Abstract

Comparative acidity measurements have been performed between triphenylsilylpotassium and a series of arylmethanes by 1H-NMR in tetrahydrofuran: Ph 3 SiK+ Ar n CH 4 −n ⇆Ph 3 SiH+ Ar n CH 3 −n K Metalation of the arylmethane was complete in the case of Ph 3CH (p K a 31.4) and Ph 2CH 2 (p K a 33.4) but with ( p-CH 3·C 6H 4) 2CH 2 (p K a 35.1) ∼50% metalation of the di- p-tolymethane occurred, indicating that the two acids have equal p K a. No reaction occurred with 4-Ph·C 6H 4·CH 3 (p K a 38.7). Thus p K a Ph 3SiH≈35.1 in THF. This represents the first solution measurement of the acidity of an organosilane.

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 call

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.