Matches in SemOpenAlex for { <https://semopenalex.org/work/W2007361610> ?p ?o ?g. }
- W2007361610 endingPage "1114" @default.
- W2007361610 startingPage "1109" @default.
- W2007361610 abstract "A kinetic study on S N Ar reactions of 1-(4-nitrophenoxy)-2,4-dinitrobenzene (1a) with various anionic nucleophiles in 80 mol% water – 20 mol% DMSO at 25.0 °C is reported. The Brønsted-type plot for the reaction of 1a with a series of substituted phenoxides and HOO − results in an excellent linear correlation with β nuc = 1.17. However, OH − exhibits dramatic negative deviation from the Brønsted-type plot, while N 3 − , C 6 H 5 S − , and butane-2,3-dione monoximate (Ox − ) deviate positively from linearity. HOO − is 680-fold more reactive than OH − but does not exhibit the α-effect. In contrast, Ox − is 166-fold more reactive than isobasic 4-Cl − C 6 H 4 O − and exhibits the α-effect. Differential solvation effects have been suggested to be responsible for the α-effect in this study, i.e., Ox − exhibits the α-effect, since it is 5.7 kcal/mol less strongly solvated than 4-Cl − C 6 H 4 O − in the reaction medium, while HOO − does not show the α-effect due to a strong requirement for partial desolvation before nucleophilic attack. The highly enhanced reactivity of polarizable N 3 − and C 6 H 5 S − and extremely decreased reactivity of nonpolarizable OH − are in accord with the hard–soft acid and base principle." @default.
- W2007361610 created "2016-06-24" @default.
- W2007361610 creator A5007594566 @default.
- W2007361610 creator A5034892664 @default.
- W2007361610 creator A5080580572 @default.
- W2007361610 creator A5081827424 @default.
- W2007361610 creator A5088668565 @default.
- W2007361610 date "2015-10-01" @default.
- W2007361610 modified "2023-10-16" @default.
- W2007361610 title "The α-effect in the S<sub>N</sub>Ar reaction of 1-(4-nitrophenoxy)-2,4-dinitrobenzene with anionic nucleophiles: effects of solvation and polarizability on the α-effect" @default.
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