Community hub
Recent from talks
Contribute something to knowledge base
Content stats: 0 posts, 0 articles, 1 media, 0 notes
Members stats: 0 subscribers, 0 contributors, 0 moderators, 0 supporters
Subscribers
Supporters
Contributors
Moderators
Hub AI
Aromatic compound AI simulator
(@Aromatic compound_simulator)
Hub AI
Aromatic compound AI simulator
(@Aromatic compound_simulator)
Aromatic compound
Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's rule. Aromatic compounds have the following general properties:
Arenes are typically split into two categories - benzoids, that contain a benzene derivative and follow the benzene ring model, and non-benzoids that contain other aromatic cyclic derivatives. Aromatic compounds are commonly used in organic synthesis and are involved in many reaction types, following both additions and removals, as well as saturation and dearomatization.
Heteroarenes are aromatic compounds, where at least one methine or vinylene (-C= or -CH=CH-) group is replaced by a heteroatom: oxygen, nitrogen (azaarenes), or sulfur. Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called aliphatic. Approximately half of compounds known in 2000 are described as aromatic to some extent.
Aromatic compounds are pervasive in nature and industry. Key industrial aromatic hydrocarbons are benzene, toluene, xylene called BTX. Many biomolecules have phenyl groups including the so-called aromatic amino acids.
Benzene, C6H6, is the least complex aromatic hydrocarbon, and it was the first one defined as such. Its bonding nature was first recognized independently by Joseph Loschmidt and August Kekulé in the 19th century. Each carbon atom in the hexagonal cycle has four electrons to share. One electron forms a sigma bond with the hydrogen atom, and one is used in covalently bonding to each of the two neighboring carbons. This leaves six electrons, shared equally around the ring in delocalized pi molecular orbitals the size of the ring itself. This represents the equivalent nature of the six carbon-carbon bonds all of bond order 1.5. This equivalency can also explained by resonance forms. The electrons are visualized as floating above and below the ring, with the electromagnetic fields they generate acting to keep the ring flat.
The circle symbol for aromaticity was introduced by Sir Robert Robinson and his student James Armit in 1925 and popularized starting in 1959 by the Morrison & Boyd textbook on organic chemistry. The proper use of the symbol is debated: some publications use it to any cyclic π system, while others use it only for those π systems that obey Hückel's rule. Some argue that, in order to stay in line with Robinson's originally intended proposal, the use of the circle symbol should be limited to monocyclic 6 π-electron systems. In this way the circle symbol for a six-center six-electron bond can be compared to the Y symbol for a three-center two-electron bond.
Benzene derivatives have from one to six substituents attached to the central benzene core. Examples of benzene compounds with just one substituent are phenol, which carries a hydroxyl group, and toluene with a methyl group. When there is more than one substituent present on the ring, their spatial relationship becomes important for which the arene substitution patterns ortho, meta, and para are devised. When reacting to form more complex benzene derivatives, the substituents on a benzene ring can be described as either activated or deactivated, which are electron donating and electron withdrawing respectively. Activators are known as ortho-para directors, and deactivators are known as meta directors. Upon reacting, substituents will be added at the ortho, para or meta positions, depending on the directivity of the current substituents to make more complex benzene derivatives, often with several isomers. Electron flow leading to re-aromatization is key in ensuring the stability of such products.
For example, three isomers exist for cresol because the methyl group and the hydroxyl group (both ortho para directors) can be placed next to each other (ortho), one position removed from each other (meta), or two positions removed from each other (para). Given that both the methyl and hydroxyl group are ortho-para directors, the ortho and para isomers are typically favoured. Xylenol has two methyl groups in addition to the hydroxyl group, and, for this structure, 6 isomers exist.[citation needed]
Aromatic compound
Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's rule. Aromatic compounds have the following general properties:
Arenes are typically split into two categories - benzoids, that contain a benzene derivative and follow the benzene ring model, and non-benzoids that contain other aromatic cyclic derivatives. Aromatic compounds are commonly used in organic synthesis and are involved in many reaction types, following both additions and removals, as well as saturation and dearomatization.
Heteroarenes are aromatic compounds, where at least one methine or vinylene (-C= or -CH=CH-) group is replaced by a heteroatom: oxygen, nitrogen (azaarenes), or sulfur. Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called aliphatic. Approximately half of compounds known in 2000 are described as aromatic to some extent.
Aromatic compounds are pervasive in nature and industry. Key industrial aromatic hydrocarbons are benzene, toluene, xylene called BTX. Many biomolecules have phenyl groups including the so-called aromatic amino acids.
Benzene, C6H6, is the least complex aromatic hydrocarbon, and it was the first one defined as such. Its bonding nature was first recognized independently by Joseph Loschmidt and August Kekulé in the 19th century. Each carbon atom in the hexagonal cycle has four electrons to share. One electron forms a sigma bond with the hydrogen atom, and one is used in covalently bonding to each of the two neighboring carbons. This leaves six electrons, shared equally around the ring in delocalized pi molecular orbitals the size of the ring itself. This represents the equivalent nature of the six carbon-carbon bonds all of bond order 1.5. This equivalency can also explained by resonance forms. The electrons are visualized as floating above and below the ring, with the electromagnetic fields they generate acting to keep the ring flat.
The circle symbol for aromaticity was introduced by Sir Robert Robinson and his student James Armit in 1925 and popularized starting in 1959 by the Morrison & Boyd textbook on organic chemistry. The proper use of the symbol is debated: some publications use it to any cyclic π system, while others use it only for those π systems that obey Hückel's rule. Some argue that, in order to stay in line with Robinson's originally intended proposal, the use of the circle symbol should be limited to monocyclic 6 π-electron systems. In this way the circle symbol for a six-center six-electron bond can be compared to the Y symbol for a three-center two-electron bond.
Benzene derivatives have from one to six substituents attached to the central benzene core. Examples of benzene compounds with just one substituent are phenol, which carries a hydroxyl group, and toluene with a methyl group. When there is more than one substituent present on the ring, their spatial relationship becomes important for which the arene substitution patterns ortho, meta, and para are devised. When reacting to form more complex benzene derivatives, the substituents on a benzene ring can be described as either activated or deactivated, which are electron donating and electron withdrawing respectively. Activators are known as ortho-para directors, and deactivators are known as meta directors. Upon reacting, substituents will be added at the ortho, para or meta positions, depending on the directivity of the current substituents to make more complex benzene derivatives, often with several isomers. Electron flow leading to re-aromatization is key in ensuring the stability of such products.
For example, three isomers exist for cresol because the methyl group and the hydroxyl group (both ortho para directors) can be placed next to each other (ortho), one position removed from each other (meta), or two positions removed from each other (para). Given that both the methyl and hydroxyl group are ortho-para directors, the ortho and para isomers are typically favoured. Xylenol has two methyl groups in addition to the hydroxyl group, and, for this structure, 6 isomers exist.[citation needed]
Recent media
Recent media