated acetylation of the appropriate racemic precursor—diethyl 2-amino-3-dimethylaminopropylphosphonate—under kinetic resolution conditions. The enzymatic reaction was very efficient and provided each enantiomeric product in acceptable yield and with enantiomeric excess of 91 and 92%. The following appropriate chemical transformations led to the desired enantiomers of phosphoemeriamine in the form of phosphoemeriamine sesquichloride with enantiomeric excess up to 90%. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry: A New Perspective, 2nd Edition)
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25 pages, 2974 KiB  
Article
Diastereoselective ZnCl2-Mediated Joullié–Ugi Three-Component Reaction for the Preparation of Phosphorylated N-Acylaziridines from 2H-Azirines
by Julene Allende, Iurre Olaizola, Ana M. Ochoa de Retana, Francisco Palacios and Jesús M. de los Santos
Molecules 2024, 29(5), 1023; https://doi.org/10.3390/molecules29051023 - 27 Feb 2024
Viewed by 1008
Abstract
We disclose a direct approach to the diastereoselective synthesis of phosphorus substituted N-acylaziridines based on a one-pot ZnCl2-catalyzed Joullié–Ugi three-component reaction of phosphorylated 2H-azirines, carboxylic acids and isocyanides. Hence, this robust protocol offers rapid access to an array [...] Read more.
We disclose a direct approach to the diastereoselective synthesis of phosphorus substituted N-acylaziridines based on a one-pot ZnCl2-catalyzed Joullié–Ugi three-component reaction of phosphorylated 2H-azirines, carboxylic acids and isocyanides. Hence, this robust protocol offers rapid access to an array of N-acylaziridines in moderate-to-good yields and up to 98:2 dr for substrates over a wide scope. The relevance of this synthetic methodology was achieved via a gram-scale reaction and the further derivatization of the nitrogen-containing three-membered heterocycle. The diastereo- and regioselective ring expansion of the obtained N-acylaziridines to oxazole derivatives was accomplished in the presence of BF3·OEt2 as an efficient Lewid acid catalyst. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry: A New Perspective, 2nd Edition)
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18 pages, 4121 KiB  
Article
1-Hydroxyalkylphosphonium Salts—Synthesis and Properties
by Jakub Adamek, Anna Kuźnik, Agnieszka Październiok-Holewa, Mirosława Grymel, Dominika Kozicka, Dominika Mierzwa and Karol Erfurt
Molecules 2024, 29(1), 18; https://doi.org/10.3390/molecules29010018 - 19 Dec 2023
Viewed by 1244
Abstract
An efficient and convenient method for the synthesis of 1-hydroxyalkylphosphonium salts is described. Reactions were carried out at room temperature, in a short time, and without chromatography for product isolation. The properties of the obtained phosphonium salts were examined and discussed. In this [...] Read more.
An efficient and convenient method for the synthesis of 1-hydroxyalkylphosphonium salts is described. Reactions were carried out at room temperature, in a short time, and without chromatography for product isolation. The properties of the obtained phosphonium salts were examined and discussed. In this paper, primary attention was paid to the stability of phosphonium salts, depending on the structure of the aldehydes used as substrates in their preparation. Other conditions such as the type of solvent, temperature, and molar ratio of the substrates were also investigated. Finally, the high reactivity of 1-hydroxyalkylphosphonium salts was demonstrated in reactions with amide-type substrates and (hetero)aromatic compounds. The developed step-by-step procedure (with the isolation of 1-hydroxyphosphonium salts) was compared to the one-pot protocol (in situ formation of such phosphonium salts). Full article
(This article belongs to the Special Issue Organophosphorus Chemistry: A New Perspective, 2nd Edition)
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27 pages, 2435 KiB  
Article
Phosphorus Chemistry at the Roots of Bioenergetics: Ligand Permutation as the Molecular Basis of the Mechanism of ATP Synthesis/Hydrolysis by FOF1-ATP Synthase
by Sunil Nath
Molecules 2023, 28(22), 7486; https://doi.org/10.3390/molecules28227486 - 8 Nov 2023
Cited by 6 | Viewed by 1326
Abstract
The integration of phosphorus chemistry with the mechanism of ATP synthesis/hydrolysis requires dynamical information during ATP turnover and catalysis. Oxygen exchange reactions occurring at β-catalytic sites of the FOF1-ATP synthase/F1-ATPase imprint a unique record of molecular events [...] Read more.
