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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.5K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.5K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

7.5K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.5K
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
4.1K
Structure of Amines01:19

Structure of Amines

3.4K
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...
3.4K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.2K
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).
7.2K
Overview of Advanced Functional Groups02:22

Overview of Advanced Functional Groups

31.4K

Functional groups are groups of atoms with specific chemical properties that occur within organic molecules and are sometimes denoted as “R”. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of Advanced Functional Groups
The table below summarizes some of the major functional groups in organic chemistry.
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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

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Heptaphosphide cluster anions bearing group 14 element amide functionalities.

Gabriela Espinoza Quintero1, Isabelle Paterson-Taylor, Nicholas H Rees

  • 1Department of Chemistry and University of Oxford and Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK. jose.goicoechea@chem.ox.ac.uk.

Dalton Transactions (Cambridge, England : 2003)
|July 25, 2015
PubMed
Summary

Novel cluster anions containing germanium, tin, and lead were synthesized from the heptaphosphide dianion. The tin and lead compounds are stable, while the germanium analogue decomposes into a dimeric species.

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Area of Science:

  • Inorganic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • The heptaphosphide dianion, [HP7](2-), serves as a versatile precursor for synthesizing novel phosphorus-based cluster compounds.
  • Derivatization of main group element clusters offers pathways to new materials with unique electronic and structural properties.

Purpose of the Study:

  • To synthesize and characterize novel cluster anions by reacting [HP7](2-) with E[N(SiMe3)2]2 (E = Ge, Sn, Pb).
  • To investigate the stability and structural features of the resulting derivatized cluster anions.

Main Methods:

  • Multi-element solution-phase NMR spectroscopy (e.g., 31P NMR) for characterization.
  • Electrospray ionization mass spectrometry (ESI-MS) for molecular weight determination.
  • Single crystal X-ray diffraction for structural elucidation of key compounds.

Main Results:

  • Three novel cluster anions, [P7EN(SiMe3)2](2-) (E = Ge (1), Sn (2), Pb (3)), were successfully synthesized.
  • Compounds 1 and 2 were structurally characterized, revealing distinct coordination environments.
  • While the tin (2) and lead (3) analogues exhibit solution stability, the germanium (1) derivative readily decomposes to a dimeric species (4).

Conclusions:

  • The reaction of [HP7](2-) with E[N(SiMe3)2]2 provides access to a new family of P7-based cluster compounds.
  • The stability of these clusters is influenced by the identity of the main group element (E), with heavier elements promoting greater stability.
  • The observed decomposition pathway of the germanium cluster highlights the dynamic nature of phosphorus cluster chemistry.