TY - JOUR
T1 - Reactivity-selectivity relationships. Part 6. Application of the reactivity-selectivity principle to solvolytic reactions. Possible evidence for ion pair intermediates in SN2 solvolyses
AU - Pross, Addy
AU - Aronovitch, Haim
AU - Koren, Rodi
PY - 1978/1/1
Y1 - 1978/1/1
N2 - The reactivity-selectivity principle has been applied to the study of the solvolytic behaviour of octyl, 1-methylheptyl, and benzyl derivatives toward the competing nucleophiles, ethanol and water. Low selectivity values, k E/kW, are observed for these substrates. The results are interpreted as possible evidence for ion pair intermediates in SN2 solvolyses. The effect of changes in substrate, solvent polarity, leaving group, and temperature are consistent with this interpretation. In the presence of a strong nucleophile, such as azide ion, a traditional SN2 pathway is indicated.
AB - The reactivity-selectivity principle has been applied to the study of the solvolytic behaviour of octyl, 1-methylheptyl, and benzyl derivatives toward the competing nucleophiles, ethanol and water. Low selectivity values, k E/kW, are observed for these substrates. The results are interpreted as possible evidence for ion pair intermediates in SN2 solvolyses. The effect of changes in substrate, solvent polarity, leaving group, and temperature are consistent with this interpretation. In the presence of a strong nucleophile, such as azide ion, a traditional SN2 pathway is indicated.
UR - http://www.scopus.com/inward/record.url?scp=37049094478&partnerID=8YFLogxK
U2 - 10.1039/p29780000197
DO - 10.1039/p29780000197
M3 - Article
AN - SCOPUS:37049094478
SN - 0300-9580
SP - 197
EP - 204
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 3
ER -