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Electric current observed in aromatic compounds
An aromatic ring current is an effect observed in aromatic molecules such as benzene and naphthalene. If a magnetic field is directed perpendicular to
Aromatic_ring_current
Chemical property
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals
Aromaticity
Compound containing rings with delocalized pi electrons
properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as
Aromatic_compound
Cyclic chemical group (–C6H5)
shifts around 7.27 ppm. These chemical shifts are influenced by aromatic ring current and may change depending on substituents. Phenyl groups are usually
Phenyl_group
Hydrocarbon composed of multiple aromatic rings
A polycyclic aromatic hydrocarbon (PAH) is any member of a class of organic compounds that is composed of multiple fused aromatic rings. Most are produced
Polycyclic aromatic hydrocarbon
Polycyclic_aromatic_hydrocarbon
Electrons that are not associated with a single atom or covalent bond
several adjacent atoms. In the simple aromatic ring of benzene, the delocalization of six π electrons over the C6 ring is often graphically indicated by a
Delocalized_electron
Chemical compound
1H NMR of this compound exhibits hallmarks of a system with an aromatic ring current, with the 12H signal of exterior hydrogens at 9.25 ppm, while the
Cyclooctadecanonaene
Hydrocarbon compound (C6H6)
contained multiple double bonds or multiple rings, but in these years very little was known about aromatic chemistry, and so chemists were unable to adduce
Benzene
Molecule with a ring of bonded atoms
and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from
Cyclic_compound
Class of chemical compounds
anomaly is that the methyl protons are in line with the aromatic ring current of the benzene ring and are therefore severely shielded, an effect similar
In-Methylcyclophane
Property of conjugated systems with 4n delocalized electrons
contrast to the diamagnetic ring current present in aromatic compounds, antiaromatic compounds have a paramagnetic ring current, which can be observed by
Antiaromaticity
Boron compound
explosives such as CL-20. Carborazine (C 2H 2B 2N 2) is a six-membered aromatic ring with two carbon atoms, two nitrogen atoms, and two boron atoms in opposing
Borazine
Chemical compound
at low temperature by NMR. Its 1H NMR spectrum shows evidence of aromatic ring currents that result in an upfield shift for the interior hydrogens. In contrast
Cyclotetradecaheptaene
Organic compounds that contain sulfur
drawing away electrons to itself at the expense of the aromatic ring current. Yet as an aromatic substituent the thio group is less electron-releasing
Organosulfur_chemistry
Conjugated hydrocarbon ring molecules with at least one triple bond
internal protons of the dianion were negative and attributed to an aromatic ring current. The external proton next to the triple bond had a chemical shift
Annulyne
Computational methods for identifying aromatic ring systems
Aromaticity detection in cheminformatics refers to computational algorithms and models used to identify aromatic ring systems in molecular graphs. Unlike
Aromaticity_(cheminformatics)
Chemical compound
classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are
Indole
Chemical compound
is "moderately" aromatic as its ring current is 40% that of pyrrole, which is known to be aromatic. However, comparable ring current was calculated for
Arsole
Position of molecules attached to benzene rings
disubstituted aromatic ring (namely naphthalene). In 1870, the German chemist Viktor Meyer first applied Gräbe's nomenclature to benzene. The current nomenclature
Arene_substitution_pattern
Chemical compound
display aromaticity. It is not aromatic, however, because various types of ring strain destabilize an all-planar geometry. Although not aromatic itself
Cyclodecapentaene
Chemical compound
silicon's empty 3p orbital breaks the π ring, causing an upfield shift as the deshielding due to aromatic ring current is lost. Additionally there are significant
