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Class of chemical substituents
reactions. Electron-withdrawing groups exert an "inductive" or "electron-pulling" effect on covalent bonds. The strength of the electron-withdrawing group is
Electron-withdrawing_group
reaction. An electron withdrawing group (EWG) will have the opposite effect on the nucleophilicity of the ring. The EWG removes electron density from
Electrophilic aromatic directing groups
Electrophilic_aromatic_directing_groups
Chemical group (–OCH3)
methoxy substituent at the para position as an electron-donating group, but as an electron-withdrawing group if at the meta position. At the ortho position
Methoxy_group
Chemical reaction that removes a carboxyl group and releases carbon dioxide
carboxylic acids decarboxylate slowly, but carboxylic acids with an α electron-withdrawing group (e.g. β‑keto acids, β‑nitriles, α‑nitro acids, or arylcarboxylic
Decarboxylation
Variation on the Wittig chemical reaction
electron-withdrawing group (EWG) alpha to the phosphonate is necessary for the final elimination to occur. In the absence of an electron-withdrawing group
Horner–Wadsworth–Emmons reaction
Horner–Wadsworth–Emmons_reaction
Permanent bond dipole due to electron-rich or -poor groups in a molecule
in a molecule is a local change in the electron density due to electron-withdrawing or electron-donating groups elsewhere in the molecule, resulting in
Inductive_effect
Organic chemical reaction
cyanoacetic acid. Z−CHRR', for instance nitromethane. where Z is an electron withdrawing group. Z must be powerful enough to facilitate deprotonation to the
Knoevenagel_condensation
Reaction in organic chemistry
carbonyl compound (either an enone or an enal), or R" may be any electron withdrawing group. As originally defined by Arthur Michael, the reaction is the
Michael_addition_reaction
Chemical group (–CH=CH2)
(organomagnesiums) can attack with the vinyl end first. If next to an electron-withdrawing group, conjugate addition (Michael addition) can occur. Vinyl organometallics
Vinyl_group
General term in chemistry
acidity, electron-rich species are strong Lewis bases. Electron-withdrawing group Rosokha, Sergiy V.; Kochi, Jay K. (2008). "Fresh Look at Electron-Transfer
Electron-rich
Organic ring compound (C4H4NH)
of alkynes with isonitriles, where R2 is an electron-withdrawing group, and R1 is an alkane, aryl group, or ester. Examples of disubstituted alkynes
Pyrrole
effect of an electron-withdrawing substituent and an electron-donating substituent. The name originates as the electron-withdrawing group (EWG) is sometimes
Captodative_effect
Chemical reaction
sulfides. The substituent R next the amine methylene bridge is an electron-withdrawing group. The original 1928 publication by Thomas S. Stevens concerned
Stevens_rearrangement
Transmission of electronic effects through a system of conjugated chemical bonds
vinyl group and of an attached electron-withdrawing group (EWG; the π orbitals) are aligned and so can overlap and mix (i.e., are conjugated). Electron delocalization
Vinylogy
Chemical reaction of esters with halide anions
certain organic esters. This reaction applies to esters with a beta electron-withdrawing group (EWG). The reaction proceeds by nucleophilic dealkylation of the
Krapcho_decarboxylation
Chemical polarity due to interactions between pi bonds or lone pairs
the substituent is an electron-withdrawing group, and the effect is positive (+M) when the substituent is an electron donating group. Below are two examples
Mesomeric_effect
Class of hypervalent organoiodine compounds
organic side chains. Usually, R is an aryl group and R' is an electron-withdrawing group such as a sulfonyl group. The most commonly used iminoiodinane is
Iminoiodinane
Extremely strong acid
anions stabilized by three-dimensional aromaticity, as well as by electron-withdrawing group typically attached thereto. In superacids, the proton is shuttled
Superacid
Functional group, formula –CCl3
chlorine atom. Compounds with this group are a subclass of the organochlorines. Trichloromethyl is an electron withdrawing group owing to the electronegativity
Trichloromethyl_group
Organic reaction
nucleophilic aromatic substitutions the arene requires activation by an electron-withdrawing group preferably in the aromatic ortho position. In one modification
Smiles_rearrangement
Chemical reaction
