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Chemical species that donates an electron pair
can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. Nucleophilic describes the affinity of a nucleophile to bond with
Nucleophile
Reaction in organic chemistry
addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce
Michael_addition_reaction
Organic chemistry reaction
mechanism that is common in organic chemistry. In the SN2 reaction, a strong nucleophile forms a new bond to an sp3-hybridised carbon atom via a backside attack
SN2_reaction
Chemical species that accepts an electron pair from a nucleophile
chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons
Electrophile
Substitution reaction with a carbocation intermediate
and zero-order dependence on the nucleophile. This relationship holds for situations where the amount of nucleophile is much greater than that of the
SN1_reaction
supports the stereochemical assignment). An Ambident nucleophile refers to an anionic nucleophile that exhibits resonance delocalization of its negative
Ambident_(chemistry)
Chemical reaction
nucleophile displaces it. A common side-product is produced when the azodicarboxylate displaces the leaving group instead of the desired nucleophile.
Mitsunobu_reaction
Chemical compound (OH–)
usually minor constituent of water. It functions as a base, ligand, nucleophile, and catalyst. The hydroxide ion forms salts, some of which dissociate
Hydroxide
Substitution or elimination reaction where the nucleophile is a solvent
type of nucleophilic substitution (SN1/SN2) or elimination where the nucleophile is a solvent molecule. Characteristic of SN1 reactions, solvolysis of
Solvolysis
Chemical reaction in which a nucleophile is affixed to the substrate
chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule
Nucleophilic_substitution
Process that results in the interconversion of chemical species
pair from the nucleophile attacks the substrate forming a new bond, while the leaving group departs with an electron pair. The nucleophile may be electrically
Chemical_reaction
Set of three coordinated amino acids
amidases, esterases, acylases, lipases and β-lactamases). An acid-base-nucleophile triad is a common motif for generating a nucleophilic residue for covalent
Catalytic_triad
Protein structural motif
In molecular biology, the N-terminal nucleophile (Ntn)-hydrolases are a structural superfamily of evolutionarily related enzymes that have diverged beyond
N-terminal nucleophile hydrolases
N-terminal_nucleophile_hydrolases
Type of proteins
G proteins, also known as guanine nucleotide-binding proteins, are a family of proteins that act as molecular switches inside cells, and are involved in
G_protein
Palladium-catalysed substitution reaction
forming the π-allyl complex. This allyl complex can then be attacked by a nucleophile, resulting in the substituted product. This work was first pioneered
Tsuji–Trost_reaction
Chemical reaction mechanism
(SNAr) is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring
Nucleophilic aromatic substitution
Nucleophilic_aromatic_substitution
Chemical reaction involving organic compounds
an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H+ ion. The outcome of the reaction depends on reaction
Prins_reaction
reactions involving "attack" of an electron-rich reacting species, the nucleophile, on an electron-poor reacting species, the electrophile. Specifically
Flippin–Lodge_angle
Cleavage of chemical bonds by the addition of water
broadly for substitution and elimination reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of biomolecules where a water
Hydrolysis
Chemical group (R–C=O)
types of acyl derivatives. Acid halides are the most reactive towards nucleophiles, followed by anhydrides, esters, and amides. Carboxylate ions are essentially
Acyl_group
Chemical reaction involving the addition of a nucleophile to an electrophile
chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions
Nucleophilic_addition
Protein family
The PA clan (Proteases of mixed nucleophile, superfamily A) is the largest group of proteases with common ancestry as identified by structural homology
PA_clan_of_proteases
Angle in physical organic chemistry
fully define the geometry of "attack" (approach via collision) of a nucleophile on a trigonal unsaturated center in a molecule, originally the carbonyl
Bürgi–Dunitz_angle
Enzyme that cleaves other proteins into smaller peptides
to make a nucleophile is by a catalytic triad, where a histidine residue is used to activate serine, cysteine, or threonine as a nucleophile. This is not
Protease
