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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.1K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.1K
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.
6.1K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.1K
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).
6.1K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

12.7K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
12.7K
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

7.2K
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
7.2K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.2K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.2K

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Updated: Jul 14, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Backbone Isomerization to Enhance Thermal Stability and Decrease Mechanical Sensitivities of 10 Nitro-Substituted

Jingwei Meng1, Teng Fei1,2, Jinxiong Cai1

  • 1Experimental Center of Advanced Materials, School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China.

ACS Applied Materials & Interfaces
|October 6, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed a new high-energy oxidizer, 3,3

Keywords:
backbone isomerizationbipyrazolehigh-energy density oxidizerthermostabilitytrinitromethyl

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Area of Science:

  • Energetic Materials Science
  • Organic Synthesis
  • Green Chemistry

Background:

  • Ammonium perchlorate (AP) is a widely used oxidizer but poses environmental concerns.
  • Developing novel, environmentally friendly, high-energy density oxidizers is crucial.
  • The trinitromethyl group is a promising substituent for designing advanced oxidizers.

Purpose of the Study:

  • To design and synthesize novel nitro group-substituted bipyrazoles as high-energy density oxidizers.
  • To investigate the effect of backbone isomerization on the properties of these compounds.
  • To develop safer and more stable alternatives to traditional oxidizers.

Main Methods:

  • Synthesis of 3,3',5,5'-tetranitro-1,1'-bis(trinitromethyl)-1H,1'H-4,4'-bipyrazole (3) via backbone isomerization.
  • Thermostability testing (Td) of synthesized compounds.
  • Mechanical sensitivity testing (impact and friction sensitivity) of synthesized compounds.

Main Results:

  • Compound 3 exhibited enhanced thermostability (Td = 156 °C) compared to its isomer 4 (Td = 125 °C).
  • Compound 3 showed improved mechanical sensitivity (IS = 13 J, FS = 240 N) over isomer 4 (IS = 9 J, FS = 215 N).
  • The synthesized oxidizer's properties are comparable to ammonium dinitramide (ADN).

Conclusions:

  • Backbone isomerization is an effective strategy for tuning the properties of nitro group-substituted bipyrazoles.
  • Compound 3 demonstrates promising potential as a high-energy density oxidizer with improved safety characteristics.
  • This research contributes to the development of greener and more efficient energetic materials.