Abstract
The second ionization energies of phenol and the isomeric dihydroxybenzenes as well as their methyl ethers are determined by means of charge-stripping mass spectrometry. Compared to the parent molecule benzene, introduction of a hydroxy substituent lowers the second ionization energy by ca. 0.6 eV, whereas a methoxy substituent exerts a much more pronounced effect of about 1.6 eV. With regard to disubstitution, the effects behave almost completely additive for the para-derivatives, whereas the ortho-compounds are stabilized only about half that much by the second substituent, and for the meta-derivatives the influence of a second donor substituent is even smaller. The trends observed highlight the role of quinoid resonance structures for the stabilization of the dicationic compounds.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
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.