Technique to describe progression of organic chemistry reaction mechanisms
a pictorial understanding of the source of electrons in a reaction (nucleophiles), sites to which they are attracted (electrophiles), and atoms or groups
Arrow_pushing
Independent evolution of similar features
amino acid functional groups (alcohol or thiol) as a nucleophile. To activate that nucleophile, they orient an acidic and a basic residue in a catalytic
Convergent_evolution
Effect in chemistry
reaction of the ester p-nitrophenyl acetate with a range of nucleophiles. Regular nucleophiles such as the fluoride anion, aniline, pyridine, ethylene diamine
Alpha_effect
Organic reaction
substitution is a special type of nucleophilic aromatic substitution in which a nucleophile replaces a hydrogen atom on the aromatic ring and not leaving groups
Vicarious nucleophilic substitution
Vicarious_nucleophilic_substitution
Monoamide of a phosphite diester
reactivity towards nucleophiles catalyzed by weak acids e.c., triethylammonium chloride or 1H-tetrazole. In these reactions, the incoming nucleophile replaces the
Phosphoramidite
Class of organic compounds
reaction adduct between an arene carrying electron withdrawing groups and a nucleophile. These complexes are found as reactive intermediates in nucleophilic
Meisenheimer_complex
Organic reaction
the incoming nucleophile is sufficiently strong that the arene does not require this additional activation, for example when the nucleophile is an organolithium
Smiles_rearrangement
Rule in organic chemistry
addition of nucleophiles to cyclohexene derivatives. Cyclohexene derivatives, such as imines, epoxides, and halonium ions, react with nucleophiles in a stereoselective
Fürst-Plattner_Rule
Sterically hindered organic base
a sterically hindered organic base that is a poor nucleophile. Normal bases are also nucleophiles, but often chemists seek the proton-removing ability
Non-nucleophilic_base
Chemical reaction mechanism
inside-out in a gale. In the Walden inversion, the backside attack by the nucleophile in an SN2 reaction gives rise to a product whose configuration is opposite
Walden_inversion
Compound derived from an acid
Esters react with nucleophiles at the carbonyl carbon. The carbonyl is weakly electrophilic but is attacked by strong nucleophiles (amines, alkoxides
Ester
Organic compound containing the functional group R–CH=O
From the biological perspective, the key reactions involve addition of nucleophiles to the formyl carbon in the formation of imines (oxidative deamination)
Aldehyde
Chemical reaction
Petasis reaction, the vinyl group of the organoboronic acid serves as the nucleophile. In comparison to other methods of generating allyl amines, the Petasis
Petasis_reaction
Organometallic compounds used in organic synthesis
covalent bond. The carbon atom has negative excess charge and acts as a nucleophile. Grignard reagents are rarely isolated as solids. Instead, they are normally
Grignard_reagent
Chemical reaction
alcohols as nucleophile typically generate ketals, where as the palladium-catalyzed oxidations of olefins with carboxylic acids as nucleophile generates
Wacker_process
Preferential formation of one chiral isomer over another in a chemical reaction
interactions involve those around R and the nucleophile but not the carbonyl oxygen atom. Attack of the nucleophile occurs according to the Dunitz angle (107
Asymmetric_induction
compound is replaced by a nucleophile through an intermediary free radical species: The substituent X is a halide and nucleophiles can be sodium amide, an
Radical-nucleophilic aromatic substitution
Radical-nucleophilic_aromatic_substitution
Chemical compound
Silicon tetrachloride or tetrachlorosilane is the inorganic compound with the formula SiCl4. It is a colorless volatile liquid that fumes in air. It is
Silicon_tetrachloride
Chemical reaction
rather than a ketone or aldehyde. This occurs even if the equivalents of nucleophile are closely controlled. The Weinreb–Nahm amide has since been adopted
Weinreb_ketone_synthesis
Class of chemical compounds
analogs of enols. Enamines are both good nucleophiles and good bases. Their behavior as carbon-based nucleophiles is explained with reference to the following
Enamine
Chemical reaction in which one functional group in a compound is replaced by another
nucleophilic substitution is a fundamental class of reactions in which a nucleophile selectively bonds with or attacks the positive or partially positive
Substitution_reaction
Catalysis of chemical reactions by enzymes
needed] Often general acid or base catalysis is employed to activate nucleophile and/or electrophile groups, or to stabilize leaving groups. Many amino
