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Hyperconjugation can be used to rationalize a variety of chemical phenomena, including the anomeric effect, the gauche effect, the rotational barrier of ethane, the beta-silicon effect, the vibrational frequency of exocyclic carbonyl groups, and the relative stability of substituted carbocations and substituted carbon centred radicals, and the thermodynamic Zaitsev's rule for alkene stability.
A primary kinetic isotope effect (PKIE) may be found when a bond to the isotopically labeled atom is being formed or broken. [3] [4]: 427 Depending on the way a KIE is probed (parallel measurement of rates vs. intermolecular competition vs. intramolecular competition), the observation of a PKIE is indicative of breaking/forming a bond to the isotope at the rate-limiting step, or subsequent ...
Negative hyperconjugation is a theorized phenomenon in organosilicon compounds, in which hyperconjugation stabilizes or destabilizes certain accumulations of positive charge. The phenomenon explains corresponding peculiarities in the stereochemistry and rate of hydrolysis .
The α- and β-anomers of D-glucopyranose.. In organic chemistry, the anomeric effect or Edward-Lemieux effect (after J. T. Edward and Raymond Lemieux) is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to the heteroatom in the ring in, e.g., tetrahydropyran to prefer the axial orientation instead of the less-hindered equatorial orientation that ...
Negative hyperconjugation is seldom observed, though it can be most commonly observed when the σ *-orbital is located on certain C–F or C–O bonds. [ 3 ] [ 4 ] In negative hyperconjugation, the electron density flows in the opposite direction (from a π- or p-orbital to an empty σ * -orbital) than it does in the more common ...
Hydrogen-alpha, typically shortened to H-alpha or Hα, is a deep-red visible spectral line of the hydrogen atom with a wavelength of 656.28 nm in air and 656.46 nm in vacuum. It is the first spectral line in the Balmer series and is emitted when an electron falls from a hydrogen atom's third- to second-lowest energy level.
The Cieplak effect relies on the stabilizing interaction of mixing full and empty orbitals to delocalize electrons, known as hyperconjugation. [2] When the highest occupied molecular orbital of one system and the lowest unoccupied molecular orbital of another system have comparable energies and spatial overlap, the electrons can delocalize and sink into a lower energy level.
The alpha effect refers to the increased nucleophilicity of an atom due to the presence of an adjacent (alpha) atom with lone pair electrons. [2] This first atom does not necessarily exhibit increased basicity compared with a similar atom without an adjacent electron-donating atom, resulting in a deviation from the classical Brønsted-type ...