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General term in chemistry
Electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications: with regard to electron-transfer
Electron-rich
Reaction impacting chemical bonds
DA) reaction, the DAINV is a cycloaddition between an electron-rich dienophile and an electron-poor diene. During a DAINV reaction, three pi-bonds are
Inverse electron-demand Diels–Alder reaction
Inverse_electron-demand_Diels–Alder_reaction
Branch of photochemistry
Photoredox catalysis is a branch of photochemistry that uses single-electron transfer. Photoredox catalysts are generally drawn from three classes of materials:
Photoredox_catalysis
Description of a molecule's true bond structure as a combination of structures
structures. Electron delocalization stabilizes a molecule because the electrons are more evenly spread out over the molecule, decreasing electron-electron repulsion
Resonance_(chemistry)
Chemical bond by sharing of electron pairs
chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs
Covalent_bond
Attractive interactions between aromatic rings
fashion. Attractive π–π interactions exist between electron-rich benzene derivatives and electron-poor pyridinium rings. [2]Catanene was synthesized by
Stacking_(chemistry)
Organic compound (C6H5NH2); simplest aromatic amine
compounds. It is toxic to humans. Relative to benzene, aniline is "electron-rich". It thus participates more rapidly in electrophilic aromatic substitution
Aniline
Chemical compound
A ubiquinol is an electron-rich (reduced) form of coenzyme Q (ubiquinone). The term most often refers to ubiquinol-10, with a 10-unit tail most commonly
Ubiquinol
Chemical bond effect
where a region of negative charge interacts with a positive charge, the electron-rich π system can interact with a metal (cationic or neutral), an anion,
Pi-interaction
Chemical reaction
reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5): RC(=O)NR′R″ + HArZ +
Vilsmeier–Haack_reaction
Process in which a proton-rich nuclide absorbs an inner atomic electron
Electron capture (K-electron capture, also K-capture, or L-electron capture, L-capture) is a process in which the proton-rich nucleus of an electrically
Electron_capture
Dioxiranes are electrophilic oxidants that react more quickly with electron-rich than electron-poor double bonds; however, both classes of substrates can be
Oxidation_with_dioxiranes
Reaction of cyanide and alcohol to give imino ester salt
versa. The determining factor is typically how electron-rich or -poor the nitrile is. For example, an electron-poor nitrile is a good electrophile, readily
Pinner_reaction
Chemical compound
With two dimethylamino substituents, the ring is particularly electron rich. One-electron oxidation of TMPD gives the deep blue radical cation called Wurster's
Tetramethylphenylenediamine
Noncovalent molecular interaction
interaction is a noncovalent molecular interaction between the face of an electron-rich π system (e.g. benzene, ethylene, acetylene) and an adjacent cation
Cation–π_interaction
Chemical compound
to be a suitable reagent for introducing trifluoromethyl groups onto electron-rich aromatic compounds by Langlois; this reagent is also known as the Langlois
Sodium trifluoromethanesulfinate
Sodium_trifluoromethanesulfinate
Chemical compound
3-diene named after Samuel J. Danishefsky. Because the diene is very electron-rich it is a very reactive reagent in Diels-Alder reactions. This diene reacts
Danishefsky's_diene
Chemical catalyst
centre determines the rate of reaction. More electron rich imines reduce at faster rates than electron poor imines. The resulting iminium center undergoes
Frustrated_Lewis_pair
Aromatic compounds containing Halogen atom(s) in place of Hydrogen
the presence of Lewis acids. The decolouration of bromine water by electron-rich arenes is used in the bromine test. The oxychlorination of benzene has
Aryl_halide
Chemical compound
hypochlorite (bleach), and t-butylhypochlorite, and even chlorine. Electron-rich arenes are readily monochlorinated by NCS. Aniline and mesitylene are
N-Chlorosuccinimide
Chemical compound
4. Characterized borirenes to date are stabilized predominantly by electron-rich, strong σ- and π-donor substituents that raise the LUMO and lowers the
Borirene
Atom set which has replaced hydrogen atoms on a hydrocarbon's parent chain
and the mesomeric effect. Such effects are also described as electron-rich and electron withdrawing. Additional steric effects result from the volume
Substituent
Chemical theory
reactions taking place between electron rich alkenes and electron deficient (hetero)dienes, constituting the so-called inverse electron demand Diels–Alder reactions
Frontier molecular orbital theory
Frontier_molecular_orbital_theory
Chemical reaction for ortho-formylation of phenols
virtue of its two electron-withdrawing chlorine groups, the carbene (3) is highly electron deficient and is attracted to the electron rich phenoxide (5).
