Premium
Cross‐interaction constants as a measure of the transition state structure. Part 9. The degree of bond formation in the S N 2 transition state involving anionic nucleophiles
Author(s) -
Lee Ikchoon,
Koh Han Joong,
Huh Chul,
Lee Hai Whang
Publication year - 1990
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610030809
Subject(s) - chemistry , nucleophile , substituent , reaction rate constant , aniline , medicinal chemistry , computational chemistry , photochemistry , kinetics , organic chemistry , catalysis , physics , quantum mechanics
The second‐order rate constants of the reactions between benzenesulphonyl chlorides and anionic nucleophiles, benzoates and cinnamates, in methanol at 30·0°C are reported. A marked increase in rate found with a p ‐nitro substituent in the substrate indicated the development of an electron‐rich centre on the S atom in the transition state. The two types of cross‐interaction constants, ρ xy and λ xy , suggested that bond formation in the S N 2 transition state with anionic nucleophiles is greater than that for the corresponding reaction with aniline nucleophiles.