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Related Concept Videos

Physical Properties of Amines01:26

Physical Properties of Amines

3.5K
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’...
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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...
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Molecular Shape and Polarity03:37

Molecular Shape and Polarity

62.1K
Dipole Moment of a Molecule
62.1K
Bond Polarity, Dipole Moment, and Percent Ionic Character02:48

Bond Polarity, Dipole Moment, and Percent Ionic Character

30.2K
Bond Polarity
30.2K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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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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Related Experiment Video

Updated: Sep 13, 2025

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Probing polarity structure-function relationships in amine-water mixtures.

Elizabeth Dach1, Elonne Pisacane2, Devon Campbell1

  • 1Department of Earth and Environmental Engineering, Columbia University, New York, NY, USA. n.y.yip@columbia.edu.

Chemical Communications (Cambridge, England)
|August 1, 2025
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Summary

This study reveals how amine chemical structure and polarity affect their miscibility with water. Hydrogen bonding and nanoscale ordering drive these interactions, influencing temperature-dependent water solubility.

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Area of Science:

  • Physical Chemistry
  • Chemical Thermodynamics
  • Solvent Science

Background:

  • Amine-water systems exhibit complex interactions influencing their solubility.
  • Understanding thermoresponsive hydrophilicity is crucial for various chemical applications.
  • The interplay between molecular structure and macroscopic properties requires detailed investigation.

Purpose of the Study:

  • To investigate the relationships between chemical structure, polarity, and miscibility in amine-water systems.
  • To elucidate the mechanisms governing the thermoresponsive hydrophilicity of amines.
  • To correlate molecular interactions with bulk solution behavior.

Main Methods:

  • Analysis of Kamlet-Taft parameters to quantify solvent properties.
  • Measurement of relative permittivity to probe molecular interactions.
  • Investigation of solvent-water systems with varying amine structures.

Main Results:

  • Identified key roles of hydrogen bonding and nanoscale ordering in amine-water interactions.
  • Demonstrated that molecular-level and mean-field effects influence miscibility.
  • Correlated specific chemical structures and polarity with thermoresponsive behavior.

Conclusions:

  • Hydrogen bonding and nanoscale ordering are fundamental to amine-water interactions.
  • These interactions dictate the temperature-dependent hydrophilicity (thermoresponsive behavior) of amines.
  • The findings provide a mechanistic understanding of miscibility in these systems.