Reimer–Tiemann_reaction
Organic compound (CH3OC6H5) also named methoxybenzene
more electron-rich. The methoxy group strongly affects the pi cloud of the ring as a mesomeric electron donor, more so than as an inductive electron withdrawing
Anisole
Chemical reaction in which a nucleophile is affixed to the substrate
reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known
Nucleophilic_substitution
Chemical bond involving four bonding electrons; has one sigma plus one pi bond
two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in addition reactions
Double_bond
Chemical compound
Isoxazole is an electron-rich azole with an oxygen atom next to the nitrogen. It is also the class of compounds containing this ring. Isoxazolyl is the
Isoxazole
Chemical compound
reagent to test for indoles. The carbonyl group typically reacts with the electron rich 2-position of the indole but may also react at the C-3 or N-1 positions
Para-Dimethylaminobenzaldehyde
Para-Dimethylaminobenzaldehyde
Pericyclic chemical reaction
electrophile. The most nucleophilic atom is usually, but not always, the most electron-rich atom. In 1,3-dipolar cycloadditions, identity of the dipole-dipolarophile
1,3-Dipolar_cycloaddition
Benzene-1,2,3-triol
to phenols from sulfonic acids. Polyhydroxybenzenes are relatively electron-rich. One manifestation is the easy C-acetylation of pyrogallol. It was once
Pyrogallol
Chemicals that prevent body decomposition
charged molecule and other electron-rich species. As a result, the carbon in the formaldehyde molecule bonds with electron-rich nitrogen groups called amines
Embalming_chemicals
Type of electron microscope
electron microscope (SEM) is a type of electron microscope that produces images of a sample by scanning the surface with a focused beam of electrons.
Scanning_electron_microscope
Chemical reaction
site selective, providing products derived from reaction of the most electron-rich double bond in the substrate. It is common practice to perform this
Sharpless asymmetric dihydroxylation
Sharpless_asymmetric_dihydroxylation
Class of chemical compounds
Lindsay Smith, J. R.; McKeer, L. C.; Taylor, J. M. "4-Chlorination of Electron-Rich Benzenoid Compounds: 2,4-Dichloromethoxybenzene". Organic Syntheses
Chloramines
Chemical reaction
formation of an electrophile X+ that forms a covalent bond with an electron-rich, unsaturated C=C bond. The positive charge on X is transferred to the
Electrophilic_addition
Reaction in organic chemistry
1943) is a chemical reaction between a relatively electron-rich allyl group (the ene) and an electron-poor π bond (the enophile). The reaction is a pericyclic
Ene_reaction
Removal of proton(s) from a molecule in an acid-base reaction
may determine the product of a reaction. The conjugate base is more electron-rich than the molecule which can alter the reactivity of the molecule. For
Deprotonation
The Menke nitration is the nitration of electron rich aromatic compounds with cupric nitrate and acetic anhydride. The reaction introduces the nitro group
Menke_nitration
Cage-like allotrope of carbon
has been prepared where the metal center projects two electron-rich 'arms' that embrace the C 60 guest. Metal atoms or certain small molecules
Buckminsterfullerene
Chemical reaction
compound. The alkene must be electron rich which means that functional groups attached to the alkene must be able to donate electrons. Such alkenes are enol
Povarov_reaction
Chemical compound
H replaced by Br. The compound is a colorless oil. It is a standard electron-rich aryl halide substrate for cross coupling reactions. With magnesium it
Mesityl_bromide
Chemical compound
potency, with occasional exceptions. The phenyl region: It seems that an electron rich centre, such as phenyl, needs to be present. The beneficial effects
PDE3_inhibitor
Form of interaction between two atoms
