Original scientific paper

Solvolysis Rate of 3-Methyl-2- (3-pentynyl) · 2-cyclohexenyl p-Nitrobenzoate. A Model System for n-Participation of the CC Triple Bond

Mladen Ladika ; Department of Chemistry, Faculty of Science, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia
Dionis E. Sunko ; Department of Chemistry, Faculty of Science, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia
Stanko Borčić ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia

Abstract

The synthesis of 3-methyl-2-:(3-rpentynyl)-2-cycloheocenyl
p-nitro1benzoa1te is desc["ibed. This ester so1lvolyzes in 97°/o
CF3CH20H at 2'5 °C without n-participa:tion of the CC trLple
bond, showing solvoiysis rate retardaition in comparison with
the saturated anafog. This result is e~piained by electron-withdrawing
inductiove e1ffect 01f 1the CC trirple bond. The lo.g k va~ues
of alkanyl- (4), alikenyl- (5, 6), and alkyny:l-substitJu·ted (10)
esters show good linear correia1tion With the pK. values of the
cOirresrponding car:boxyJ'ic acids.

Keywords

Hrčak ID:

194149

URI

https://hrcak.srce.hr/194149

Publication date:

15.9.1984.

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