α-amino-ketone (1) and a compound containing an electron-withdrawing group (e.g. an ester as shown) α to a carbonyl group (2). The mechanism requires zinc and acetic
Knorr_pyrrole_synthesis
Reaction impacting chemical bonds
This lowered energy results from the inclusion of either: A) electron withdrawing group, or B) electronegative heteroatoms. Aromatic compounds can also
Inverse electron-demand Diels–Alder reaction
Inverse_electron-demand_Diels–Alder_reaction
Free-energy relationship in organic chemistry
the reaction is consequently accelerated by electron withdrawing groups (EWG). The EWG withdraws electron density by resonance and effectively stabilizes
Hammett_equation
oxidation to either quinones. or iodonium ylides. Phenols with an electron- withdrawing group in the para position form the latter, while most other phenols
Phenol oxidation with hypervalent iodine reagents
Phenol_oxidation_with_hypervalent_iodine_reagents
Chemical reaction
(reverse) electron-demand Diels–Alder reaction, electron-withdrawing substituents on the diene lower the energy of its empty ψ3 orbital and electron-donating
Diels–Alder_reaction
Class of organic compounds
chemistry is a 1:1 reaction adduct between an arene carrying electron withdrawing groups and a nucleophile. These complexes are found as reactive intermediates
Meisenheimer_complex
Organic reaction
inventors who first published it in 1939. An electron-withdrawing group (EWG) on the alkene makes it electron deficient and although the reaction mechanism
Meerwein_arylation
Chemical reaction in organic chemistry
have been described: If the ylide carbon is substituted with an electron-withdrawing group (EWG), the reagent is referred to as a stabilized ylide. These
Johnson–Corey–Chaykovsky reaction
Johnson–Corey–Chaykovsky_reaction
Categorization of chemical reactions
alcohol. When R" is a good leaving group and electron withdrawing group such as a cyanide (CN) group, this group is eliminated and the corresponding
1,2-Wittig_rearrangement
Method for producing 2-aminopyridine derivatives
on sodium amide, (2) these electron-withdrawing groups can also form complexes with sodium amide, and (3) for single electron transfer pathway, altering
Chichibabin_reaction
Organic reaction
electrophilic substitution. Carbon nucleophiles carry an electron-withdrawing group and a leaving group: the nucleophile attacks the aromatic ring, and excess
Vicarious nucleophilic substitution
Vicarious_nucleophilic_substitution
Chemical reaction which attaches an electrophile to an aromatic ring
bearing the electron-withdrawing group (i.e., ortho or para attack) is less stable than the others. Therefore, these electron-withdrawing groups are meta
Electrophilic aromatic substitution
Electrophilic_aromatic_substitution
Influences on a molecule's properties not due to bonds or geometry
redistribution, an electron-withdrawing group (EWG) draws electrons away from a reaction center. When this center is an electron rich carbanion or an
Electronic_effect
Chemical compound
atom and carbonyl group (or any other electron-withdrawing group containing a multiple carbon-heteroatomic bond, e.g. amino group) can form part of a
Merocyanine
Breaking a molecular bond such that both fragments retain an electron
synergistic effect of both electron-withdrawing group and electron-donating group substituents. Electron-withdrawing groups often contain empty π* orbitals
Homolysis_(chemistry)
Dipolar compound
containing electron-withdrawing substituents will have a more partial negative charge, due to the ability of the nearby electron-withdrawing group to stabilize
Azomethine_ylide
Description of a molecule's true bond structure as a combination of structures
each C atom. With an electron-withdrawing group qi < 1 on the ortho and para C atoms and qi > 1 for an electron-releasing group. Weighting of the contributing
Resonance_(chemistry)
Organic compound (C6H5OH)
(2008). "Pentakis(trifluoromethyl)phenyl, a Sterically Crowded and Electron-withdrawing Group: Synthesis and Acidity of Pentakis(trifluoromethyl)benzene, -toluene
Phenol
Coupling reaction
carbon bond is formed. In one example, an oxime with a strongly electron withdrawing group reacts intramolecularly with the end of a diene to form a pyridine
Heck_reaction
Pericyclic chemical reaction
substituents (Ph v.s. COOMe) compete at withdrawing electrons from the alkene. The carboxyl is the better electron-withdrawing group, causing the β-carbon to be most
