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The effect of hydrophobic‐lipophilic interactions on chemical reactivity: 7. Fourteen and eighteen‐membered‐ring neighboring group participations
Author(s) -
XiKui Jiang,
WeiQiang Fan,
YongZheng Hui,
JianHua Gu,
MingFang Chen
Publication year - 1987
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19870050113
Subject(s) - chemistry , ring (chemistry) , hydrolysis , reactivity (psychology) , chain (unit) , stereochemistry , group (periodic table) , medicinal chemistry , organic chemistry , medicine , physics , alternative medicine , pathology , astronomy
Hydrolytic rate constants of p ‐nitrophenyl esters of ω‐substituted straight chain acids with various chain lengths were measured in Φ=0.40, 0.45, 0.50, 0.55 Me 2 SO‐H 2 O mixtures. It has been demonstrated that for the long‐chain substrates 13‐SH and 17‐SH hydrophobic‐lipophilic forces can bring about 14‐membered‐ring and 18‐membered‐ring “neighboring group” participations in aggregating solvents. Twelve‐membered‐ring participation has not been observed for 11‐SH, indicating that tendencies towards self‐coiling and aggregating parallel each other.