Enzyme_catalysis
Method for preparing ethers
reaction mechanism there is a backside attack of an electrophile by a nucleophile and it occurs in a concerted mechanism (happens all at once). In order
Williamson_ether_synthesis
Organic reaction
addition. A nucleophile reacts with a α,β-unsaturated carbonyl compound in the β position. The negative charge carried by the nucleophile is now delocalized
Nucleophilic conjugate addition
Nucleophilic_conjugate_addition
Chemical bond theory
named for the American physical chemist Gilbert N. Lewis. The terms nucleophile and electrophile are sometimes interchangeable with Lewis base and Lewis
Lewis_acids_and_bases
Ion
Imidazolate (C3H3N− 2) is the conjugate base of imidazole. It is a nucleophile and a strong base. The free anion has C2v symmetry. Imidazole has a pKa
Imidazolate
Predictive model in organic chemistry
chemistry, the Cieplak effect is a predictive model to rationalize why nucleophiles preferentially add to one face of a carbonyl over another. Proposed by
Cieplak_effect
Active region of an enzyme
catalysis: This process involves the donation of electrons from the enzyme's nucleophile to a substrate to form a covalent bond between them during the transition
Active_site
Proteinogenic amino acid
disulfide bonds, and often participates in enzymatic reactions as a nucleophile. Cysteine is chiral, but both D and L-cysteine are found in nature. L‑Cysteine
Cysteine
Chemical compound
Thiazyl fluoride is a compound with the chemical formula NSF. It is a colourless, pungent gas at room temperature and condenses to a pale yellow liquid
Thiazyl_fluoride
Chemical compound
attacking the chloride hydrogen, which forms a chloride nucleophile. In the second step, the nucleophile attacks the carbocation generated in the first step
2-Chlorobutane
Chemical reaction
species. This electrophilic intermediate may be attacked by a variety of nucleophiles or undergo rearrangement or elimination. Hypervalent iodine(III) compounds
Carbonyl oxidation with hypervalent iodine reagents
Carbonyl_oxidation_with_hypervalent_iodine_reagents
Group of chemical compounds derived from alkanes containing one or more halogens
triphenylphosphine oxide. In the Mitsunobu reaction, the reagents are any nucleophile, triphenylphosphine, and a diazodicarboxylate; the coproducts are triphenylphosphine
Haloalkane
Type of organic chemical reaction
entropy) the base is a poor nucleophile. Bases with steric bulk, (such as in potassium tert-butoxide), are often poor nucleophiles. For example, when a 3°
Elimination_reaction
Covalent bond joining a sugar molecule to another group
purity. It was suggested by Joshi et al. (2001) that lithium acts as the nucleophile that attacks the carbon at the 5-position and through a transition state
Glycosidic_bond
Chemical reaction that joins diazonium (R–N≡N) to an aromatic compound
(usually from an arene, which is called coupling agent), serves as a nucleophile. Classical coupling agents are phenols and naphthols. Usually the diazonium
Azo_coupling
Chemical compound
is a good electrophile, and the sulfimide S=N bond can be attacked by nucleophiles, such as alkoxides, enolates, and amide ions. The nitrogen atom in the
N-tert-Butylbenzenesulfinimidoyl chloride
N-tert-Butylbenzenesulfinimidoyl_chloride
British chemist (1893–1970)
responsible for the introduction into mainstream chemistry of concepts such as nucleophile, electrophile, inductive and resonance effects, and such descriptors
Christopher_Kelk_Ingold
Chemical reaction
α-substituted carboxylic acids from trichloromethylcarbinols and corresponding nucleophiles in the presence of sodium hydroxide. The reaction involves nucleophilic
Jocic_reaction
Protecting group used in organic synthesis
be the tendency of the t-butyl cation intermediate to alkylate other nucleophiles; scavengers such as anisole or thioanisole may be used. Selective cleavage
Tert-Butyloxycarbonyl protecting group
Tert-Butyloxycarbonyl_protecting_group
reactivity, as defined by relative rate constants, with the basicity of the nucleophile (relative to protons) and its polarizability. This equation was first
Edwards_equation
Group of nucleophilic compounds
Aluminium(I) nucleophiles are a group of inorganic and organometallic nucleophilic compounds containing at least one aluminium metal center in the +1 oxidation
Aluminium(I)_nucleophiles
Type of organocatalysis
is the simultaneous activation of both partners in a reaction, e.g. nucleophile and electrophile, termed "bifunctional catalysis". In all cases, the
Hydrogen-bond_catalysis
Chemical leaving group
