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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

The first binucleating amino-thiophenolate macrocycles with pendant hydroxyethyl groups.

Mathias Gressenbuch1, Berthold Kersting

  • 1Institut für Anorganische Chemie, Universität Leipzig, D-04103, Leipzig, Germany.

Dalton Transactions (Cambridge, England : 2003)
|July 1, 2009
PubMed
Summary

Researchers synthesized novel macrocyclic amino-thiophenolate ligands with multiple hydroxyethyl arms. Crystal structures of the ligands and a nickel-sodium complex were determined.

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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Area of Science:

  • Coordination Chemistry
  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Macrocyclic ligands are crucial in coordination chemistry for stabilizing metal ions.
  • Amino-thiophenolate ligands offer unique donor properties for metal complexation.
  • Functionalization with hydroxyethyl arms allows for tailored solubility and further modification.

Purpose of the Study:

  • To synthesize novel pendant donor macrocyclic amino-thiophenolate ligands.
  • To investigate the structural characteristics of these ligands and their metal complexes.
  • To explore the coordination behavior of amino-thiophenolate macrocycles with multiple functional arms.

Main Methods:

  • Multi-step organic synthesis for ligand preparation.
  • Single-crystal X-ray diffraction for structural determination of proligands and metal complexes.
  • Deprotection strategies to yield the final active ligands.

Main Results:

  • Successful synthesis of macrocyclic amino-thiophenolate ligands with up to six hydroxyethyl arms.
  • Determination of crystal structures for two distinct proligands.
  • Characterization of a Ni(2)Na(4) complex derived from a deprotected ligand, revealing its coordination environment.

Conclusions:

  • The study demonstrates a viable route to functionalized amino-thiophenolate macrocycles.
  • The reported crystal structures provide valuable insights into the solid-state architecture of these ligand systems.
  • The formation of the Ni(2)Na(4) complex highlights the potential of these ligands in constructing polynuclear metal assemblies.