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Ion with a positively charged carbon atom
Carbocation is a general term for ions with a positively charged carbon atom. In the present-day definition given by the IUPAC, a carbocation is any even-electron
Carbocation
Rearrangement reaction in organic chemistry
phenyl carbocation > hydride > tertiary carbocation (if formed by migration) > secondary carbocation (if formed by migration) > methyl carbocation. {Why
Pinacol_rearrangement
Substitution reaction with a carbocation intermediate
accurately described using steady-state kinetics. The reaction involves a carbocation intermediate and is commonly seen in reactions of secondary or tertiary
SN1_reaction
Superacid system prepared from a Brønsted and a Lewis superacid
at McMaster University, and has been used by George Olah to stabilise carbocations and hypercoordinated carbonium ions in liquid media. Magic acid and other
Magic_acid
A pyramidal carbocation is a type of carbocation with a specific configuration. This ion exists as a third class, besides the classical and non-classical
Pyramidal_carbocation
Rule for predicting outcomes of some addition reactions
with water in an addition reaction to form an alcohol that involves carbocation formation. The hydroxyl group (OH) bonds to the carbon that has the greater
Markovnikov's_rule
Chemical reagent used to differentiate 1°, 2°, 3° Alcohols
of the corresponding carbocations. Tertiary carbocations are far more stable than secondary carbocations, and primary carbocations are the least stable(due
Lucas'_reagent
Chemical compound
tert-butanol is a tertiary alcohol, the relative stability of the tert-butyl carbocation in the step 2 allows the SN1 mechanism to be followed, whereas a primary
Tert-Butyl_chloride
Set of reactions to attach substituents to an aromatic ring
alkylating agents (ones for which carbocation rearrangement is degenerate), or alkylating agents that yield stabilized carbocations (e.g., benzylic or allylic
Friedel–Crafts_reaction
Organic reaction
A Wagner–Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon
Wagner–Meerwein_rearrangement
density with the central carbocation to stabilize it. Additionally, the surrounding sp3 hybridized carbons can stabilize the carbocation through hyperconjugation
Tertiary_carbon
Hungarian-American chemist (1927–2017)
reactivity of carbocations via superacids. For this research, Olah was awarded a Nobel Prize in Chemistry in 1994 "for his contribution to carbocation chemistry
George_Andrew_Olah
Chemical reaction where a molecule is turned into a structural isomer of itself
In organic chemistry, a rearrangement reaction is a broad class of organic reactions "that involves a change of connectivity". Usually the term rearrangement
Rearrangement_reaction
Interaction of an organic molecule's reaction center with unconjugated electrons
reaction}) this page is limited to neighbouring group effects seen with carbocations and SN2 reactions. In this type of substitution reaction, one group of
Neighbouring group participation
Neighbouring_group_participation
Class of ions
of carbocations, which is a general term for diamagnetic carbon-based cations. In parallel with carbenium ions is another subset of carbocations, the
Carbenium_ion
cations with the formula RCO+, where R = alkyl or aryl. They are a kind of carbocation. In acylium ions, the C-C-O linkage is linear. The oxygen and the central
Acylium_ions
Chemical reaction involving organic compounds
open to this oxocarbenium intermediate are: in blue: capture of the carbocation by water or any suitable nucleophile through 5 to the 1,3-adduct 6. in
Prins_reaction
Chemical reaction in which one functional group in a compound is replaced by another
involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic
Substitution_reaction
Chemical compound
leaving group, this generates the carbocation. In the second step, the chloride nucleophile attacks the carbocation to form the product. 2-Chlorobutane
2-Chlorobutane
Chemical compound
trans-fused carbon ring systems formed by a carbocation mediated cyclization. The remaining tertiary carbocation is quenched by a molecule of water. After
Forskolin
Chemical compound
an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes. Triphenylmethanol
