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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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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?  
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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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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
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Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic Heteroaromatic Compounds.

Reid E Messersmith1, Sangeeta Yadav2, Maxime A Siegler1

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The Journal of Organic Chemistry
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PubMed
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Synthesized and characterized novel borepin polycyclic aromatics. These compounds exhibit significant aromaticity and unique electronic responses, offering insights into boron heterocycle chemistry.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Borepin-containing polycyclic aromatic compounds are of interest due to their unique electronic and magnetic properties.
  • Understanding the aromaticity of fused heterocyclic systems is crucial for designing new materials.

Purpose of the Study:

  • To synthesize and characterize two isomeric borepin-containing polycyclic aromatics.
  • To investigate the aromaticity and electronic properties of these novel compounds.
  • To compare their characteristics with existing literature data.

Main Methods:

  • Synthesis of borepin isomers via Z-olefins and borepin formation through stannocycle or dilithio intermediates.
  • Characterization using magnetic, crystallographic, and computational methods.
  • Quantum chemical calculations to assess local and global aromaticity.

Main Results:

  • Successful synthesis and characterization of two isomeric borepin polycyclic aromatics.
  • Demonstrated high local aromaticity within the borepin moieties due to fused benzo[b]thiophene units.
  • Observed unique electronic responses of each isomer to fluoride anions.
  • Experimental and computational data confirmed significant aromatic character in the borepin rings.

Conclusions:

  • The fused benzo[b]thiophene units enhance local aromaticity in borepin systems.
  • These compounds display distinct electronic behaviors, particularly towards fluoride ions.
  • Quantum chemical calculations provide a detailed understanding of aromaticity in complex boron heterocycles.