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Related Concept Videos

Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

5.9K
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...
5.9K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.3K
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...
3.3K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

4.7K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
4.7K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.6K
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...
3.6K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

2.8K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
2.8K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
3.9K

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Updated: Jul 3, 2025

Characterization of pH-Dependent Reversible Self-Assembly of Amyloid Beta 1-40-Coated Gold Colloids
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Robust binding between secondary amines and Au electrodes.

Weiyi Guo1, Timothy Quainoo2, Zhen-Fei Liu2

  • 1Department of Physics, City University of Hong Kong, Kowloon 999077, Hong Kong SAR, China. haixinli@cityu.edu.hk.

Chemical Communications (Cambridge, England)
|February 15, 2024
PubMed
Summary
This summary is machine-generated.

Secondary amines form robust single-molecule junctions with wax-coated gold electrodes. This binding is attributed to increased gold adatom formation, unlike with non-coated tips.

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Area of Science:

  • Molecular electronics
  • Surface science
  • Organic chemistry

Background:

  • Primary amines are common linkers in single-molecule junctions.
  • The effect of methyl substitution (forming secondary amines) on linker properties is not well understood.

Purpose of the Study:

  • Investigate the binding properties of secondary amines as linker groups.
  • Determine the influence of electrode coating on secondary amine junction formation.

Main Methods:

  • Fabrication of single-molecule junctions using secondary amines.
  • Utilized non-coated and wax-coated gold (Au) tips for electrode contact.
  • Analyzed junction stability and binding characteristics.

Main Results:

  • Robust binding of secondary amines to Au electrodes was absent with non-coated tips.
  • Successful and robust binding was achieved using wax-coated Au tips.
  • Proposed that frequent gold adatom formation on wax-coated tips catalyzes secondary amine binding.

Conclusions:

  • Secondary amines can function as effective linker groups in single-molecule junctions.
  • Electrode surface modification (wax coating) significantly impacts linker binding.
  • Gold adatom formation is a key factor in achieving robust secondary amine-gold electrode interactions.