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Related Concept Videos

Physical Properties of Amines01:26

Physical Properties of Amines

4.4K
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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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...
11.6K
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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Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.7K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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N-Methylmelamines: Synthesis, Characterization, and Physical Properties.

Manuela List1, Helmut Puchinger1, Herbert Gabriel1

  • 1Institute for Chemical Technology of Organic Materials, Johannes Kepler University Linz , Altenbergerstrasse 69, 4040 Linz, Austria.

The Journal of Organic Chemistry
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N-methylmelamines offer a safer alternative to formaldehyde in polymer production. Their properties, like solubility and basicity, are tunable by adjusting methylamino and amino group numbers, impacting polymer characteristics.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • N-methylmelamines are crucial for developing modified melamine formaldehyde resins.
  • These resins offer reduced formaldehyde content, mitigating carcinogenicity concerns.
  • Understanding N-methylmelamine derivatives is key to controlling polymerization and material properties.

Purpose of the Study:

  • To synthesize and characterize all N-methylmelamine permutations.
  • To investigate the impact of N-methylation on melamine derivative properties.
  • To establish structure-property relationships for novel polymer building blocks.

Main Methods:

  • Synthesis of N-methylmelamine derivatives and 2,4,6-Tris(dimethylamino)-1,3,5-triazine.
  • Reaction monitoring using Gas Chromatography-Mass Spectrometry (GC/MS).
  • Characterization via NMR, IR, MS, elemental analysis, and X-ray diffraction; determination of physical properties (solubility, melting point, pKb).

Main Results:

  • Successful synthesis and high-purity isolation of N-methylmelamine derivatives.
  • Demonstrated correlation between the number of amino/methylamino groups and increased solubility and pKb values.
  • Observed increased melting points and decomposition with a higher number of amino groups due to hydrogen bonding.

Conclusions:

  • N-methylmelamine derivatives provide tunable properties for advanced polymer applications.
  • Structure-property relationships are established, guiding the selection of building blocks for specific resin characteristics.
  • This research facilitates the development of safer, high-performance melamine-based polymers.