The effects of t-butyl substituents on the thermodynamic stability of the cyclopentadienide ion

Add time:09/10/2019    Source:sciencedirect.com

The effects have been quantified of t-butyl substituents on the thermodynamic stability of cyclopentadienide ions with no, one, two, and three t-butyl groups, 1−, 2−, 3− and 4−, respectively. The stability estimated from oxidation potential values decreases in the order 1− (+ 0.04 V) >2− (− 0.16 V) >3− (− 0.28 V) >4− (−0.45 V). The stability evaluated from pKa values decreases in the same sequence (1H: 18.2, 2H: 19.9, 3H: 21.9, and 4H: 25.0 in DMSO). The t-butyl substituent reduces the thermodynamic stability of cyclopentadienide ion in step with increasing number of substituents and this is most probably due to a decrease in solvation and an increase in inductive effect in the carbanion.

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