1,3-Dipolar_cycloaddition
Chemical reaction
alkyne substituents typically direct: larger groups prefer the C2 position, and electron-withdrawing groups prefer the C3 position. But the alkene itself
Pauson–Khand_reaction
Aromatic compounds containing Halogen atom(s) in place of Hydrogen
process. The method is often used for aryl chlorides also bearing electron-withdrawing groups. Illustrative is the synthesis of 2-fluoronitrobenzene from
Aryl_halide
pH indicator
bromocresol green. The presence of one moderate electron-withdrawing group (bromine atom) and two moderate donating groups (alkyl substituents) are responsible for
Bromothymol_blue
Chemical group (–OSO2CF3) or anion (charge –1)
trifluoromethyl group, which acts as a strong electron-withdrawing group using the sulfur atom as a bridge. Triflates have also been applied as ligands for group 11
Triflate
Chemical reaction
of the C=N double bond and gives the considerable yield with no electron withdrawing substituents. Similar mechanism also occurred in the reaction catalyzed
Ketimine_Mannich_reaction
Chemical reaction in organic chemistry
activated olefins such as those shown below where EWG refers to an electron withdrawing group such as cyano, keto, or ester as shown. The Wichterle reaction
Robinson_annulation
Chemical reaction
likely influence the route taken as when the methyl group of 1 is replaced by an electron-withdrawing group, the reaction instead proceeds through a diketone
Hantzsch_pyridine_synthesis
Organic compound (CH3OC6H5) also named methoxybenzene
ring as a mesomeric electron donor, more so than as an inductive electron withdrawing group despite the electronegativity of the oxygen. Stated more quantitatively
Anisole
Organic compound containing the functional group R–CH=O
form hydrates, R−CH(OH)2. These diols are stable when strong electron withdrawing groups are present, as in chloral hydrate. The mechanism of formation
Aldehyde
Chemical reaction used in organic chemistry
paradigm for "polarized" Nazarov cyclizations in which electron donating and electron withdrawing groups are used to improve the overall selectivity of the
Nazarov_cyclization
Chemical reaction mechanism
alkenes can be made to undergo conjugate substitution if they carry electron-withdrawing substituents, so normally nucleophilic aromatic rings also become
Nucleophilic aromatic substitution
Nucleophilic_aromatic_substitution
Removal of proton(s) from a molecule in an acid-base reaction
using resonance. Electron withdrawing groups (which can stabilize the molecule by increasing charge distribution) or electron donating groups (which destabilize
Deprotonation
Class of chemical reactions
the addition of electron-withdrawing fluorine substituents at the propargylic position. Fluorine is a good electron-withdrawing group in terms of synthetic
Bioorthogonal_chemistry
Preferential formation of one chiral isomer over another in a chemical reaction
and an electron-withdrawing group. For instance haloketones do not obey Cram's rule, and, in the example above, replacing the electron-withdrawing phenyl
Asymmetric_induction
Class of chemical compounds
commonly used. For stabilized Wittig reagents bearing conjugated electron-withdrawing groups, even relatively weak bases like aqueous sodium hydroxide or
Wittig_reagents
Chemical compound
of bromine on the benzene ring. NH2 is an electron donating group, and NO2 is an electron withdrawing group, which both direct bromination to the meta
NanoPutian
Organic redox reaction
reactants with electron-donating groups meta to the carbonyl group or electron-withdrawing groups ortho or para to the carbonyl group. Boric acid and
Dakin_oxidation
Chemical reaction
two electron withdrawing groups makes this reaction one of limited scope. The scope can be broadened to substrates containing one electron withdrawing group
Wolff_rearrangement
Copper-promoted cross-coupling reactions
amounts of copper. Aryl halides are required to be activated by electron-withdrawing groups. Traditional Ullmann style reactions used "activated" copper
Ullmann_condensation
Chemical reaction
largest LUMO coefficient in the dipolarophile (distant from the electron-withdrawing group) forms a bond with the nitrone oxygen, which possesses the largest
Nitrone-olefin (3+2) cycloaddition
Nitrone-olefin_(3+2)_cycloaddition
