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Michael Faraday first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name bicarburet of hydrogen.
The cyclic nature of benzene was finally confirmed by the crystallographer Kathleen Lonsdale in 1929.
Ring formula Edit
The empirical formula for benzene was long known, but its highly polyunsaturated structure, with just one hydrogen atom for each carbon atom, was challenging to determine. Archibald Scott Couper in 1858 and Joseph Loschmidt in 1861 suggested possible structures that contained multiple double bonds or multiple rings, but too little evidence was then available to help chemists decide on any particular structure.
In 1865, the German chemist Friedrich August Kekulé published a paper suggesting that the structure contained a six-membered ring of carbon atoms with alternating single and double bonds. The evidence being that there always appeared to be only one isomer of any monoderivative of benzene, and that there always appeared to be exactly three isomers of every diderivative—now understood to correspond to the ortho, meta, and para patterns of arene substitution—to argue in support of his proposed structure. Kekulé's symmetrical ring could explain these curious facts, as well as benzene's 1:1 carbon-hydrogen ratio.
substituent patterns Edit
Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.
Ortho, meta, and para substitution Main arene substitution patterns. See also: Electrophilic aromatic substitution
In ortho-substitution, two substituents occupy positions next to each other, which may be numbered 1 and 2. In the diagram, these positions are marked R and ortho. In meta-substitution the substituents occupy positions 1 and 3 (corresponding to R and meta in the diagram). In para-substitution, the substituents occupy the opposite ends (positions 1 and 4, corresponding to R and para in the diagram). The toluidines serve as an example for these three types of substitution.
Ipso-substitution describes two substituents sharing the same ring position in an intermediate compound in an electrophilic aromatic substitution. Meso-substitution refers to the substituents occupying a benzylic position. It is observed in compounds such as calixarenes and acridines. Peri-substitution occurs in naphthalenes for substituents at the 1 and 8 positions.
Cine and tele substitution
In cine-substitution, the entering group takes up a position adjacent to that occupied by the leaving group. For example, cine-substitution is observed in aryne chemistry. Tele-substitution occurs when the new position is more than one atom away on the ring.
In the 19th and early-20th centuries, benzene was used as an after-shave lotion because of its pleasant smell. Prior to the 1920s, benzene was frequently used as an industrial solvent, especially for degreasing metal. As its toxicity became obvious, benzene was supplanted by other solvents, especially toluene (methyl benzene), which has similar physical properties but is not as carcinogenic.
others continued to use benzene as a component or significant contaminant until the late 1970s when leukemia deaths were found associated with Goodyear's Pliofilm production operations in Ohio.
X-ray diffraction shows that all of six carbon-carbon bonds in benzene are of the same length of 140 picometres (pm).
The C–C bond lengths are greater than a double bond (135 pm) but shorter than a single bond (147 pm). This intermediate distance is consistent with electron delocalization: the electrons for C–C bonding are distributed equally between each of the six carbon atoms. Benzene has 8 hydrogen atoms fewer than the corresponding parent alkane, hexane. The molecule is planar. One representation is that the structure exists as a superposition of so-called resonance structures, rather than either form individually. The delocalization of electrons is one explanation for the thermodynamic stability of benzene and related aromatic compounds.
The delocalized picture of benzene has been contested by Cooper, Gerratt and Raimondi in their article published in 1986 in the journal Nature. They showed that the electrons in benzene are almost certainly localized, and the aromatic properties of benzene originate from spin coupling rather than electron delocalization.
Public Health Edit
Benzene increases the risk of cancer and other illnesses. Benzene is a notorious cause of bone marrow failure. Substantial quantities of epidemiologic, clinical, and laboratory data link benzene to aplastic anemia, acute leukemia, and bone marrow abnormalities. The specific hematologic malignancies that benzene is associated with include: acute myeloid leukemia (AML), aplastic anemia, myleodysplastic syndrome (MDS), acute lymphoblastic leukemia (ALL), and chronic myeloid leukemia (CML).
The American Petroleum Institute (API) stated in 1948 that "it is generally considered that the only absolutely safe concentration for benzene is zero."[
(based on the wikipedia article)