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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

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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 higher...
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Ions as Acids and Bases02:54

Ions as Acids and Bases

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Salts with Acidic Ions
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
26.9K
Hydrogen Bonds01:04

Hydrogen Bonds

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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...
15.5K
Hydrogen Bonds00:26

Hydrogen Bonds

135.7K
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....
135.7K
Relative Strengths of Conjugate Acid-Base Pairs02:29

Relative Strengths of Conjugate Acid-Base Pairs

53.2K
Brønsted-Lowry acid-base chemistry is the transfer of protons; thus, logic suggests a relation between the relative strengths of conjugate acid-base pairs. The strength of an acid or base is quantified in its ionization constant, Ka or Kb, which represents the extent of the acid or base ionization reaction. For the conjugate acid-base pair HA / A−, the ionization equilibrium equations and ionization constant expressions are
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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H-Bond Acceptor Parameters for Anions.

Sarah J Pike1, Jordan J Hutchinson2, Christopher A Hunter1

  • 1Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.

Journal of the American Chemical Society
|May 5, 2017
PubMed
Summary
This summary is machine-generated.

This study quantifies hydrogen-bonding strengths for various anions using UV/vis titrations. Anion H-bond parameters (β) are transferable across solvents and donors, enabling accurate prediction of anion recognition.

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Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry
  • Physical Organic Chemistry

Background:

  • Hydrogen bonding plays a crucial role in molecular recognition and self-assembly.
  • Quantifying the hydrogen-bond acceptor (HBA) strength of anions is essential for understanding their interactions in solution.
  • Previous studies have often focused on specific anion-donor pairs or limited solvent systems.

Purpose of the Study:

  • To systematically investigate and quantify the hydrogen-bond acceptor (HBA) parameters (β) for a diverse set of 15 anions.
  • To assess the transferability of these HBA parameters across different neutral hydrogen-bond donors (HBDs) and organic solvents (chloroform and acetonitrile).
  • To establish a reliable method for predicting anion recognition properties in various chemical environments.

Main Methods:

  • Utilizing UV/vis absorption titrations to monitor the formation of hydrogen-bonded complexes between anions and neutral HBDs.
  • Employing a series of 15 different anions and 3 distinct HBDs in both chloroform and acetonitrile.
  • Analyzing titration data to derive self-consistent HBA parameters (β) for each anion.

Main Results:

  • Determined self-consistent HBA parameters (β) for 15 anions, including halides, carboxylates, and sulfonates.
  • Demonstrated the transferability of anion HBA parameters across different solvents and HBD partners.
  • Identified carboxylates as exceptionally strong HBAs (β ≈ 15), significantly exceeding neutral organic HBAs.
  • Found hexafluorophosphate to be the weakest HBA among those studied, comparable to pyridine.
  • Confirmed negligible effects of ion pairing with counter-cations under specific conditions.

Conclusions:

  • Anion HBA parameters (β) are robust and transferable, allowing for predictable anion recognition.
  • The HBA strength of anions is not correlated with the pKa of their conjugate acids.
  • This work provides a valuable quantitative framework for designing systems with specific anion-binding capabilities.