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Thiophene is considered to be aromatic, although theoretical calculations suggest that the degree of aromaticity is less than that of benzene. The "electron pairs" on sulfur are significantly delocalized in the pi electron system. As a consequence of its aromaticity, thiophene does not exhibit the properties seen for conventional sulfides. For ...
[1] [2] Thieno[2,3-b]thiophene was the first member of the series to be isolated. It was obtained in very low yield upon heating citric acid, a source of a six-carbon linear chain, with P 4 S 10. [3] More efficient syntheses of this and the other two stable thienothiophenes involve cyclization reactions of substituted thiophenes. [1]
Because of their aromatic character, they are non-nucleophilic. The nonbonding electrons on sulfur are delocalized into the π-system. As a consequence, thiophene exhibits few properties expected for a sulfide – thiophene is non-nucleophilic at sulfur and, in fact, is sweet-smelling.
Thiophenol is an organosulfur compound with the formula C 6 H 5 SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol.The chemical structures of thiophenol and its derivatives are analogous to phenols, where the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring in phenol is replaced by a sulfur atom.
The extended Hückel method gives some degree of quantitative accuracy for organic molecules in general (not just planar systems) and was used to provide computational justification for the Woodward–Hoffmann rules. [5] To distinguish the original approach from Hoffmann's extension, the Hückel method is also known as the simple Hückel method ...
The 3,4-disubstituted thiophene called ethylenedioxythiophene (EDOT) is the precursor to the polymer PEDOT. Regiochemistry is not an issue in since this monomer is symmetrical. PEDOT is found in electrochromic displays, photovoltaics, electroluminescent displays, printed wiring, and sensors. [46]
The nitrogen (N)-containing aromatic rings can be separated into basic aromatic rings that are easily protonated, and form aromatic cations and salts (e.g., pyridinium), and non-basic aromatic rings. In the basic aromatic rings , the lone pair of electrons is not part of the aromatic system and extends in the plane of the ring.
Homoaromaticity, in organic chemistry, refers to a special case of aromaticity in which conjugation is interrupted by a single sp 3 hybridized carbon atom. Although this sp 3 center disrupts the continuous overlap of p-orbitals, traditionally thought to be a requirement for aromaticity, considerable thermodynamic stability and many of the spectroscopic, magnetic, and chemical properties ...