The integration of phosphorus chemistry with the mechanism of ATP synthesis/hydrolysis requires dynamical information during ATP turnover and catalysis. Oxygen exchange reactions occurring at β-catalytic sites of the FOF1-ATP synthase/F1-ATPase imprint a unique record of molecular events during the catalytic cycle of ATP synthesis/hydrolysis. They have been shown to provide valuable time-resolved information on enzyme catalysis during ATP synthesis and ATP hydrolysis. The present work conducts new experiments on oxygen exchange catalyzed by submitochondrial particles designed to (i) measure the relative rates of Pi–ATP, Pi–HOH, and ATP–HOH isotope exchanges; (ii) probe the effect of ADP removal on the extent of inhibition of the exchanges, and (iii) test their uncoupler sensitivity/resistance. The objectives have been realized based on new experiments on submitochondrial particles, which show that both the Pi–HOH and ATP–HOH exchanges occur at a considerably higher rate relative to the Pi–ATP exchange, an observation that cannot be explained by previous mechanisms. A unifying explanation of the kinetic data that rationalizes these observations is given. The experimental results in (ii) show that ADP removal does not inhibit the intermediate Pi–HOH exchange when ATP and submitochondrial particles are incubated, and that the nucleotide requirement of the intermediate Pi–HOH exchange is adequately met by ATP, but not by ADP. These results contradicts the central postulate in Boyer’s binding change mechanism of reversible catalysis at a F1 catalytic site with Keq~1 that predicts an absolute requirement of ADP for the occurrence of the Pi–HOH exchange. The prominent intermediate Pi–HOH exchange occurring under hydrolytic conditions is shown to be best explained by Nath’s torsional mechanism of energy transduction and ATP synthesis/hydrolysis, which postulates an essentially irreversible cleavage of ATP by mitochondria/particles, independent from a reversible formation of ATP from ADP and Pi. The explanation within the torsional mechanism is also shown to rationalize the relative insensitivity of the intermediate Pi–HOH exchange to uncouplers observed in the experiments in (iii) compared to the Pi–ATP and ATP–HOH exchanges. This is shown to lead to new concepts and perspectives based on ligand displacement/substitution and ligand permutation for the elucidation of the oxygen exchange reactions within the framework of fundamental phosphorus chemistry. Fast mechanisms that realize the rotation/twist, tilt, permutation and switch of ligands, as well as inversion at the γ-phosphorus synchronously and simultaneously and in a concerted manner, have been proposed, and their stereochemical consequences have been analyzed. These considerations take us beyond the binding change mechanism of ATP synthesis/hydrolysis in bioenergetics. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry: A New Perspective, 2nd Edition)
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Review

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28 pages, 9422 KiB  
Review
Comprehensive Review of Synthesis, Optical Properties and Applications of Heteroarylphosphonates and Their Derivatives
by Krzysztof Owsianik, Adrian Romaniuk, Marika Turek and Piotr Bałczewski
Molecules 2024, 29(15), 3691; https://doi.org/10.3390/molecules29153691 - 4 Aug 2024
Viewed by 1152
Abstract
This review focuses on optical properties of compounds in which at least one phosphonate group is directly attached to a heteroaromatic ring. Additionally, the synthesis and other applications of these compounds are addressed in this work. The influence of the phosphonate substituent on [...] Read more.
This review focuses on optical properties of compounds in which at least one phosphonate group is directly attached to a heteroaromatic ring. Additionally, the synthesis and other applications of these compounds are addressed in this work. The influence of the phosphonate substituent on the properties of the described compounds is discussed and compared with other non-phosphorus substituents, with particular attention given to photophysical properties, such as UV-Vis absorption and emission, fluorescence quantum yield and fluorescence lifetime. Considering the presence of heteroatom, the collected material was divided into two parts, and a review of the literature of the last thirty years on heteroaryl phosphonates containing sulfur and nitrogen atoms in the aromatic ring was conducted. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry: A New Perspective, 2nd Edition)
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