N-Heterocyclic_silylene
Aromatic compound (C4H4N2)
Pyrimidine (C4H4N2; /pɪˈrɪ.mɪˌdiːn, paɪˈrɪ.mɪˌdiːn/) is an aromatic, heterocyclic, organic compound similar to pyridine (C5H5N). One of the three diazines
Pyrimidine
Molecule with one or more rings composed of different elements
heteroatoms. In a 7-membered ring, the heteroatom must be able to provide an empty π-orbital (e.g. boron) for "normal" aromatic stabilization to be available;
Heterocyclic_compound
distortion of the hexagonal ring. 1H NMR signals for the ring protons are downfield, consistent with aromatic "ring current", and the ring readily undergoes electrophilic
Metallabenzene
Solid consisting of discrete molecules
two joined conjugated rings. The electronegativity of the atoms of this ring system and conjugation cause an aromatic ring current resulting in a quadrupole
Molecular_solid
Concept in theoretical chemistry
"super-ring" composed of a cyclic array of smaller aromatic rings. The concept is distinct from the common global aromaticity observed in single-ring macrocycles
Superaromaticity
Concept in chemistry
chemistry is an extension of the concept of homoaromaticity with two aromatic ring currents situated in a non-planar molecule and sharing the same electrons
Bicycloaromaticity
Chemical compound
ring, leading to considerable interest in the system in terms of its degree of lessened aromaticity. Questions of bond alternation and ring currents have
Biphenylene
Chemical compound
influence of the diamagnetic ring current which is characteristic of aromatic compounds. The peripheral protons around the ring are deshielded while the methylene
1,6-Methano(10)annulene
Chemical compound
degree of aromaticity greater than that of corresponding oxazoles. This aromaticity is evidenced by the 1H NMR chemical shift of the ring protons, which
Thiazole
Feature seen when light is gravitationally lensed by an object
Spilker announced their discovery of an Einstein ring of distant galaxy rich in organic molecules (aromatic hydrocarbons). In September 2023, a scientist
Einstein_ring
Chemical compound
Benzothiazole, or more specifically 1,3-benzothiazole, is an aromatic heterocyclic compound with the chemical formula C 7H 5NS. It is colorless, slightly
Benzothiazole
Chemical compound
protons resonating at −4.5 ppm relative to TMS, evidence of an aromatic diamagnetic ring current. In one study the 1,7-ditrans isomer is generated at low temperatures
Cyclododecahexaene
Heterocyclic aromatic organic compound
electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. In contrast to benzene, the
Pyridine
Effect of spatial atomic arrangement on properties of compounds
to substitution of isomers in the meta and para position. Electrophilic aromatic substitution of disubstituted benzene compounds causes steric effects which
Ortho_effect
Hydrocarbon compounds without aromatic rings
oil) are chemical compounds containing the element carbon that are not aromatic compounds. Aliphatic compounds can be saturated, where all C-C bonds are
Aliphatic_compound
Chemical compound
temperatures (> 2000 K). In particular, [N6]4- is aromatic, respecting Hückel's rule, while [N6]2- is anti-aromatic. The synthesis of the structural isomer, the
Hexazine
Subgroup of polymers
polymer chain and the ester groups are separated by an aromatic ring. A common form of cardo aromatic polyesters are ones in which bisphenol is incorporated
Cardo_polymer
Aromatic, boron-containing rings
properties of the borepin ring. Minimal substitution allowed scientists like Ashe to confirm the presence of aromaticity and ring currents within the borepin
Borepin
Organic chemical reaction
is the reaction of aromatic nitro compounds with potassium cyanide in aqueous ethanol to give the product of cine substitution (ring substitution resulting
Von_Richter_reaction
Chemical species structure notation
OC1CCCCC1O; choosing a different ring-break location produces a branched structure that requires parentheses to write. Aromatic rings such as benzene may be written
Simplified Molecular Input Line Entry System
