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Term in organic chemistry
term 2-norbornyl cation (or 2-bicyclo[2.2.1]heptyl cation) describes a carbonium ionic derivative of norbornane. A salt of the 2-norbornyl cation was crystallized
2-Norbornyl_cation
Any cation that has a pentavalent carbon atom
two-electron bonds. The more stable members are often bi- or polycyclic. The 2-norbornyl cation is one of the best-characterized carbonium ions. It is the prototype
Carbonium_ion
Ion with a positively charged carbon atom
of non-classical carbocations like the 2-norbornyl cation. According to the IUPAC, a carbocation is any cation containing an even number of electrons
Carbocation
Type of molecule in organic chemistry
/Springer 1977 [7] Moss, R.A. The 2-norbornyl cation: a retrospective J. Phys. Org. Chem. 2014, 27, 374-379 [8] 2-Norbornyl cation Neighbouring group participation
Nonclassical_ion
Chemical compound
a famous and illustrative use of tosylate as a leaving group, the 2-norbornyl cation was formed by an elimination reaction of 7-norbornenyl tosylate. The
P-Toluenesulfonic_acid
Chemical compound
stripping of the methyl groups from the parent molecule bornane. 2-Norbornyl cation Norbornene Norbornadiene endo-Norborneol exo-Norborneol Norcamphor
Norbornane
Electron-deficient chemical bond where three atoms share two electrons
and studied structure of this sort is the 2-Norbornyl cation. Three-center four-electron bond 2-Norbornyl cation Dihydrogen complex I. Mayer (1989). "Bond
Three-center two-electron bond
Three-center_two-electron_bond
Charged species in chemistry
to directly observe the 2-norbornyl cation by low-temperature NMR and confirm the presence of a non-classical 2-norbornyl cation, allowing the field to
Hydrogen-bridged_cations
Pharmaceutical compound
2C-G-5, also known as 3,4-norbornyl-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is one of several homologues
2C-G-5
Description of a molecule's true bond structure as a combination of structures
electrons (hyperconjugation) can be observed in the non-classical 2-Norbornyl cation Another example is methanium (CH+ 5). These can be viewed as containing
Resonance_(chemistry)
Chemical compound
undergo unusual substitution reactions owing to the generation of the 2-norbornyl cation. Being a strained ene, norbornenes react readily with thiols in the
Norbornene
Class of ions
(see Wagner-Meerwein shift). In especially favorable cases like the 2-norbornyl cation, hydrogen shifts may still take place at rates fast enough to interfere
Carbenium_ion
German inorganic chemist (born 1968)
Krossing's group, the first crystallographic characterization of the 2-norbornyl cation, a prototypical non-classical carbocation whose exact structure has
Karsten_Meyer_(chemist)
Organic reaction
"Stable carbocations, 189. The σ-bridged 2-norbornyl cation and its significance to chemistry". Acc. Chem. Res. 9 (2): 41–52. doi:10.1021/ar50098a001. Hogeveen
Wagner–Meerwein_rearrangement
Methods of hydrogenation and hydrogenolysis of organic compounds
1969). "Carbonium ion-silane hydride transfer reactions. II. 2-Phenyl-2-norbornyl cation". The Journal of Organic Chemistry. 34 (1): 4–6. doi:10.1021/jo00838a002
Reductions_with_hydrosilanes
Pharmaceutical compound
G-5, also known as 3,4-norbornyl-2,5-dimethoxyamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is one of several
G-5_(drug)
Chemistry of compounds with a carbon to cobalt bond
cobalt complexes with only alkyl ligands. Examples include Co(4-norbornyl)4 and its cation. Alkylcobalt is represented by vitamin B12 and related enzymes
Organocobalt_chemistry
American chemist (1924–2017)
Methylnorbornyl Cations. VI. The Stereochemistry of Vicinal Shift. Evidence for the Nonclassical Structure of 3-Methyl-2- norbornyl Cations," Journal of
Jerome_A._Berson
Hungarian-American chemist (1927–2017)
– such as the norbornyl cation, which can be depicted as cationic character delocalized over several bonds. Olah's studies of the cation with NMR spectroscopy
George_Andrew_Olah
Chemical compound
Co(C 5H 5) 2. Reaction of 1-norbornyllithium with the CoCl 2·THF produces tetrakis(1-norbornyl)cobalt(IV) — a rare example of a stable transition metal/saturated
Cobalt(II)_chloride
Canadian chemist (1912–1969)
Winstein reaction. He argued a non-classical cation was needed to explain the stability of the norbornyl cation. This fueled a debate with Herbert C. Brown
Saul_Winstein
Superacid system prepared from a Brønsted and a Lewis superacid
to investigate bridged carbocation systems. One controversial cation, the norbornyl cation, has been observed in several media, Magic acid among them. The
Magic_acid
Chemical element with atomic number 27 (Co)
dichloride is blue, the hydrate is red. The pink-colored cation hexaaquocobalt(II) [Co(H2O)6]2+ is found in several routine cobalt salts such as the nitrate
Cobalt
Chemistry of iron compounds containing a carbon-to-iron chemical bond
[(η3-allyl)Fe(CO)4]+X− are allyl cation synthons in allylic substitution. In contrast, compounds of the type [(η5-C5H5)Fe(CO)2(CH2CH=CHR)] possessing η1-allyl
Organoiron_chemistry
1991 book by Alexander Shulgin and Ann Shulgin
MMDA-3a (2-methoxy-3,4-methylendioxyamphetamine) MMDA-2 (2-methoxy-4,5-methylendioxyamphetamine) TMA (3,4,5-trimethoxyamphetamine) TMA-2 (2,4,5-trimethoxyamphetamine)
PiHKAL
Chemical property of transition metals
Cp*2Ti(C2H4) (16 e−) V(CO)6 (17 e−) Cp*Cr(CO)3 (17 e−) Pt(PtBu3)2 (14 e−) Co(norbornyl)4 (13 e−) [FeCp2]+ (17 e−) Sometimes such complexes engage in agostic
18-electron_rule
Class of chemical compounds
are known where the cyclohexyl base ring is replaced by rings such as norbornyl, adamantyl, tetralin, oxane, thiane or piperidine. Conformationally constrained
Arylcyclohexylamine
Affect on molecular properties due to spatial arrangement of electron orbitals
Shatavsky, M.; Norton, C.; Woodward, R. B. (1955). "7-Norbornenyl and 7-Norbornyl Cations". J. Am. Chem. Soc. 77 (15): 4183–4184. Bibcode:1955JAChS..77.4183W
Stereoelectronic_effect
Class of chemical compounds
class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen
DOx
Pharmaceutical compound
(3,4-trimethylene-2,5-DMA) G-4 (3,4-tetramethylene-2,5-DMA) G-5 (3,4-norbornyl-2,5-DMA) G-N Beatrice (N-methyl-DOM) N-Hydroxy-DOM (DOM-OH) DOM-NBOMe
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine
Family of phenethylamine psychedelics
the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic
2C_(psychedelics)
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