Abstract
AbstractA detailed mechanism that features hydrogen‐bonded carbanions as well as free carbanions is presented for hydrogen transfer between carbon acids and methoxide ion in methanol. This is refined for several compounds by measuring their gas phase acidities, ΔG kcal/mol: C6H5CH(CF3)2 [335.3]; p‐C6H4CHClCF3 [337.4]; 9‐phenylfluorene [335.6]; C6F5H [349.2]. Ab initio molecular orbital calculations are reported to evaluate the stability of possible intermediates along the reaction pathway from 2‐hydro‐2‐phenyl‐perfluoropropane and methoxide ion to the carbanion and methanol. The intermediate, {C6H5C(CF3)2}−. HOCH3, is 6.8 kcal/mol more stable than the separated species, {C6H5C(CF3)2}− and CH3OH, and 43.2 kcal/mol more stable than C6H5CH(CF3)2 and −OCH3.
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 callMore From: Berichte der Bunsengesellschaft für physikalische Chemie
Disclaimer: 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.
