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Related Concept Videos

Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

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When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...
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Structure of Benzene: Kekulé Model01:07

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In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
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Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

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According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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NMR Spectroscopy of Benzene Derivatives01:34

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Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Bioremediation00:46

Bioremediation

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Bioremediation is the use of prokaryotes, fungi, or plants to remove pollutants from the environment. This process has been used to remove harmful toxins in groundwater as a byproduct of agricultural run-off and also to clean up oil spills.
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A Data-Driven Perspective on Bioisostere Evaluation: Mapping the Benzene Bioisostere Landscape with BioSTAR.

Pol Hernández-Lladó1, Nicholas A Meanwell2,3,4,5, Angela J Russell1,6

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This study introduces a data-driven method to evaluate bioisosteric replacements in drug design. It quantitatively compares benzene bioisosteres, aiding medicinal chemists in selecting optimal alternatives for improved drug properties.

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Area of Science:

  • Medicinal Chemistry
  • Drug Design
  • Computational Chemistry

Background:

  • The selection of bioisosteres in drug design often relies on subjective experience.
  • An expanding array of novel bioisosteric scaffolds presents a challenge for medicinal chemists.
  • Objective criteria are needed for prioritizing bioisosteric replacements.

Purpose of the Study:

  • To present a data-driven approach for analyzing the bioisostere landscape.
  • To quantitatively compare benzene bioisostere replacements based on key drug properties.
  • To provide a framework (BioSTAR) for informed decision-making in bioisosteric selection.

Main Methods:

  • Utilized a data-mining workflow (BioSTAR) for bioisostere analysis.
  • Focused on benzene bioisosteres as a representative case study.
  • Quantitatively assessed the impact of bioisosteric replacements on bioactivity, solubility, and metabolic stability.

Main Results:

  • Demonstrated a quantitative comparison of benzene bioisosteres.
  • Highlighted successful applications of benzene bioisosteres in recent drug design.
  • Identified areas for future innovation in bioisostere design and application.

Conclusions:

  • A data-driven approach enhances the selection of bioisosteric replacements in drug design.
  • The BioSTAR workflow supports informed decision-making and inspires new bioisostere development.
  • Quantitative analysis of bioisosteres leads to improved drug properties and design strategies.