additional parameter is the MC=N–C angle, which deviates from 180° in highly electron-rich systems. Other ligands have weak π-backbonding abilities, which creates
Pi_backbonding
hydrogen or alkyl, while R2 works best with aryl, but can also be alkyl. Electron-rich anilines, such as 4-methoxyaniline, tend to fail in this reaction. The
Gassman_indole_synthesis
Chemical compound
ketone is an organic compound with the formula of [(CH3)2NC6H4]2CO. This electron-rich derivative of benzophenone is an intermediate in the production of dyes
Michler's_ketone
Chemical reaction
are electron rich, enols behave as nucleophiles and react with electrophiles in much the same way that alkenes do. But because of resonance electron donation
Carbonyl α-substitution reaction
Carbonyl_α-substitution_reaction
Chemical reaction
Rieche formylation is a type of formylation reaction. The substrates are electron rich aromatic compounds, such as mesitylene or phenols, with dichloromethyl
Rieche_formylation
Chemical reaction
as an electrophile, the reaction is called electrophilic amination. Electron-rich organic substrates that may be used as nucleophiles for this process
Amination
Predictive model in organic chemistry
electron-deficient nucleophile, the σ* of the forming C-Nuc bond is lower in energy and better stabilized by attack antiperiplanar to electron-rich axial
Cieplak_effect
Chemical bond which does not involve the sharing of electrons
as an electrophile, or electron-seeking species, and forms a weak electrostatic interaction with a nucleophile, or electron-rich species. The nucleophilic
Non-covalent_interaction
Chemical species that accepts an electron pair from a nucleophile
interacts with electron-rich alkene molecule to form a π-complex 1. Forming of a three-membered bromonium ion The alkene is working as an electron donor and
Electrophile
Group of organonitrogen compounds
(the electron-rich ring that undergoes electrophilic substitution). In this process, the diazonium compound is attacked by, i.e., coupled to, electron-rich
Diazonium_compound
Organic redox reaction of aldehydes
reactions that do not produce great yields using only H2O2. Mostly electron rich aldehydes fall under this category. (See Limitation below) Also, solid-supported
Pinnick–Lindgren_oxidation
Cross-coupling reaction between boronic acid & an organohalide
under Suzuki reaction conditions. N-Heterocyclic carbenes are more electron rich and bulky than the phosphine ligand. Therefore, both the steric and
Suzuki_reaction
Class of chemical compounds
with lithiated phenylbisphosphine. In DuPhos the phosphorus atoms are electron-rich making the resulting metal complexes reactive. The phosphorus atoms
DuPhos
from the electron-rich subunit or moiety (electron donor) to an electron-poor moiety (electron acceptor), but disfavored (by several electron volts) in
Unimolecular_rectifier
Catalytic process
plasmon oscillations create an electron-rich region near the surface of the nanoparticle, which can be used to excite the electrons of nearby molecules. Similar
Plasmonic_catalysis
Chemical compound
electron-rich, and naturally undergoes aromatic substitution para to the sulfide. Oxidation to the sulfoxide or sulfone leaves the compound electron poor
Dibenzothiophene
reacts, for reactions involving "attack" of an electron-rich reacting species, the nucleophile, on an electron-poor reacting species, the electrophile. Specifically
Flippin–Lodge_angle
Chemical reaction
electrophile is possibly a species of the type R-C+=NHCl−. The arene must be electron-rich i.e. phenol or aniline type. A related reaction is the Gattermann reaction
Hoesch_reaction
Neutral heterocyclic compound
olefin (NHO) is a neutral heterocyclic compound with a highly polarized, electron-rich C=C olefin attached to a heterocycle made up of two nitrogen atoms.