Triphenylmethanol
Terpene hydrocarbon
limonene is formed from geranyl pyrophosphate, via cyclization of a neryl carbocation or its equivalent as shown. The final step involves loss of a proton
Limonene
Creating chemicals by radioactive decay
technique is a method to generate chemical species such as radicals, carbocations, and other potentially unstable covalent structures by radioactive decay
Decay_technique
Terms for the placement of chemical substituents relative to a double or triple bond
intermediate carbocation of the mechanism of a reaction must be on the more-substituted carbon, allowing the substituent to bond to the more-stable carbocation and
Syn_and_anti_addition
Chemical compound
2019-07-25. Naidu, Veluru Ramesh; Ni, Shengjun; Franzén, Johan (2015). "The Carbocation: A Forgotten Lewis Acid Catalyst". ChemCatChem. 7 (13): 1896–1905. doi:10
Triphenylcarbenium
Chemical reaction
deprotonation of the α-carbon. This results in the formation of a carbocation intermediate. The carbocation is then deprotonated resulting in the formation of a new
E1cB-elimination_reaction
Chemical reaction in which a nucleophile is affixed to the substrate
stabilize the charge on the carbocation through resonance and distribution of charge. In this case, tertiary carbocation will react faster than a secondary
Nucleophilic_substitution
Process that results in the interconversion of chemical species
(proton) attacks the double bond forming a carbocation, which then reacts with the nucleophile (bromine). The carbocation can be formed on either side of the
Chemical_reaction
Type of molecule in organic chemistry
27, 374-379 [8] 2-Norbornyl cation Neighbouring group participation Carbocation Steric effects Solvation Scholz, F.; Himmel, D.; Heinemann, F. W.; Schleyer
Nonclassical_ion
Organic chemical reaction
often initialised by the formation of a reactive intermediate such as: a carbocation by heterolysis in a nucleophilic rearrangement or anionotropic rearrangement
1,2-rearrangement
Transfer of an alkyl group from one molecule to another
transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating
Alkylation
Chemical rearrangement
stabilizing carbocation formation, the fragmentation becomes a viable reaction pathway. The reaction generates a nitrile and a carbocation, which is quickly
Beckmann_rearrangement
Rearrangement reaction in organic chemistry
This reaction proceeds by removal of the leaving group X forming a carbocation as electron deficient center. One of the adjacent alkyl groups then migrates
Semipinacol_rearrangement
Chemical compound
reacts with boron trifluoride to form an ionic complex containing a carbocation that can be used as a catalyst for isomerization and disproportionation
Isopropyl_fluoride
Topics referred to by the same term
chloride (PVC), one specific type of vinyl polymer Vinyl cation, a type of carbocation Vinyl group, a broad class of organic molecules in chemistry Vinyl polymer
Vinyl
Chemical compound
function. It even protonates some hydrocarbons to afford pentacoordinate carbocations (carbonium ions). Like its precursor hydrogen fluoride, it attacks glass
Fluoroantimonic_acid
Lasting attraction between dissolved cations and anions in solution
ions in solution may assist in the removal of a leaving group to form a carbocation which reacts in an SN1 fashion; similarly, the leaving group may associate
Intimate_ion_pair
Obsolete concept in chemistry
selectivity of the reaction of certain carbocations with azides and water. The very stable triphenylmethyl carbocation derived from solvolysis of the corresponding
Reactivity–selectivity principle
Reactivity–selectivity_principle
Organic cation
The vinyl cation is a carbocation with the positive charge on an alkene carbon. Its empirical formula of the parent ion is C 2H+ 3. Vinyl cation are invoked
Vinyl_cation
Substitution or elimination reaction where the nucleophile is a solvent
by intimate ion pairs, whereby the leaving anion remains close to the carbocation, effectively shielding it from an attack by the nucleophile. Particularly
Solvolysis
Chemical compound
leaving a carbocation on the tertiary carbon attached to the ring. A 1,3-hydride shift then takes place to give a more stable allylic carbocation. The final
Zingiberene
Chemical compound
