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Related Concept Videos

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

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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...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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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...
2.9K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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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 +...
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.9K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.2K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
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Understanding Stacking Interactions between an Aromatic Ring and Nucleobases in Aqueous Solution: Experimental and

Evgeny A Kataev1, Tatiana A Shumilova1, Benjamin Fiedler1

  • 1Institute of Chemistry, Faculty of Natural Sciences, Technische Universität Chemnitz , 09107 Chemnitz, Germany.

The Journal of Organic Chemistry
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This study quantifies stacking interactions between aromatic compounds and nucleobases in water. Guanine shows the strongest binding affinity, suggesting stacking interactions are key in molecular recognition.

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Area of Science:

  • Biophysical Chemistry
  • Molecular Recognition
  • Nucleic Acid Chemistry

Background:

  • Stacking interactions between aromatic compounds and nucleobases are vital for nucleotide and nucleic acid recognition.
  • A comprehensive understanding of the strength and selectivity of these interactions in aqueous solution remains challenging.

Purpose of the Study:

  • To experimentally determine stacking free energies between five nucleobases and anthracene.
  • To evaluate three different experimental methods for quantifying these interactions.
  • To compare experimental results with theoretical predictions using DFT calculations.

Main Methods:

  • Design and analysis of model complexes.
  • Thermodynamic double mutant cycles for experimental free energy determination.
  • Density Functional Theory (DFT) calculations for theoretical analysis.

Main Results:

  • Experimental stacking free energies were determined for guanine (G), thymine (T), uracil (U), cytosine (C), and adenine (A) with anthracene.
  • The binding preference order was G > T > U > C > A (kcal/mol).
  • DFT calculations showed a trend correlating with experimental findings.

Conclusions:

  • Stacking interactions are dominant over hydrophobic effects in aqueous solutions.
  • DFT calculations can accurately predict these stacking interactions.
  • This work provides crucial insights into the molecular recognition of nucleic acids.