Chemical reaction involving repeated halogenation of an acetyl group (–COCH3)
reacts with hydroxide, with −CX3 being the leaving group stabilized by three electron-withdrawing groups. In the third step the −CX3 anion abstracts a proton
Haloform_reaction
Class of drugs used to treat malignant tumors
activity than normal cells, and the phosphoryl group, as an electron-withdrawing group, reduces the electron cloud density on the nitrogen atom in nitrogen
Antineoplastic
Preference of an electrocyclic reaction towards inward or outward rotation of substituents
selectivity can also be changed by the presence of electron donating and electron withdrawing groups. Other mechanisms by which torquoselectivity can operate
Torquoselectivity
Organic compound of the form >C(OH)O–
In organic chemistry, a hemiacetal is a functional group with the general formula R1R2C(OH)OR, where R1, R2 is a hydrogen atom or an organic substituent
Hemiacetal
Form of stereoisomerism in carbohydrates
The anomeric effect, which stabilizes the anomer that has an electron withdrawing group (typically an oxygen or nitrogen atom) in axial orientation on
Anomer
Organic reaction used to convert arenes to cyclohexadienes
mechanistically, with controversy lasting into the 1990s. The case with electron-withdrawing groups is obvious, because the Birch alkylation serves as a trap for
Birch_reduction
Chemical compound
Alternatively, cysteines in the positively charged environment or an electron-withdrawing group enable the thiosuccinimide ring to undergo self-hydrolysis. Another
Maleimide
Transition metal carbene complex
addition, and aldol reaction. The Cr(CO)5 moiety is a strong electron withdrawing group making the α-proton highly acidic. A methoxy chromium carbene
Fischer_carbene
Intermolecular forces between oppositely-charged sites on molecules
strongly electron withdrawing cyano group than when this atom is bound to a trifluoromethyl group, which is only moderately electron withdrawing. On the
Sigma_hole_interactions
Functional group made of a carbon-carbon-nitrogen heterocycle
3-dipolar cycloaddition. When the N-substituent is an electron-withdrawing group such as a tosyl group, the carbon-nitrogen bond breaks, forming another zwitterion
Aziridines
Organic molecule containing a neutral carbon with two unbound valence electrons
carbenes, in which the carbene is bonded to a metal that bears an electron-withdrawing group (usually a carbonyl). In such cases the carbenoid carbon is mildly
Carbene
Charged chemical group of the form >CO–
triacetoxyborohydride (Na+[HB(OAc)3]−) as a reagent. Bearing an electron-withdrawing group, sodium cyanoborohydride and sodium triacetoxyborohydride are
Oxocarbenium
Chemical compounds containing at least one xenon atom
element than fluorine or oxygen, particularly carbon. Electron-withdrawing groups, such as groups with fluorine substitution, are necessary to stabilize
Xenon_compounds
Chemical reaction which adds one or more halogen elements to a compound
procedures are available. When the aromatic substrate contains electron-withdrawing groups, halogenation does not proceed with the halogens. Potassium bromate
Halogenation
Class of enzymes
reduction of carbon-carbon double bonds (C=C) that are activated by electron withdrawing groups (EWG), like aldehydes, ketones and esters. The catalytic cycle
Ene-reductase
Chemical substance not composed of simpler ones
used as a general variable group.[citation needed] "E" is used in organic chemistry to denote an electron-withdrawing group or an electrophile;[citation
Chemical_element
Chemical reaction intermediate
cyclic hemiacetals and hemiacetals bearing electron withdrawing groups are stable. Electron-withdrawing groups attached to the carbonyl atom shift the equilibrium
Tetrahedral carbonyl addition compound
Tetrahedral_carbonyl_addition_compound
Measure of an acid's strength in solution
(2008). "Pentakis(trifluoromethyl)phenyl, a Sterically Crowded and Electron-withdrawing Group: Synthesis and Acidity of Pentakis(trifluoromethyl)benzene, -toluene
Acid_dissociation_constant
Chemical reaction
catalysts have been given interests as they could activate the electron-withdrawing group in an enantioselective manner. Chiral cationic oxazaborolidinium
Baylis–Hillman_reaction
Compound containing rings with delocalized pi electrons
described as either activated or deactivated, which are electron donating and electron withdrawing respectively. Activators are known as ortho-para directors
