Abstract
AbstractThe solvolysis of a series of 1‐aryl‐2,2‐dimethyl‐1‐phenyl‐1‐propyl p‐nitrobenzoates (6a‐6g) in a variety of solvents were studied. Both the single‐parameter Hammett‐Brown equation (Eqn. 1) and the dual‐parameter Yukawa‐Tsuno equation (Eqn. 2) showed excellent linear correlations, although inverse order of k(p‐CF3)/k(m‐CF3) was realized in five different solvent systems. A similar result was also found in 3‐aryl‐2,2,4,4‐tetramethyl‐3‐pentyl p‐nitrobenzoates (5) in 80% acetone. The result of Grunwald‐Winstein type correlation analysis against YBnOPNB or YxBnOPNB showed ambiguity for interpretation. It provides more evidence for the lack of coplanarity between the aryl ring and the sp2 plane at the cationic transition state, and thus an insignificant resonance contribution from the aromatic moiety. A comprehensive collection of published data is tabulated.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
