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Related Concept Videos

NMR Spectroscopy Of Amines01:19

NMR Spectroscopy Of Amines

10.3K
In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is...
10.3K
Mass Spectrometry of Amines01:19

Mass Spectrometry of Amines

5.0K
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...
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Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

4.1K
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
4.1K
Structure of Amines01:19

Structure of Amines

2.9K
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’ carbon–carbon bond (154 pm). These aspects are...
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.0K
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...
3.0K
Amines: Introduction01:07

Amines: Introduction

5.1K
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Amidine Functionality As a Conformational Probe of Cyclic Peptides.

Sungjoon Huh1, Solomon D Appavoo1, Andrei K Yudin1

  • 1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.

Organic Letters
|November 18, 2020
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Summary

Amidine groups in macrocycles can act as hydrogen bond donors or acceptors, influencing molecular shape. This study shows amidines minimally alter conformation, aiding research into hydrogen bonding effects.

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Amidine groups are versatile functional groups capable of acting as both hydrogen bond donors and acceptors.
  • The role of hydrogen bonding in dictating macrocyclic conformation is crucial for molecular recognition and drug design.

Purpose of the Study:

  • To incorporate an amidine functionality into a specific macrocycle, cyclo(d-Ala-Pro-d-Phe-Pro-Gly), to investigate its impact on conformation.
  • To evaluate the effect of pH-dependent protonation of the amidine on the macrocyclic structure and hydrogen bonding network.

Main Methods:

  • Synthesis of an amidine-containing macrocycle.
  • Conformational analysis using techniques sensitive to hydrogen bonding and structural changes.
  • pH-dependent studies to probe the amidine's protonation states.

Main Results:

  • The unprotonated amidine-containing macrocycle adopted a conformation similar to its oxoamide analog.
  • Protonation of the amidine resulted in minimal changes to the overall macrocyclic conformation.
  • The amidine functionality was shown to disrupt existing hydrogen bonds with little steric penalty.

Conclusions:

  • Amidine incorporation offers a method to study hydrogen bonding effects in macrocycles due to its minimal steric impact.
  • The pH-switchable hydrogen bonding capability of amidines provides a tool for modulating macrocyclic conformation and interactions.