Simplified_Molecular_Input_Line_Entry_System
Group of chemical compounds
consists of an aromatic moiety bridged by an aliphatic chain. The main difference between various derivatives of ansamycins is the aromatic moiety, which
Ansamycin
Notation used for specifying substructural patterns in chemical molecules
defines (aromatic carbon or aromatic nitrogen) with implicit hydrogen. The 'and' operator & has higher priority than , so [c,n&H] defines aromatic carbon
SMILES arbitrary target specification
SMILES_arbitrary_target_specification
Chemical compound
Rheingold, Arnold L. (1990-08-01). "Bora-aromatic systems. 12. Thermal generation and transformation of the borepin ring system: a paradigm of pericyclic processes"
Borole
Chemical activating melatonin receptors
aromatic ring. Various modulations showed promising activity, especially the naphthalene ring which is present in agomelatine (Figure 1). Other ring systems
Melatonin_receptor_agonist
Class of organic molecules
aromatic four membered ring system derived from squaric acid. Most squaraines are encumbered by nucleophilic attack of the central four membered ring
Squaraine_dye
Aromatic compounds containing Halogen atom(s) in place of Hydrogen
(also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halogen atom
Aryl_halide
Carcinogenic compound found in smoke and soot
polycyclic aromatic hydrocarbon found in coal tar with the formula C20H12. The compound is one of the benzopyrenes, formed by a benzene ring fused to pyrene
Benzo(a)pyrene
Type of organic reaction
Morgan–Walls reaction, the linker between the aromatic ring and the amide nitrogen is an ortho-substituted aromatic ring. This N-acyl 2-aminobiphenyl cyclizes
Bischler–Napieralski_reaction
Type of synthetic scents
(Soda Aromatic) Ambretone (Takasago) 15-Pentadecanolide Cyclopentadecanolide (Haarmann & Reimer) Exaltolide (Firmenich) Pentalide (Soda Aromatic)
Synthetic_musk
localization function analysis. NICS and ring current calculations have also been used to characterize the aromaticity in such systems by using magnetic criteria
Triboracyclopropenyl
Natural satellites of the planet Saturn
Titan and possibly Rhea, are currently in hydrostatic equilibrium. The remaining small moons, together with the rings, comprise only 0.04% of the orbiting
Moons_of_Saturn
Organic compound consisting entirely of hydrogen and carbon
have the formula CnH2n−2. Aromatic hydrocarbons, also known as arenes, which are hydrocarbons that have at least one aromatic ring. 10% of total nonmethane
Hydrocarbon
Chemical compound
(CH)3N2H. It is a heterocycle characterized as an azole with a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms, which are in ortho-substitution
Pyrazole
Chemical compound
commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It
Mesitylene
Chemical reaction
Next, a ring closing reaction occurs by the bond from the aromatic benzene ring attacking the partially positive carbonyl to form a five-member ring (5).
Martinet_dioxindole_synthesis
Chemical compound
dihydrobenzene ring is abstracted by an enzymatic base, thus causing the ring to become aromatic. The aromatic stabilization energy of the aromatic ring is what
Gabaculine
Unimolecular reactions
rearrangements of aromatic hydrocarbons are considered to be unimolecular reactions that directly involve the atoms of an aromatic ring structure and require
Thermal rearrangement of aromatic hydrocarbons
Thermal_rearrangement_of_aromatic_hydrocarbons
Chemical compound
exhibits Hückel aromaticity. Borirenes undergo ring-opening reactions with polar reagents and form Lewis adducts, due to the significant ring strain in its
Borirene
Mixture of fragrant substance
diffuse a pleasant and fragrant odor. They consist of artificial mixtures of aromatic chemicals and essential oils. The 1939 Nobel Laureate for Chemistry, Leopold
Perfume
Organic molecular structure
electrons, consistent with Huckel's rule for aromaticity. The magnetic field of the NMR could thus induce a ring current in the ion, responsible for the significant
Homoaromaticity
