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Related Concept Videos

Structure of Amines01:19

Structure of Amines

2.6K
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’...
2.6K
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

3.2K
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
3.2K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.2K
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).
6.2K
Mass Spectrometry of Amines01:19

Mass Spectrometry of Amines

4.3K
In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule: a molecule with an odd number of nitrogen atoms produces a parent ion with an odd molecular weight. The remaining fragments have an even mass.
Amines undergo fragmentation through α cleavage, producing nitrogen-containing cations—iminium ions—and alkyl radicals. Mass spectra of aromatic and cyclic aliphatic amines exhibit...
4.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

4.0K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
4.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
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.
2.9K

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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Ionization energies and ionization-induced structural changes in 2-phenylethylamine and its monohydrate.

Yair Yifrach1, Rami Rahimi1, Joshua H Baraban2

  • 1Department of Physics, Ben-Gurion University of the Negev, Beer-Sheva 8410501, Israel.

The Journal of Chemical Physics
|March 22, 2023
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Summary

This study investigated 2-phenylethylamine (PEA) and its monohydrate using advanced spectroscopy and quantum calculations. We revealed key interactions and structural changes upon ionization, crucial for understanding neurotransmitter behavior.

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Area of Science:

  • Physical Chemistry
  • Molecular Spectroscopy
  • Computational Chemistry

Background:

  • 2-phenylethylamine (PEA) is a biologically relevant neurotransmitter prototype.
  • Understanding interactions within PEA and its hydrate is crucial for molecular science.

Purpose of the Study:

  • To investigate the electronic structure and interactions of PEA and PEA-H2O.
  • To determine ionization energies and analyze geometric changes upon ionization.

Main Methods:

  • Resonance-enhanced two-photon ionization spectroscopy.
  • Photoionization and photodissociation efficiency curve measurements.
  • Quantum chemical calculations and electrostatic potential mapping.

Main Results:

  • Ionization energies for PEA and PEA-H2O were determined to be ~8.63 eV.
  • Charge separation was observed in neutral and ionic species.
  • Significant geometric changes, including hydrogen bond alterations, were identified upon ionization.

Conclusions:

  • The study provides detailed insights into the electronic and structural properties of PEA and its monohydrate.
  • Ionization significantly alters molecular geometry and hydrogen bonding in these neurotransmitter prototypes.