of deprotecting Boc-protected amines. The use of triethylsilane as a carbocation scavenger in the presence of trifluoroacetic acid in dichloromethane
Di-tert-butyl_dicarbonate
Any cation that has a pentavalent carbon atom
a cation that has a pentacoordinated carbon atom. They are a type of carbocation. In older literature, the name "carbonium ion" was used for what is today
Carbonium_ion
Chemical reaction
and mesomeric effects that could stabilize or destabilize a potential carbocation in the SN1 pathway. Usage of hydrohalic acids takes advantage of the
Ether_cleavage
Addition of a proton to an atom, molecule, or ion, forming the conjugate acid
H2O ⇌ H3O+ + HSO− 4 The protonation of isobutene in the formation of a carbocation: (CH3)2C=CH2 + HBF4 ⇌ (CH3)3C+ + BF− 4 The protonation of ammonia in
Protonation
Chemical compound
peptide sequence at the global deprotection. TIPS is able to scavenge carbocations formed in the deprotection of a peptide as it can act as a hydride donor
Triisopropylsilane
Chemical compound
proceeds via the formation of a carbocation ((CH3)2CH+), which attacks another propylene unit, generating a new carbocation, etc. This kind of process affords
Tripropylene
Chemical compound
retro-semipinacol rearrangement, deprotonation next to the tertiary carbocation to form an alkene, sulfonation of the alkene intermediate, and finally
Camphorsulfonic_acid
American chemist and academic
the characterization of the lifetimes and thermodynamic stability for carbocation and carbanion intermediates of organic reactions in water and the determination
John_P._Richard
Molecular entity formed as an elementary step in a multi-step chemical reaction
of chemical trapping Radical Carbene Carbocation Carbanion Carbyne Benzyne (an aryne) Cations, often carbocations, serve as intermediates in electrophilic
Reaction_intermediate
Hypothesis in physical organic chemistry
the first transition state in a SN1 reaction. The stabilities of the carbocations formed by this dissociation are known to follow the trend tertiary >
Hammond's_postulate
Chemist
prominent chemist who submitted significant evidence for the existence of carbocation mechanisms in organic chemistry. He was born in 1887 in the town of North
Frank_C._Whitmore
Chemical reaction
nitrous acid followed by expulsion of nitrogen and formation of a primary carbocation. A rearrangement reaction with ring expansion forms a more stable oxonium
Tiffeneau–Demjanov rearrangement
Tiffeneau–Demjanov_rearrangement
Any onium ion containing a halogen atom carrying a positive charge
atom will rearrange to a carbocation. This usually occurs only when that carbocation is an allylic or a benzylic carbocation. Halonium ions were first
Halonium_ion
catalyzed dimerization of isobutene, a reaction that proceeds via the carbocation (CH3)3C+. The process also leads to some triisobutenes and tetraisobutenes
Diisobutene
Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')
from isobutene or isoamylene, which protonate to give relatively stable carbocations. Using ethanol and methanol with these two alkenes, four fuel-grade ethers
Ether
Electron-deficient chemical bond where three atoms share two electrons
donor-acceptor interactions over the C-Be-C core of a Be(0)-carbene adduct. Carbocation rearrangement reactions occur through three-center bond transition states
Three-center two-electron bond
Three-center_two-electron_bond
Chain-growth polymerization without the ability to terminate
from Higashimura, Sawamoto and Kennedy. Typically, generating a stable carbocation for a prolonged period of time is difficult, due to the possibility for
Living_polymerization
System of connected p-orbitals with delocalized electrons in a molecule
organic conjugated molecules are 1,3-butadiene, benzene, and allylic carbocations. The largest conjugated systems are found in graphene, graphite, conductive
Conjugated_system
Ion
acylium cation to give a benzenium carbocation. [RC≡O+][AlCl−4] + C6H6 → RC(=O)C6H+6][AlCl−4] The acylbenzenium carbocation releases a proton, generating the
Tetrachloroaluminate
Group of atoms giving a molecule characteristic properties
Hydrocarbons may form charged structures: positively charged carbocations or negative carbanions. Carbocations are often named -um. Examples are tropylium and triphenylmethyl
Functional_group