Aromatic_compound
Chemical reaction
mechanism shifts to a stepwise, Mannich-Michael pathway. Attaching an electron-withdrawing group to the imine nitrogen increases the rate. The exo isomer usually
Aza-Diels–Alder_reaction
Topics referred to by the same term
Baylis–Hillman reaction, a reaction of an aldehyde and an α,β-unsaturated electron-withdrawing group catalyzed by DABCO (1,4-diazabicyclo[2.2.2]octane) to give an
Baylis
Any part of a molecule with the chemical formula –CH2–
a methylene bridge located between two electron withdrawing groups (such as nitro, carbonyl or nitrile groups) are sometimes called active methylene compounds
Methylene_bridge
Reaction mechanism in organic chemistry
5-member cyclic transition state, yielding an alkene. The electron-withdrawing nitro group was found to increase both the rate of elimination and the
Ei_mechanism
Predictive model in organic chemistry
substituents on product distribution. By installing an electron-withdrawing substituent such as a methoxy group at the C2 position, the reduction of substituted
Cieplak_effect
Study of chemical compounds containing carbon-selenium bonds
at least one of the nitrogen or the selenium is attached to an electron-withdrawing group. Per Paulmier, "hexacoordinated selenium does not appear in organic
Organoselenium_chemistry
Chemical compound
case where an electron withdrawing group (EWG) is present in the substrate the highly electrophilic catalyst will oxidize the more electron-rich C–H bond
White–Chen_catalyst
Two phenyl rings linked by a N=N double bond
the 4 and 4' positions of the two azo rings with electron-donating and electron-withdrawing groups (that is, the two opposite ends of the aromatic system
Azobenzene
Type of paralyzing anesthetic including lepto- and pachycurares
inserting proper features into the molecule such as an appropriate electron withdrawing group then Hofmann elimination should occur at conditions in vivo. Atracurium
Neuromuscular-blocking_drug
value of sEDA the more sigma-electron donating is a substituent. The more negative sEDA, the more sigma-electron withdrawing is the substituent (see the
Sigma_electron_donor-acceptor
Chemical reaction
more difficult; however, adding an unsaturated ligand with an electron withdrawing group as a cocatalyst improved the yield in some systems. It is believed
Negishi_coupling
Measure of acidity for very strong acids
negative values. Hammett originally used a series of anilines with electron-withdrawing groups for the bases. Hammett also pointed out the equivalent form H
Hammett_acidity_function
Process of addition of silyl group(s) to compounds
substituents acting as electron withdrawing groups decrease the reaction rate. As bulker silyl groups are more likely to be electron withdrawing, it is easier
Silylation
Type of drugs
the majority of the strains. Furthermore, attachment of an electron withdrawing groups and heterocyclic rings such as thiophene and furan will increase the
Synthetic_drug
Chemical reaction
or delocalization of the electron lone pair through resonance. In general it can be claimed that an electron withdrawing group on the substrate, a strong
E1cB-elimination_reaction
Dye based on the rylene framework of naphthalene units
their strong electron affinities. In particular, OFETs using highly packed perylene diimide derivatives with electron withdrawing groups such were found
Rylene_dye
Chemical reaction
electron withdrawing groups (such as bromide) at the meta-position direct the rearrangement to the ortho-position (71% ortho product), while electron donating
Claisen_rearrangement
Chemical compound
be achieved by putting electron-withdrawing groups like amino, nitro, bromo or chloro at position 9 and 10 and hydroxyl group at position 10 or 11. But
Camptothecin
Chemical compound
bis(trifluoroacetyl) peroxide. In the CF3 radical the fluorine atom is an electron-withdrawing group via the inductive effect but also a weak pi donor through interaction
Trifluoromethylation
Organic chemistry reaction
carbocation intermediate, electron-withdrawing groups favor the SN2 reaction. Electron-donating groups favor leaving-group displacement and are more likely
SN2_reaction
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ELECTRON WITHDRAWING-GROUP
ELECTRON WITHDRAWING-GROUP
ELECTRON WITHDRAWING-GROUP
ELECTRON WITHDRAWING-GROUP