Hydrocarbon compounds composed of rings fused such that the molecule is nonplanar
contorted aromatics, or more precisely contorted polycyclic aromatic hydrocarbons, are polycyclic aromatic hydrocarbons (PAHs) in which the fused aromatic molecules
Contorted_aromatics
Chemical compound
(CH2) linked to each other to form a triangular ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane itself is
Cyclopropane
Compounds having a fully conjugated cyclic dione structure
nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. (Quinones are conjugated but not aromatic). Quinones are
Quinone
Chemical compound
acids. Trifluoroacetic acid does not protonate the molecule. 6-membered aromatic rings with one carbon replaced by another group:borabenzene, silabenzene,
Arsabenzene
Yellow chemical compound: building block of many dyes
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C 14H 8O 2. Several isomers exist but these
Anthraquinone
Organic bicyclic chemical
pair to the ring current, in accordance with Hückel's rule. As a result, 2,1,3-benzothiadiazole undergoes the standard chemistry of aromatic compounds,
2,1,3-Benzothiadiazole
water. An oxygen rebound mechanism can be assumed. GcoA positions the aromatic ring within the hydrophobic active site cavity where the heme is located
Cytochrome P450 aromatic O-demethylase
Cytochrome_P450_aromatic_O-demethylase
Chemical compound
(also referred as dioxin or p-dioxin) is a heterocyclic, organic, non-aromatic compound with the chemical formula C4H4O2.[page needed] It is colorless
1,4-Dioxin
Chemical compound
compound with the molecular formula C6HF5. The compound consists of a benzene ring substituted with five fluorine atoms. The substance is a colorless liquid
Pentafluorobenzene
Dietary supplement and medication
the aromatic nicotinamide ring is covalently bonded to adenine dinucleotide. The shared electrons of the other carbon atoms in the aromatic ring stabilize
Nicotinamide
Chemical compound
"Revealing Intuitively Assessable Chemical Bonding Patterns in Organic Aromatic Molecules via Adaptive Natural Density Partitioning". The Journal of Organic
Hexaphosphabenzene
Class of terpenes
tomatoes. Vetivazulene and guaiazulene are aromatic bicyclic sesquiterpenoids. With the addition of a third ring, the possible structures become increasingly
Sesquiterpene
Chemical compound
is a hypothetical chemical compound that consists of a six-membered aromatic ring containing five nitrogen atoms with the molecular formula CHN5. The
Pentazine
Chemical reaction
migration of halogen substituents to a different position on an aromatic or heteroaromatic ring, resulting in a net positional shift of the halogen from its
Halogen_dance_rearrangement
Substituted bicyclic heterocyclic compound derived from pteridine
to be important in solution. The pteridine ring system contains four nitrogen atoms, reducing its aromaticity to the point that it can be attacked by nucleophile
Pterin
Chemical compound
terephthalic acid (PTA) in the production of polyesters and other current polymers containing an aromatic moiety. Methods for the synthesis of the FDCA may be divided
2,5-Furandicarboxylic_acid
Chemical compound
polyesters. CBDO’s C4 ring is sufficiently rigid to prevent the two OH groups from forming cyclic structures. Unlike BPA, there is no current evidence of carcinogenic
2,2,4,4-Tetramethyl-1,3-cyclobutanediol
2,2,4,4-Tetramethyl-1,3-cyclobutanediol
Chemical compound
6-triamino-1,3,5-trinitrobenzene is an aromatic secondary explosive, based on the basic six-carbon benzene ring structure with three nitro functional groups
TATB
Chemical compound
4-ethoxy group attached to the benzyl ring has been cyclised round to the 3-position to form a 2,3-dihydrobenzofuran ring system. It was first reported in
Ethyleneoxynitazene
Antibiotic
of the cyclopropylpyrrolidine ring. The stereochemistry of the ring simply reflects the thermodynamics, since cis ring fusion is by far the most stable
Trovafloxacin
Chemical compound
a marked aromatic character. Protoporphyrin IX is essentially planar, except for the N-H bonds that are bent out of the plane of the rings, in opposite
