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Physical Properties of Amines01:26

Physical Properties of Amines

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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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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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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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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Amines: Introduction01:07

Amines: Introduction

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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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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.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Tracking Aromatic Amines from Sources to Surface Waters.

Özge Edebali1, Simona Krupčíková1, Anna Goellner2

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Aromatic amines (AAs) are environmental contaminants found in industrial and domestic settings, posing risks to aquatic life. This review highlights their sources, environmental fate, and detection methods, emphasizing the need for further research.

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Area of Science:

  • Environmental Chemistry
  • Toxicology
  • Analytical Chemistry

Background:

  • Aromatic amines (AAs) are environmental contaminants with potential carcinogenic and mutagenic effects.
  • They contribute to the genotoxicity of industrial wastewater and exhibit acute toxicity to aquatic organisms.
  • Existing data on domestic sources, indoor occurrence, and environmental fate of AAs remain incomplete.

Purpose of the Study:

  • To review the environmental occurrence and fate of aromatic amines (AAs).
  • To identify key domestic sources of AAs, including cigarette smoke and grilled foods.
  • To evaluate the significance of nonindustrial sources on the overall environmental burden of AAs.

Main Methods:

  • Review of existing literature on aromatic amines.
  • Description of sampling techniques: copper-phthalocyanine trisulfonate materials, XAD resins in solid-phase extraction, and solid-phase microextraction.
  • Analysis of AA presence in domestic wastewater and indoor environments.

Main Results:

  • Aromatic amines are present in industrial wastewater, domestic environments (e.g., from cigarette smoke, grilled foods), and aquatic matrices.
  • Nonindustrial sources contribute to the overall environmental load of AAs.
  • Specific sampling techniques can provide insights into AA sources, transport, and fate.

Conclusions:

  • Gaps in understanding the sources, transport, and fate of AAs in domestic wastewater and indoor environments hinder effective prevention of adverse effects.
  • Further research on AAs and their environmental behavior is crucial for a comprehensive risk assessment.
  • Evaluating nonindustrial sources is important for managing the environmental impact of AAs.