Substitution or elimination reaction where the nucleophile is a solvent
In chemistry, solvolysis is a type of nucleophilic substitution (SN1/SN2) or elimination where the nucleophile is a solvent molecule.[1] Characteristic of SN1 reactions, solvolysis of a chiral reactant affords the racemate. Sometimes however, the stereochemical course is complicated by intimate ion pairs, whereby the leaving anion remains close to the carbocation, effectively shielding it from an attack by the nucleophile. Particularly fast reactions can occur by neighbour group participation, with nonclassical ions as intermediates or transition states.
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "solvolysis". doi:10.1351/goldbook.S05762
intermediates or transition states. For certain nucleophiles, solvolysis reactions are classified. Solvolysis involving water is called hydrolysis. Related terms...
substitution reactions at secondary carbons: Many reactions studied are solvolysis reactions where a solvent molecule (often an alcohol) is the nucleophile...
also act as nucleophiles, and the process is known as solvolysis. The Y scale correlates solvolysis reaction rates of any solvent (k) with that of a standard...
same uniform SN1-like mechanism. The solvolysis of several cyclopentyl and steroidal esters show that large solvolysis rates and differences between epimers...
have been generated in photochemical solvolysis reactions. The figure to the right depicts photochemical solvolysis of vinyl iodonium salt, through heterolytic...
This generally occurs in highly polar solvents through a process called solvolysis. The positively charged component then reacts with a nucleophile forming...
hexafluorophosphate ion is generally inert and hence a suitable counterion, its solvolysis can be induced by highly electrophilic metal centers. For example, the...
unsaturated tosylate will react more quickly (1011 times faster for aqueous solvolysis) with a nucleophile than the saturated tosylate. The carbocationic intermediate...
nucleophilic reactions with solvents such as alcohols and water are named solvolysis. Nucleophiles may take part in nucleophilic substitution, whereby a nucleophile...
expulsion of a leaving group to form a nitrilium ion. This is followed by solvolysis to an imidate and then tautomerization to the amide: This nitrilium ion...
solvent-shared ion pair results. The ion pair concept explains stereochemistry in solvolysis. The concept of intimate ion pairs is used to explain the slight tendency...
demonstrated a solvolysis reaction of the hexafluorophosphate ion. The tris(solvent) rhodium complex [(η5-C5Me5)Rh(Me2CO)3](PF6)2 undergoes solvolysis when heated...
process is referred to as solvolysis. The thermodynamic concept of solubility does not apply straightforwardly to solvolysis. When a solute dissolves,...
structure for C 4H+ 7 is supported by substantial experimental evidence from solvolysis experiments and NMR studies conducted in non-nucleophilic media. One or...
carbon atom. Part XXIII. A kinetic demonstration of the unimolecular solvolysis of alkyl halides. (Section E) a general discussion". Journal of the Chemical...
esters and amides can also be completely depolymerised by hydrolysis or solvolysis. This can be a purely chemical process but may also be promoted by enzymes...
Singleton A (February 2005). "Isotope effects, dynamics, and the mechanism of solvolysis of aryldiazonium cations in water". Journal of the American Chemical Society...
Kochi, Jay Kazuo (1952). The application of the Hammett equation to the solvolysis of benzyl tosylates (Ph.D.). Iowa State University. OCLC 908156744 – via...
relative to the starting material. The following table shows the relative solvolysis rates of tert-butyl chloride with acetic acid (CH3CO2H), methanol (CH3OH)...
H. H. Zeiss, he proposed the Doering-Zeiss mechanistic hypothesis for solvolysis reactions. He first articulated the notion that cyclic systems with (4n...
ion locked in a designed cage structure by Lectka and coworkers. Recent solvolysis experiments and NMR spectroscopic studies on a metastable [C–F–C]+ fluoronium...
as esters and amides can be completely depolymerised by hydrolysis or solvolysis. This can be a purely chemical process but may also be promoted by enzymes...
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