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¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.4K
¹H NMR: Complex Splitting01:13

¹H NMR: Complex Splitting

1.7K
A proton M that is coupled to a proton X results in doublet signals for M. However, NMR-active nuclei can be simultaneously coupled to more than one nonequivalent nucleus. When M is coupled to a second proton A, such as in styrene oxide, each peak in the doublet is split into another doublet.
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied...
1.7K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.6K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.6K
UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

27.5K
UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the...
27.5K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.7K
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).
6.7K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

12.3K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...
12.3K

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Modeling Biologically Important NH···π Interactions Using peri-Disubstituted Naphthalenes.

Alexander F Pozharskii1, Olga V Dyablo1, Olga G Pogosova1

  • 1Department of Organic Chemistry, Southern Federal University, Zorge 7, 344090 Rostov-on-Don, Russian Federation.

The Journal of Organic Chemistry
|September 10, 2020
PubMed
Summary

Researchers studied NH···π interactions using naphthalene derivatives. They found these interactions are strongest with positively charged donors and electron-rich acceptors, with counterions significantly weakening the binding strength.

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A Technical Guide for Performing Spectroscopic Measurements on Metal-Organic Frameworks
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Area of Science:

  • Supramolecular Chemistry
  • Chemical Biology
  • Computational Chemistry

Background:

  • NH···π interactions are crucial for protein structure and molecular recognition.
  • Understanding these non-covalent forces is key to designing biomimetic systems.

Purpose of the Study:

  • To investigate the properties of NH···π interactions using model compounds.
  • To determine factors influencing the strength and geometry of NH···π bonds.
  • To explore the impact of counterions on NH···π interactions.

Main Methods:

  • Synthesis of 8-aryl and 8-pyrrolyl derivatives of 1-aminonaphthalene.
  • Spectroscopic and crystallographic analyses.
  • Quantum chemical calculations.

Main Results:

  • NH···π binding is enhanced by positively charged NH-donors and electron-rich π-donors (pyrrolyl, hydroxyphenyl).
  • Counterions (tetrafluoroborate) significantly weaken NH···π interactions through various mechanisms.
  • A record-strong NH···π interaction was observed in 8-(2,5-dimethylpyrrol-1-yl)-N,N-dimethylnaphthalene-1-ammonium tetrafluoroborate.

Conclusions:

  • Naphthalene derivatives serve as effective models for studying NH···π interactions.
  • Counterion effects play a critical role in modulating the strength of NH···π interactions in ionic systems.
  • The findings provide insights into the design of molecules for specific binding and structural stabilization.