Chemical acid found in vinegar
production. Acetic acid is often used as a solvent for reactions involving carbocations, such as Friedel-Crafts alkylation. For example, one stage in the commercial
Acetic_acid
Chemical element with atomic number 31 (Ga)
anions, where X is a halogen. They also react with alkyl halides to form carbocations and GaX− 4. When heated to a high temperature, gallium(III) halides react
Gallium
Mechanism for nucleophilic substitution reactions
that the ion pair is not completely dissociated, and therefore no real carbocation is formed, which else would lead to a racemisation.[citation needed]
SNi
Type of organic chemical reaction
Ionization: the carbon-halogen bond breaks to give a carbocation intermediate. deprotonation of the carbocation. E1 typically takes place with tertiary alkyl
Elimination_reaction
nucleophile addition of the conjugate base to the carbocation, a neighboring C-H bond can interact with the carbocation to form the hydrogen bridge. In Sorensen's
Hydrogen-bridged_cations
(C 2H 6) minus one hydride ion (H− ). It is a carbocation; more specifically, a nonclassical carbocation. Ethenium has been observed in rarefied gases
Ethenium
leading to the carbocation. The consecutive Criegee Rearrangement is carried out in an acidic environment and an ester forms from the carbocation. This opens
Criegee_rearrangement
Chemical species that donates an electron pair
obtained by reactions of selected nucleophiles with selected electrophilic carbocations such as tropylium or diazonium cations: or (not displayed) ions based
Nucleophile
Chemical theory about acids and bases
rationalized through HSAB theory, as follows: in a SN1 reaction the carbocation (a hard acid) reacts with a hard base (high electronegativity) and in
HSAB_theory
Type of chemical reaction
leaves, forming a carbocation. Another water molecule completes the E1 reaction by removing the α-proton, resolving the carbocation and forming a double
Aldol_condensation
Chemical reaction
positive charge on X is transferred to the carbon-carbon bond, forming a carbocation during the formation of the C-X bond. In the second step of an electrophilic
Electrophilic_addition
Chemical substances containing carbon
and carbenes occur as short-lived intermediates. Ions of carbon are carbocations and carbanions are also short-lived. An important carbon property is
Carbon_compounds
Chemical phenomenon
the carbon-halogen bond breaking to give a carbocation intermediate, then the Deprotonation of the carbocation. For these two reactions, there are 3 possible
Evelyn_effect
Special type of hyperconjugation
than their first-row congeners; conversely they destabilize adjacent carbocations, and these effects reverse one atom over. For phosphorus and later elements
Negative hyperconjugation in silicon
Negative_hyperconjugation_in_silicon
Hydrocarbon compound containing one or more C=C bonds
catalyst. The first step in hydration often involves formation of a carbocation. The net result of the reaction will be an alcohol. The reaction equation
Alkene
German chemist (1879–1965)
1965. His greatest impact upon organic chemistry was to propose the carbocation 2 as a reactive intermediate, originally as a rationalization of the
Hans_Meerwein
Chemical compound
pyrophosphate, which releases pyrophosphate to give the terpinyl cation. This carbocation is the precursor to many terpenes and terpenoids. Its hydrolysis gives
Terpineol
Ion
fluoronium structure over the alternative rapidly equilibrating classical carbocation. Definitive structural proof of the symmetrical [C–F–C]+ was reported
Fluoronium
Protein-coding gene in humans
carbocation intermediates are used by organic chemists. The O-alkyl cleavage of the ester bond, assisted by an Fe(II) cofactor, creates a carbocation
RPE65
Chemical phenomenon within ring systems
loss of a leaving group and the migration of an endocyclic bond to the carbocation. Pinacol type rearrangements are often used for this type of contraction
Ring expansion and contraction
Ring_expansion_and_contraction
Term in organic chemistry
alkyl halides, amines) or reactive intermediates (e.g. alkyl radicals, carbocations). Secondary (chemistry) Tertiary (chemistry) Quaternary (chemistry)
Primary_(chemistry)
Extremely strong acid
