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• W1971075052 abstract "The synthesis and characterization of [Cp(NO)(PPh3)Re(2,5-dimethyl-3-thienyl)carbene]+ (3H+(S)), a novel Fischer carbene complex, is described. 3H+(S) undergoes reversible deprotonation with a pKa of 2.64 in 50% MeCN−50% water (v/v). Rate constants for the deprotonation of 3H+(S) by carboxylate ions and by primary aliphatic and secondary alicyclic amines were determined. A major focus of this paper is a comparison of the kinetic and thermodynamic acidities of 3H+(S) with those of [Cp(NO)(PPh3)Re(2-thienyl)carbene]+, 1H+(S). The pKa of 1H+(S) (2.51) is virtually the same as that of 3H+(S). This appears to be the result of a fortuitous cancellation of acidity-reducing and acidity-enhancing factors, a conclusion supported by a computational study of gas phase acidities. An analysis of Brønsted plots indicates that the intrinsic rate constants for proton transfer are about 2 orders of magnitude lower for 3H+(S) than for 1H+(S). This reduction is the result of steric effects and of electronic effects connected with the imbalanced nature of the transition state." @default.
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• W1971075052 date "2006-07-25" @default.
• W1971075052 modified "2023-09-30" @default.
• W1971075052 title "Kinetic and Thermodynamic Acidity of [Cp(NO)(PPh₃)Re(2,5-dimethyl-3-thienyl)carbene]⁺. Transition State Imbalance and Intrinsic Barriers" @default.
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• W1971075052 doi "https://doi.org/10.1021/om0604369" @default.
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