N-Heterocyclic_olefins
Class of carbon compounds
orbital. Together, these orbitals give the central carbon a highly electron-rich character and explain its Lewis basic behavior. The first crystallographically
Carbodicarbenes
Chemical process for converting alkenes to aldehydes
increasingly on chelating ligands, especially diphosphites. Additionally, electron-rich the hydride complex are less proton-like. Thus, as a result, the electronic
Hydroformylation
Chemical reaction
generally higher yielding when an electron-rich diene is involved. Electron-rich fulvenes react well with electron-poor dienes, and vice versa. Yields
6+4_Cycloaddition
Class of organometallic compounds
metals with a d6 electron count, such as Mn(I) or Ru(II), a subsequent 1,2-H shift gives the vinylidene complex. For some electron-rich transition metals
Transition metal vinylidene complex
Transition_metal_vinylidene_complex
Obsolete concept in chemistry
the electrophilic sulfur radical the charge transfer is largest with electron-rich alkenes such as acrylonitrile but the resulting reduction in activation
Reactivity–selectivity principle
Reactivity–selectivity_principle
Chemical reaction which adds a nitro (–NO2) group onto a molecule
the attack by the electron-rich benzene ring: Alternative mechanisms have also been proposed, including one involving single electron transfer (SET). Selectivity
Nitration
Class of metallocene cations
the structure of a primary ferrocenylmethylium cation occurred via an electron rich nonamethylferrocenylmethylium cation with a bulky anion in 2000. Prior
Group 8 metallocenylmethylium cation
Group_8_metallocenylmethylium_cation
Chemical reaction in organic chemistry
plot for representative cases involving C–H cleavage in an electron-rich, neutral, or electron-poor (hetero)arene. eCMD has been proposed as a polarization-based
Concerted metalation deprotonation
Concerted_metalation_deprotonation
Organic compound of the form >C=C=O
carbodiimides, and electron-rich alkynes (the latter forming cyclobutenones). cis Alkenes react more easily than trans alkenes. Electron-withdrawing substituents
Ketene
Specific recurring patterns that are present in the modern periodic table
an electron-deficient species, called an electrophile, to accept electrons. Similarly, nucleophilicity is defined as the affinity of an electron-rich species
Periodic_trends
Chemical compound
compound is oxidizable in air but practically non-biodegradable. As an electron-rich aromatic, 2,4,6-tri-tert-butylphenol can also be easily oxidized electrochemically
2,4,6-Tri-tert-butylphenol
Chemical compound
substrate. Despite its high reactivity, DMDO displays good selectivity for electron-rich olefins. DMDO will also oxidize several other functional groups. For
Dimethyldioxirane
Chemical equilibrium between a relatively stable carbene compound and its dimer
compound and its dimer. The equilibrium was proposed to apply to certain electron-rich alkenes, such as tetraminoethylenes, which have been called "carbene
Wanzlick_equilibrium
with amines. It follows logically that carbon disulfide reacts with electron-rich complexes. The history of this area begins with the reaction of zero-valent
Transition metal complexes of carbon disulfide
Transition_metal_complexes_of_carbon_disulfide
Chemical compound
released and the carbazole is formed. Diphenylamine derivatives, being electron rich, are naturally oxidized to carbazoles when heated in air; a similar
Carbazole
Aromatic, heterocyclic compound
carboxylic acids. The 1,2,4-triazines can react with electron-rich dienophiles in an inverse electron demand Diels-Alder reaction. This forms a bicyclic
Triazine
nitration reaction in which a bromine is replaced by a nitro group on an electron-rich aryl compound such as a phenol or cresol. Typical reagents are nitrous
Zincke_nitration
Permanent bond dipole due to electron-rich or -poor groups in a molecule
effect in a molecule is a local change in the electron density due to electron-withdrawing or electron-donating groups elsewhere in the molecule, resulting
Inductive_effect