providing an environment to create, maintain, and characterize carbocations. Carbocations are intermediates in numerous useful reactions such as those forming
Superacid
Organic compound with the structure >C(O–)2
hydroxyl group of a hemiacetal becomes protonated and is lost as water. The carbocation that is produced is then rapidly attacked by a molecule of alcohol. Loss
Acetal
Chemical compound
cycloartenol (compound 7 in diagram) is methylated by SAM to give a carbocation that undergoes a hydride shift and loses a proton to yield a compound
Β-Sitosterol
Concept in organic chemistry
Stability of carbocations: (CH3)3C+ > (CH3)2CH+ > (CH3)CH2+ > CH3+ The three C–H σ bonds of the methyl group(s) attached to the carbocation can undergo
Hyperconjugation
Awardee(s) George A. Olah (1927–2017) Hungarian American "for his contribution to carbocation chemistry"
1994_Nobel_Prizes
Ion of carbon with three hydrogens
), or as a methyl radical (•CH 3) with one electron removed. It is a carbocation and an enium ion, making it the simplest of the carbenium ions. Experiments
Methenium
Electrophilic addition of hydrogen halides to alkenes
by the alkene from the hydrogen halide (HX) to form the most stable carbocation (relative stability: 3°>2°>1°>methyl), as well as generating a halogen
Hydrohalogenation
Chemical compound
been used, provided that a trap is provided for the released benzyl carbocation. When the protected amine is treated by either of the above methods (i
Benzyl_chloroformate
Organic compound containing a –C(=O)OH group
method is effective for alkenes that generate secondary and tertiary carbocations, e.g. isobutylene to pivalic acid. In the Koch reaction, the addition
Carboxylic_acid
Organic reaction
state for breakdown of the Criegee intermediate (illustrated by the carbocation resonance structure of the Criegee intermediate). Keeping this structure
Baeyer–Villiger_oxidation
Petroleum conversion process
catalytic cracking process breaks large hydrocarbons by their conversion to carbocations, which undergo myriad rearrangements. Figure 2 is a very simplified schematic
Fluid_catalytic_cracking
Chemical reaction in which water is produced as a byproduct
sulfuric acid and certain zeolites. These reactions often proceed via carbocation intermediates as shown for the dehydration of cyclohexanol. Some alcohols
Dehydration_reaction
Hydrocarbon compound (C6H6)
nucleophilic that it undergoes substitution by acylium ions and alkyl carbocations to give substituted derivatives. The most widely practiced example of
Benzene
Method of determining aromaticity in organic molecules
7H+ 7), also with six π electrons, is so stable compared to a typical carbocation that its salts can be crystallized from ethanol. On the other hand, in
Hückel's_rule
Component of a petroleum refinery
the C8 carbocation formed in the primary reaction. The resulting C12 carbocation can continue to react with an olefin to form a larger carbocation. As with
Alkylation_unit
Chemical compound giving a proton or accepting an electron pair
crystalline hydronium "salts". They can also quantitatively stabilize carbocations. While Ka measures the strength of an acid compound, the strength of
Acid
Class of metallocene cations
that there was a stabilizing interaction between the metal center and carbocation. Although these metallocenylmethylium cations had been observed as intermediates
Group 8 metallocenylmethylium cation
Group_8_metallocenylmethylium_cation
the direction of George Olah, where he worked on characterizing stable carbocations in superacids. He also sits on several editorial boards of major scientific
G._K._Surya_Prakash
CARBOCATION
CARBOCATION
CARBOCATION
CARBOCATION
Surname or Lastname
English
English : perhaps a habitational name for someone who lived by a long strip of ground, Middle English langet (a derivative of lang ‘long’).
Boy/Male
Muslim
Famous
Boy/Male
Biblical
Paternity; voluntary.
Male
French
French form of Latin Seraphinus, SÉRAPHIN means "burning one" or "serpent."
Biblical
breakings; hopes
Boy/Male
Tamil
Dussalan | தà¯à®¸à¯à®¸à®¾à®²à®¨
One of the kauravas
Boy/Male
Tamil
Leader
Male
Dutch
, kingly, powerful; or, horn of the sun.
Girl/Female
Australian, Finnish
Form of Ilma
Boy/Male
Teutonic
Strong as an eagle.
CARBOCATION
CARBOCATION
CARBOCATION
CARBOCATION
CARBOCATION