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Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

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...

Preparation of Amines: Alkylation of Ammonia and Amines

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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.
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2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

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Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
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Free Energy Changes for Nonstandard States

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The free energy change for a process taking place with reactants and products present under nonstandard conditions (pressures other than 1 bar; concentrations other than 1 M) is related to the standard free energy change according to this equation:

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...

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Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia

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Putting ammonia into a chemically opened fullerene.

Keith E Whitener¹, Michael Frunzi, Sho-ichi Iwamatsu

¹Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.

Journal of the American Chemical Society

|September 27, 2008

Summary

Researchers encapsulated ammonia (NH3) within an open-cage fullerene. NMR and mass spectrometry confirmed NH3 inclusion, but it slowly escaped over six months, indicating limited stability.

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Ammonia Synthesis at Low Pressure

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Ammonia Synthesis at Low Pressure

Ammonia Synthesis at Low Pressure

Published on: August 23, 2017

Area of Science:

Supramolecular Chemistry
Nanomaterials Science
Physical Chemistry

Background:

Fullerenes are carbon-based nanomaterials with unique cage-like structures.
Open-cage fullerenes offer potential for molecular encapsulation.
Ammonia (NH3) is a fundamental chemical species with various applications.

Purpose of the Study:

To investigate the encapsulation of ammonia within a specific open-cage fullerene.
To characterize the properties and stability of the resulting fullerene-ammonia complex.
To determine the incorporation fraction and long-term retention of ammonia.

Main Methods:

Synthesis of an open-cage fullerene with a 20-membered ring orifice.
Encapsulation of ammonia (NH3) into the fullerene cage.
Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy and MALDI-TOF mass spectrometry.

Main Results:

Proton NMR confirmed endohedral NH3 presence with a characteristic resonance at delta H = -12.3 ppm.
MALDI-TOF mass spectrometry verified the intact fullerene and the fullerene-ammonia complex.
An incorporation fraction of 35-50% was determined, decreasing over six months, indicating ammonia escape.

Conclusions:

Ammonia can be successfully encapsulated within the studied open-cage fullerene.
The fullerene-ammonia complex exhibits measurable stability, but slow ammonia diffusion occurs over time.
This study provides insights into the host-guest chemistry of open-cage fullerenes and guest molecule dynamics.