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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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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...
2.8K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

10.0K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
10.0K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.6K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
3.6K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.7K
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...
2.7K
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

11.2K
Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
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N-Acenoacenes: Synthesis and Solid-State Properties.

Thomas Wiesner1, Marcel Pardon1, Steffen Maier1

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 10, 2022
PubMed
Summary
This summary is machine-generated.

Researchers synthesized four N-acenoacenes, analyzing their optoelectronic properties and solid-state packing. Two derivatives achieved high hole mobilities in organic thin-film transistors, showing promise for electronic applications.

Keywords:
azaacenesbisacenescrystal engineeringsemiconductorssolid-state packing

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Area of Science:

  • Organic chemistry
  • Materials science
  • Solid-state physics

Background:

  • N-acenoacenes are a class of organic molecules with potential optoelectronic applications.
  • Understanding their solid-state packing is crucial for optimizing device performance.

Purpose of the Study:

  • To synthesize and characterize novel N-acenoacene derivatives.
  • To investigate the relationship between molecular structure, solid-state packing, and optoelectronic properties.
  • To evaluate the performance of these materials in organic thin-film transistors (OTFTs).

Main Methods:

  • Synthesis of four N-acenoacene derivatives with varying substituents (TIPS-ethynyl, Boc, triflate).
  • Analysis of molecular structures and solid-state packing using X-ray crystallography.
  • Fabrication and characterization of OTFT devices using the synthesized materials.
  • Measurement of charge carrier mobility in the fabricated transistors.

Main Results:

  • Successful synthesis of four regioisomeric acridinoacridines.
  • Two TIPS-ethynyldiazaacenoacene derivatives exhibited promising optoelectronic properties.
  • Achieved saturation hole mobilities of up to 2.9×10⁻² cm²(Vs)⁻¹ in OTFTs.
  • Correlations between molecular packing and charge transport were observed.

Conclusions:

  • The synthesized N-acenoacenes demonstrate potential for use in organic electronics.
  • TIPS-ethynylated derivatives show particularly good performance in OTFTs.
  • Further research into structure-property relationships can lead to improved organic semiconductor materials.