previous bond with another species. For example, in the SN2 mechanism, a nucleophile attacks an organic compound containing the nucleofuge (the bromo group)
Nucleofuge
Type of aldol condensation reaction
containing a carbonyl group (C=O) acts both as the electrophile and the nucleophile in an aldol condensation. It is also called a symmetrical aldol condensation
Self-condensation
Lasting attraction between dissolved cations and anions in solution
incipient carbocation, while allowing the backside to be attacked by a nucleophile. This leads to a slight excess of the product with inverted stereochemistry
Intimate_ion_pair
Chemical reaction
of nitrogen gas. The isocyanate then undergoes attack by a variety of nucleophiles such as water, alcohols and amines, to yield a primary amine, carbamate
Curtius_rearrangement
Chemical reaction used to synthesize aryl halides from aryl diazonium salts
preparation of its diazonium salt followed by its displacement with a nucleophile in the presence of catalytic copper(I) salts. The most commonly employed
Sandmeyer_reaction
Organic chemical reaction
with sulfide or thioester electrophiles and boronic acid or stannane nucleophiles but many other coupling partners are viable. In addition to alkyl and
Liebeskind–Srogl_coupling
Chemical compound
however, reactions of nucleophiles with CO2 are highly reversible and products are only isolated with very strong nucleophiles, the reactions with CS2
Carbon_disulfide
Organic compound with a C=C–OH group
anions, which are important in organic reaction strategies as a strong nucleophile. Organic esters, ketones, and aldehydes with an α-hydrogen (C−H bond
Enol
Chemical changes in proteins following their translation from mRNA
modification are those that have a functional group that can serve as a nucleophile in the reaction: the hydroxyl groups of serine, threonine, and tyrosine;
Post-translational modification
Post-translational_modification
Functional group (C=O)
(aldehydes) > R2CO (ketones) > RCO2R' (esters) > RCONH2 (amides). A variety of nucleophiles attack, breaking the carbon-oxygen double bond. Interactions between
Carbonyl_group
Chemical compound
Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being
Phosphorus_trichloride
Chemical polarization due to intramolecular electron displacement
effect produced by the presence of a reagent like an electrophile or a nucleophile, IUPAC does not define it as such. The term electromeric effect is no
Electromeric_effect
Organic compound with a –C(=O)Cl group
react with carbon nucleophiles, such as Grignards and enolates, although mixtures of products can result. While a carbon nucleophile will react with the
Acyl_chloride
Chemical reaction
addition of a nucleophile to the β-position followed by trapping of the resulting enolate with an electrophile at the α-position. When the nucleophile is an enolate
Vicinal_difunctionalization
Inorganic compound (KOH)
Potassium hydroxide is an inorganic compound with the formula KOH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a
Potassium_hydroxide
Chemical compound
Diisopropylamine is a common amine nucleophile in organic synthesis. Because it is bulky, it is a more selective nucleophile than other similar amines, such
Diisopropylamine
Type of chemical reaction
equilibrium driven to the right by the acidic conditions. This enol is a nucleophile, which attacks an activated carbonyl group in a second molecule in step
Aldol_condensation
Type of organometallic reaction
all of the original ligand to be removed from the metal along with the nucleophile. While nucleophilic abstraction of an alkyl group is relatively uncommon
Nucleophilic_abstraction
Oxidation reaction in organic chemistry
halide substituent in the diazirine product can be displaced by a various nucleophiles. Graham, W. H. (1965-10-01). "The Halogenation of Amidines. I. Synthesis
Graham_reaction
Chemical reaction
substitutions: the amine is the first nucleophile displacing the bromine atom which then acts as the second nucleophile. In following the mechanism is described
Von_Braun_reaction
Chemical reaction of an alkene with mercuric acetate to form an alcohol
very reactive electrophile. The nucleophile will attack the mercuronium ion at this time. Therefore, the nucleophile attacks the more substituted carbon
Oxymercuration_reaction
Chemical compounds containing C–Li bonds
to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium
Organolithium_reagent
Chemical compound
acid with HATU to form the OAt-active ester; then (2) addition of the nucleophile (amine) to the active ester solution to afford the acylated product.
