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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.4K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.4K
Hydrogen Bonds01:04

Hydrogen Bonds

11.8K
A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
11.8K
Hydrogen Bonds00:26

Hydrogen Bonds

109.2K
Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
109.2K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.4K
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...
3.4K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

7.3K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
7.3K
Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

6.3K
Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates...
6.3K

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Anion recognition with hydrogen-bonding cyclodiphosphazanes.

Helge Klare1, Sebastian Hanft, Jörg M Neudörfl

  • 1Institut für Organische Chemie, Universität zu Köln, Greinstrasse 4, 50939 Köln (Germany).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 1, 2014
PubMed
Summary

New cyclodiphosphazanes show high affinity for anions like chloride. These compounds, particularly those with CF3 groups, demonstrate enhanced binding capabilities compared to traditional bisaryl urea receptors, paving the way for novel anion sensing materials.

Keywords:
X-ray diffractionanion recognitiondensity functional calculationshydrogen bondingphosphazanes

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Ion Mobility-Mass Spectrometry Techniques for Determining the Structure and Mechanisms of Metal Ion Recognition and Redox Activity of Metal Binding Oligopeptides
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Ion Mobility-Mass Spectrometry Techniques for Determining the Structure and Mechanisms of Metal Ion Recognition and Redox Activity of Metal Binding Oligopeptides
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Ion Mobility-Mass Spectrometry Techniques for Determining the Structure and Mechanisms of Metal Ion Recognition and Redox Activity of Metal Binding Oligopeptides

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Area of Science:

  • Supramolecular Chemistry
  • Organophosphorus Chemistry
  • Anion Recognition

Background:

  • Bisaryl urea derivatives are established receptors for anion binding.
  • Cyclodiphosphazanes represent a novel class of modular compounds with potential anion binding properties.
  • Understanding the structural and electronic factors influencing anion affinity is crucial for designing effective receptors.

Purpose of the Study:

  • To synthesize modular cyclodiphosphazanes and evaluate their anion binding affinities.
  • To compare the chloride and acetate binding affinities of novel cyclodiphosphazanes with a known bisaryl urea derivative.
  • To elucidate the structural and electronic factors governing the anion recognition capabilities of these compounds.

Main Methods:

  • Synthesis of cis-diamidocyclodiphosphazanes via reaction of a dichlorocyclodiphosphazane with anilines, followed by oxidation.
  • Characterization using multinuclear NMR spectroscopy, FTIR spectroscopy, high-resolution mass spectrometry, and single-crystal X-ray diffraction.
  • Determination of anion binding constants (log[K]) through binding studies and computational analysis (DFT).

Main Results:

  • Two novel cyclodiphosphazanes, cis-[{ArNHP(O)(μ-tBu)}2 ] with Ar=Ph (2) and Ar=m-(CF3 )2 Ph (3), were successfully synthesized and characterized.
  • Cyclodiphosphazane 3 exhibited significantly higher affinity for chloride (log[K]=5.42) compared to the bisaryl urea derivative 1 (log[K]=4.25).
  • Both compounds showed comparable affinities for acetate, while cyclodiphosphazane 2 (without CF3 groups) displayed weaker binding to both anions.

Conclusions:

  • The synthesized cyclodiphosphazanes are effective anion receptors, with fluorinated derivative 3 showing superior chloride binding.
  • Squaramide-like hydrogen bonding directionality and Cα-H···anion interactions are key to the high efficiency of cyclodiphosphazane 3.
  • These findings highlight the potential of modular cyclodiphosphazanes as advanced materials for anion recognition and sensing applications.