Reduction of ormaplatin by an extended series of thiols unravels a remarkable correlation

2018 ◽  
Vol 47 (16) ◽  
pp. 5548-5552 ◽  
Author(s):  
Jingran Dong ◽  
Hongwu Tian ◽  
Changying Song ◽  
Tiesheng Shi ◽  
Lars I. Elding
Keyword(s):  
Free Energy ◽  
Energy Correlation ◽  
Linear Free Energy

Reduction of the Pt(iv) anticancer active prodrug ormaplatin by an extended series of thiols has been studied, revealing a remarkable linear free-energy correlation.

Correlation of the effects of alkyl substituents on the basicities of indoles

1992 ◽  
Vol 70 (1) ◽  
pp. 282-284 ◽  
Author(s):  
Peter A. Cohen ◽  
Louis A. Cohen
Keyword(s):  
Free Energy ◽  
Double Bond ◽  
Substituent Effects ◽  
Energy Correlation ◽  
Linear Free Energy ◽  
Alkyl Groups ◽  
Stabilization Parameter ◽  
Opposing Effects ◽  
Isomeric Mono

Alkyl groups at C-2 of indole increase basicity at the site of protonation, C-3, while alkyl groups at C-3 decrease basicity. These opposing effects can be incorporated, for both the isomeric mono- and 2,3-dialkylindoles, into a single linear free energy correlation, pKa = −10.05Σσ −3.94, in which [Formula: see text] and Ds is the double bond stabilization parameter at C-3. An analogous correlation for N-methylindoles, pKa = −8.64Σσ −2.80, reveals that the effect of N-alkylation on basicity is predictable but not additive. Keywords: alkylindoles, carbon basicity, free energy correlation, substituent effects, N-alkyl effect.

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