HATU
Chemical reaction
In organic synthesis, cyanation is the attachment or substitution of a cyanide group on various substrates. Such transformations are high-value because
Cyanation
Rearrangement of β-halo ketones and cyclobutanones
of a base, yielding a carboxylic acid derivative corresponding to the nucleophile (most often the base itself). E1cb will occur if α-carbon adjacent to
Homo-Favorskii_rearrangement
Organic compound (C6H5NH2); simplest aromatic amine
reactions. Like other amines, aniline is both a base (pKaH = 4.6) and a nucleophile, although less so than structurally similar aliphatic amines. Because
Aniline
Molecule containing main group elements with more than eight valence electrons
exhibited a dependence on the magnitude of charge on the oxygen of the nucleophile. Taken together this led the group to propose a reaction mechanism in
Hypervalent_molecule
Chemical reactions by which metal amine complexes exchange ligands
][\mathrm {OH} ^{-}]} The rate law is deceptive: hydroxide serves not as a nucleophile but as a base to deprotonate the coordinated ammonia. Simultaneously
SN1CB_mechanism
Conjugate base of an alcohol
Alkoxides are strong bases[citation needed] and, when R is not bulky, good nucleophiles and good ligands. Alkoxides, although generally not stable in protic
Alkoxide
Organic compound with a –C≡N functional group
hydrocyanic acid to aldehydes and ketones and discovered that the actual nucleophile is the cyanide ion, such that the addition of a base increases the reaction
Nitrile
Type of chemical reaction
vigorously with water and other nucleophiles (sometimes dangerously); they are easily quenched by other nucleophiles besides the desired alcohol; their
Fischer–Speier_esterification
the linear dimerization of 1,3-dienes with simultaneous addition of a nucleophile in a catalytic reaction. The reaction was independently discovered by
Telomerization_(dimerization)
Chemical group (>C=N=N)
In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic
Diazo
NUCLEOPHILE
NUCLEOPHILE
NUCLEOPHILE
NUCLEOPHILE
Boy/Male
Hindu, Indian
Lord Shiva
Male
Hindi/Indian
(अनिल) Hindi myth name of a god of the wind, ANIL means "air, wind."
Female
English
Modern English creation, possibly an elaborated form of Hebrew Tal, TALISHA means "dew."
Boy/Male
Arabic, Indian, Muslim
Charity
Surname or Lastname
English (south and south Midlands)
English (south and south Midlands) : variant spelling of Laing.
Boy/Male
Greek
Apostle.
Boy/Male
Hindu
Fearsome
Boy/Male
English American
Armed with a spear.
Girl/Female
American, Australian, British, Dutch, English, French, German, Latin, Spanish, Swedish
Beauty of Form; Charm; Love and Protection of God; Unmerited Favor; Graceful; Favor; Blessing; Good will
Girl/Female
Indian
Wild rose, Blue scented flower
NUCLEOPHILE
NUCLEOPHILE
NUCLEOPHILE
NUCLEOPHILE
NUCLEOPHILE