![Author ORCID: We display the ORCID iD icon alongside authors names on our website to acknowledge that the ORCiD has been authenticated when entered by the user. To view the users ORCiD record click the icon. [opens in a new tab]](https://chemrxiv.org/engage/assets/public/chemrxiv/images/logos/orcid.png)
Abstract
Reaction rates of strained cycloalkynes and cycloalkenes with 1,2-quinones were quantified by stopped flow UV-Vis spectroscopy. Surprisingly, it was determined that 8-membered BCN-OH reacts substantially (16 times) faster than the more strained 7-membered THS. Thermodynamic activation parameters, obtained from the linearized Eyring equation and stopped-flow measurements, revealed that the reaction of both BCN-OH and THS with ortho-quinones is entropycontrolled, ruling out a relevant contribution of secondary orbital interactions (SOIs) as earlier proposed.
Supplementary materials
Title
Supporting Information for High Rates of Quinone-Alkyne Cycloaddition Reactions are Dictated by Entropic Factors
Description
Details on the synthesis and characterization of THS 2 and carbamate derivatives 4 and 6, the setup used for the stopped-flow experiments, data on all kinetic measurements, derivatization of mathematical equations and specifics of the computational studies.
Actions
