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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 ...
Contributing structures of the carbonate ion. In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or forms, [1] also variously known as resonance structures or canonical structures) into a resonance hybrid (or hybrid structure) in valence bond theory.
The resonance stabilization of thiophene is 29 kcal/mol (121 kJ/mol) compared to 20 kcal/mol (84 kJ/mol) for the oxygen analogue furan. The reason for this difference is the higher electronegativity for oxygen drawing away electrons to itself at the expense of the aromatic ring current.
In chemistry, the mesomeric effect (or resonance effect) is a property of substituents or functional groups in a chemical compound. It is defined as the polarity produced in the molecule by the interaction of two pi bonds or between a pi bond and lone pair of electrons present on an adjacent atom. [ 1 ]
Two different resonance forms of benzene (top) combine to produce an average structure (bottom). In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected by the stabilization of conjugation alone.
Resonance structures of normal-demand dienes and dienophiles In general, the regioselectivity found for both normal and inverse electron-demand Diels–Alder reaction follows the ortho-para rule , so named, because the cyclohexene product bears substituents in positions that are analogous to the ortho and para positions of disubstituted arenes.
Thieno[3,2-b]thiophene. In organic chemistry, thienothiophene is any of several compounds consisting of two fused thiophene rings. They have the molecular formula C 6 H 4 S 2. Three constitutional isomers have been synthesized: thieno[3,2-b]thiophene, thieno[2,3-b]thiophene, and thieno[3,4-b]thiophene. The other isomer features S(IV) and is ...
As a consequence, thiophene exhibits few properties expected for a sulfide – thiophene is non-nucleophilic at sulfur and, in fact, is sweet-smelling. Upon hydrogenation , thiophene gives tetrahydrothiophene , C 4 H 8 S, which indeed does behave as a typical sulfide.