Which of the following best explains why thioesters have a greater free energy of hydrolysis than ordinary esters?
A)alcohols are better leaving groups than thiols
B)oxygen is more electronegative than sulfur
C)esters are resonance stabilized while thioesters are not
D)the oxygen of an ester is more easily protonated than the sulfur of a thioester
E)none of the above

Question

Quizplus · Accepted Answer

Thioesters lack the extensive resonance stabilization that esters benefit from due to the difference in orbital overlap between sulfur and carbon compared to oxygen and carbon. This makes thioesters less stable and thus they have a greater free energy of hydrolysis.

Which of the Following Best Explains Why Thioesters Have a Greater