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Related Concept Videos

Physical Properties of Amines01:26

Physical Properties of Amines

4.1K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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Structure of Amines01:19

Structure of Amines

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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’ carbon–carbon bond (154 pm). These aspects are...
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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.2K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
8.2K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.9K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

7.2K
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
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NMR Spectroscopy Of Amines01:19

NMR Spectroscopy Of 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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Synthesis of PolyN-isopropylacrylamide Janus Microhydrogels for Anisotropic Thermo-responsiveness and Organophilic/Hydrophilic Loading Capability
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Synthesis of PolyN-isopropylacrylamide Janus Microhydrogels for Anisotropic Thermo-responsiveness and Organophilic/Hydrophilic Loading Capability

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Molecular Microheterogeneity: Structure Formation in Amine-Water Mixtures.

Lena Friedrich1, Martina Požar2, Aurélien Perera3

  • 1Fakultät Physik/DELTA, Technische Universität Dortmund, D-44221 Dortmund, Germany.

Journal of the American Chemical Society
|January 15, 2026
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Summary

Aqueous alkylamines form stable microheterogeneous structures, mimicking soft matter. Their unique molecular self-assembly, driven by headgroups stabilizing water domains, explains unusual scattering and miscibility.

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Area of Science:

  • Physical Chemistry
  • Soft Matter Physics
  • Materials Science

Background:

  • Aqueous solutions of amphiphilic molecules often exhibit complex self-assembly.
  • Understanding molecular self-assembly is crucial for designing novel materials and processes.

Purpose of the Study:

  • To investigate the molecular self-assembly of aqueous alkylamine mixtures.
  • To explain the origin of intense structural prepeaks observed in X-ray scattering.
  • To elucidate the role of alkylamine headgroups in stabilizing microheterogeneity.

Main Methods:

  • X-ray scattering (temperature- and concentration-dependent).
  • Molecular dynamics simulations.
  • Analysis of structural prepeaks and diffraction patterns.

Main Results:

  • Discovery of exceptionally intense structural prepeaks in X-ray scattering, indicating nanoscale microheterogeneity.
  • Identification of bilayer-like arrangements of alkylamine headgroups stabilizing extended water domains.
  • Demonstration of stable microheterogeneity in macroscopically homogeneous solutions, unlike aqueous alcohols.
  • Molecular dynamics simulations confirmed headgroup saturation of water interfaces, preventing demixing.

Conclusions:

  • Aqueous alkylamines form a new class of molecular emulsions with bilayer-stabilized domains.
  • The observed scattering anomalies and miscibility are attributed to this unique molecular architecture.
  • Results suggest a need for a general theory on molecular-scale amphiphilicity mimicking soft-matter architectures.