Protoporphyrin_IX
Organic compound used in dyes
the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with
Acridine
Chemical compound
benzene rings. In dihydrophenanthrenes, part of the aromaticity is lost because two hydrogen atoms are added to adjacent carbon atoms of one ring. This
Dihydrophenanthrenes
Organic derivative of iodine
unfunctionalized arenes in the presence of a Brønsted or Lewis acid (an electrophilic aromatic substitution reaction). Diaryliodonium salts react with nucleophiles at
Hypervalent organoiodine compounds
Hypervalent_organoiodine_compounds
Chemical reaction
applied to other aromatic rings. As it generally begins with nucleophilic attack by the aromatic group, the electron density of the ring is an important
Formylation
Sixth planet from the Sun
2013, scientists at the IAA-CSIC reported the detection of polycyclic aromatic hydrocarbons in the upper atmosphere of Titan, a possible precursor for
Saturn
2-electron bond. Although the aromatic stabilization is the lowest for titanium of the Group 4 metals, the complex is aromatic. These computational results
Rosenthal's_reagent
Anti-nausea group of medications
carbonyl-containing linking moiety, aromatic/heteroaromatic ring, and a basic center. The carbonyl group is coplanar to the aromatic ring. 5-HT3 receptor antagonists
5-HT3_antagonist
Hydrocarbons are also commonly known as polycyclic aromatic hydrocarbons (PAHs) that are made up of aromatic rings. These pollutants are the byproducts of the
In_situ_bioremediation
Chemical reaction for synthesizing C–N bonds
(nucleophilic substitution, reductive amination, etc.) for the synthesis of aromatic C−N bonds, with most methods suffering from limited substrate scope and
Buchwald–Hartwig_amination
Chemical compound
transmission by 5HT2C and 5HT3 receptors: a role in the antidepressant response". Current Drug Targets. 7 (2): 165–75. doi:10.2174/138945006775515491. PMID 16475958
RS-102221
Overview of and topical guide to organic chemistry
constants Lewis acids and bases Chemoselectivity Molecular structure Aromaticity Chemical bonding Covalent bonding Lewis model Molecule shapes Bond angles
Outline_of_organic_chemistry
Molecules which bind other molecules
molecular tweezers bind aromatic guests. These molecular tweezers consist of a pair of anthracene arms held at a distance that allows aromatic guests to gain π–π
Molecular_tweezers
Chemical compound
has the molecular formula C16H14O6. Structurally, it consists of two aromatic rings connected by a central carbonyl group, characteristic of the benzophenone
Baishouwubenzophenone
Compounds that inhibit or block the activity of cannabinoid receptors
transmembrane-3-4-5-6 aromatic microdomain. The binding of rimonabant involves direct aromatic stacking interactions between its 2,4-dichlorophenyl ring and the Trp279/Phe200/Trp356
Cannabinoid receptor antagonist
Cannabinoid_receptor_antagonist
Development of a class of anti-migraine drugs
an antagonist. This is thought to be because the indole ring is unable to occupy the aromatic part of the binding site. Sumatriptan was the pioneer drug
Discovery and development of triptans
Discovery_and_development_of_triptans
Chemical compound
degradation to 1,2-dioxetanedione (note that many side-groups of the aromatic rings are not shown.): The reaction rate is pH dependent, and slightly alkaline
Bis(2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl)oxalate
Bis(2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl)oxalate
Organic compound (C6H5OH)
toward electrophilic aromatic substitution. The enhanced nucleophilicity is attributed to donation pi electron density from O into the ring. Many groups can
Phenol
coronene, and other aromatic molecules are involved. The typical columnar liquid-crystalline molecules have a pi-electron-rich aromatic core attached by
Columnar_phase
AROMATIC RING-CURRENT
AROMATIC RING-CURRENT
AROMATIC RING-CURRENT
AROMATIC RING-CURRENT
AROMATIC RING-CURRENT
AROMATIC RING-CURRENT
AROMATIC RING-CURRENT
AROMATIC RING-CURRENT
AROMATIC RING-CURRENT