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Structures of Carboxylic Acid Derivatives01:28

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
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In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule; a molecule with an odd number of nitrogen atoms produces a molecular ion with an odd molecular weight. Amines undergo fragmentation through α cleavage, producing nitrogen-containing cations—iminium ions—and alkyl radicals. Mass spectra of aromatic and cyclic aliphatic amines exhibit strong molecular ion peaks, but acyclic...
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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
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In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is...
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Structural insights of mechanochemically amorphised MIL-125-NH2.

Emily V Shaw1, Celia Castillo-Blas1, Timothy Lambden1

  • 1Department of Materials Science & Metallurgy, University of Cambridge, 27 Charles Babbage Road, Cambridge, UK. cc2078@cam.ac.uk.

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Ball-milling destroys the structure of MIL-125-NH2 metal-organic framework, primarily through metal-linker bond breakage. This structural collapse impacts its photocatalytic properties and band gap.

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Area of Science:

  • Materials Science
  • Solid-State Chemistry
  • Nanotechnology

Background:

  • Metal-organic frameworks (MOFs) are porous materials with diverse applications.
  • MIL-125-NH2 is a MOF known for its stability and potential in catalysis.
  • Mechanical stress, like ball-milling, can alter MOF structures and properties.

Purpose of the Study:

  • To investigate the structural and chemical changes in MIL-125-NH2 upon prolonged ball-milling.
  • To understand the mechanism of structural disorder induced by mechanical stress.
  • To evaluate the impact of structural changes on the photocatalytic performance and electronic properties of MIL-125-NH2.

Main Methods:

  • Ball-milling of MIL-125-NH2 under varying durations.
  • Localised and bulk structural analyses (e.g., X-ray diffraction, spectroscopy).
  • Photocatalytic activity assessment.
  • UV-Vis reflectance spectroscopy for band gap determination.

Main Results:

  • Prolonged ball-milling leads to a complete loss of long-range structural order in MIL-125-NH2.
  • The secondary building units show partial retention of local bonding, indicating metal-linker bond breakage as the primary collapse mechanism.
  • Ball-milling significantly affects the photocatalytic performance and band gap of the material.

Conclusions:

  • Ball-milling is a destructive process for MIL-125-NH2, leading to amorphization.
  • The structural collapse mechanism involves the preferential breaking of metal-linker bonds.
  • The observed changes in electronic and photocatalytic properties are a direct consequence of the mechanical-induced structural disorder.