class of sandwich compounds consisting of an f-block metal and a set of electron-rich ligands such as the cyclopentadienyl anion. The first prepared and well-characterized
F-block_metallocene
Type of chemical bond in metals
conduction electrons (in the form of an electron cloud of delocalized electrons) and positively charged metal ions. Metal atoms lose their valence electrons to
Metallic_bonding
Chemical reaction in which halogen substituents are added to aromatic molecules
ions being more susceptible to electrophilic attack as they are more electron-rich. Chlorination of toluene with chlorine without catalyst requires a polar
Electrophilic_halogenation
American radiochemist
Sanford, Melanie. "Copper-mediated Late-Stage Radiofluorination of Electron-rich Arenes". Wright, Jay S.; Kaur, Tanpreet; Preshlock, Sean; Tanzey, Sean
Peter_J._H._Scott
Chemical compound
with appropriate electron acceptors. Generally, electron-deficient pi bonds undergo cyclization with TMMs more easily than electron-rich pi bonds. Usually
Trimethylenemethane
A molecular electron-reservoir complex is one of a class of redox-active systems which can store and transfer electrons stoichiometrically or catalytically
Iron_arene_complexes
Chemical compound
condensations. Deprotonation at the 7-position gives a particularly electron-rich ligand as manifested in the redox properties of ditungsten tetra(hpp)
Triazabicyclodecene
Molecule
method of α-bromination as it is high-yielding with few side-products. Electron-rich aromatic compounds, such as phenols, anilines, and various aromatic
N-Bromosuccinimide
Organic compound (CH2)4
reaction, irradiated carbonyls cyclize to a cyclobutanol. Ketenes attack electron-rich alkenes to give cyclobutanones. 1,4-Dihalobutanes convert to cyclobutanes
Cyclobutane
Chemical reaction used in organic synthesis
the oxidative addition requires an electron rich metal, hence favoring electron donating ligands. However, an electron deficient metal is more favorable
Stille_reaction
Chemical reaction
number of dienes have been employed in the reaction, although cyclic, electron-rich dienes such as those found in the cyclopentadiene and furan ring systems
(4+3)_cycloaddition
Model of chemical bonding in which three atoms share four electrons
The 3-center 4-electron (3c–4e) bond is a model used to explain bonding in certain hypervalent molecules such as tetratomic and hexatomic interhalogen
Three-center four-electron bond
Three-center_four-electron_bond
Extremely strong base
Xiulan; Sundermeyer, Jörg (2019). "Phosphazenyl Phosphines: The Most Electron-Rich Uncharged Phosphorus Brønsted and Lewis Bases". Angewandte Chemie International
Superbase
Chemical compound
Smith, J. R.; McKeer, L. C.; Taylor, J. M. (1993). "4-Chlorination of Electron-Rich Benzenoid Compounds: 2,4-Dichloromethoxybenzene". Organic Syntheses;
Morpholine
Covalent bond between two carbon atoms
Klaus; Simon, Arndt (1991). "Tetrakis(dimethylamino)ethene: An Extremely Electron-Rich Molecule with Unusual Structure both in the Crystal and in the Gas Phase"
Carbon–carbon_bond
Chemical compound
6-trinitrobenzoic acid. 1,3,5-Trinitrobenzene forms charge-transfer complexes with electron-rich arenes. Reduction of 1,3,5-trinitrobenzene gives 1,3,5-triaminobenzene
1,3,5-Trinitrobenzene
Chemical reaction which adds one or more halogen elements to a compound
kind of reaction typically works well for chlorine and bromine with electron-rich aromatic substrates. Often a Lewis acidic catalyst is used, such as
Halogenation
Chemical reaction
with electron-rich starting materials. Phenols are a common substrate, as they readily deprotonate to excellent phenoxide nucleophiles. Other electron-rich
Formylation
Chemical compound
have also been demonstrated: ROH + CH2=CHOAc → ROCH=CH2 + HOAc. As an electron-rich alkene, vinyl acetate undergoes a variety of additions. Diels-Alder
Vinyl_acetate
Radicals centered on boron atoms
normally slow single-step hydrogen atom abstraction (HAT) reaction from an electron rich C-H bond can be split into two steps where the radicals and substrates
Boryl_radicals
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