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Related Concept Videos

Structure of Amines01:19

Structure of Amines

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 illustrated in Figure...
Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

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 higher...
Weak Base Solutions03:21

Weak Base Solutions

Some compounds produce hydroxide ions when dissolved by chemically reacting with water molecules. In all cases, these compounds react only partially and so are classified as weak bases. These types of compounds are also abundant in nature and important commodities in various technologies. For example, global production of the weak base ammonia is typically well over 100 metric tons annually, being widely used as an agricultural fertilizer, a raw material for chemical synthesis of other...
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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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Related Experiment Video

Updated: Jun 5, 2026

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
12:06

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

Ammonium benzene-phospho-nate.

Zhen Lin, Xiu-Qing Lei, Sheng-Di Bai

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary
    This summary is machine-generated.

    Ammonium phenylphosphonate salt crystals feature a layered structure. Nitrogen and oxygen atoms form hydrogen bonds, creating layers sandwiched by stacked phenyl rings.

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    Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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    Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

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    Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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    Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

    Published on: February 15, 2016

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    Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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    Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
    06:35

    Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

    Published on: February 15, 2016

    Area of Science:

    • Crystallography
    • Solid-state chemistry
    • Materials science

    Background:

    • Understanding the crystal structures of salts is crucial for predicting their physical and chemical properties.
    • Phenylphosphonic acid derivatives are important in various chemical applications.
    • Ammonium salts offer unique hydrogen bonding capabilities.

    Purpose of the Study:

    • To elucidate the crystal structure of the ammonium salt of phenylphosphonic acid.
    • To investigate the intermolecular interactions governing the crystal packing.
    • To describe the self-assembly of the molecular components in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional crystal structure.
    • Analysis of hydrogen bonding networks and non-covalent interactions.
    • Examination of crystal packing through visualization of phenyl ring stacking.

    Main Results:

    • The crystal structure of ammonium phenylphosphonate was successfully determined.
    • A distinct layered motif was observed, formed by hydrogen bonding between ammonium cations and phosphonate anions.
    • Phenyl rings of the phosphonate groups were found to be stacked parallel to the hydrogen-bonded layers, effectively sandwiching them.

    Conclusions:

    • The crystal structure reveals a well-defined layered arrangement driven by hydrogen bonding.
    • The phenyl ring stacking plays a significant role in stabilizing the overall crystal architecture.
    • This structural insight contributes to the understanding of organic-inorganic hybrid materials and their assembly.