The Alkaline Hydrolysis of Sulfonate Esters: Challenges in Interpreting Experimental and Theoretical Data

• Published in: Journal of organic chemistry Vol. 79; no. 7; pp. 2816 - 2828
• Main Authors: Duarte, Fernanda, Geng, Ting, Marloie, Gaël, Al Hussain, Adel O, Williams, Nicholas H, Kamerlin, Shina Caroline Lynn
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.04.2014; Amer Chemical Soc
• Subjects: alkaline hydrolysis; Alkaloids - chemistry; benzene; Benzenesulfonates - chemistry; benzenesulfonic acid; Chemistry; Chemistry, Organic; cleavage (chemistry); Cyclic N-Oxides - chemistry; Esters; Hydrolysis; Kinetics; Mesylates - chemistry; Models, Theoretical; Molecular Structure; organic chemistry; Physical Sciences; pyridines; Pyridines - chemistry; Pyridinium Compounds - chemistry; Science & Technology; thermodynamics; METAL-ION CATALYSIS; HAMMETT SUBSTITUENT CONSTANTS; ACCURATE EXPERIMENTAL VALUES; SULFATE ESTERS; ARYL BENZENESULFONATES; TRANSITION-STATE; DENSITY-FUNCTIONAL THEORY; PHOSPHATASE SUPERFAMILY; SOLVATION FREE-ENERGY; NUCLEOPHILIC DISPLACEMENT-REACTIONS

Sulfonate ester hydrolysis has been the subject of recent debate, with experimental evidence interpreted in terms of both stepwise and concerted mechanisms. In particular, a recent study of the alkaline hydrolysis of a series of benzene arylsulfonates (Babtie et al., Org. Biomol. Chem. 10, 2012, 809...