Proton affinity and gas-phase basicity of pyrogallol and phloroglucinol: a computational study. Issue 1 (4th February 2021)

• Record Type: Journal Article
• Authors: Mayhan, Collin M.; Kumari, Harshita; Maddalena, Julia M.; Borgmeyer, Gabriel N.; Deakyne, Carol A.
• Is Part Of: Journal of coordination chemistry. Volume 74:Issue 1/3(2021)
• Page Start: 61
• Page End: 73
• Publication Date: 2021-02-04
• Subjects: 1, 2, 3-Benzenetriol -- 1, 3, 5-benzenetriol -- MP2 and DFT calculations -- initial and final state effects -- ortho -- para-directors; Coordination compounds -- Periodicals; 541.2242
• DOI: 10.1080/00958972.2021.1883007
• Languages: English
• ISSNs: 0095-8972

Abstract

Abstract: We report the proton affinities (PAs) and gas-phase basicities (GBs) of pyrogallol (1, 2, 3-trihydroxybenzene) and phloroglucinol (1, 3, 5-trihydroxybenzene), as determined by high level quantum chemical calculations and a series of isodesmic proton transfer reactions. These yet unmeasured values have relevance to release of active species from nanocarriers derived from the calixarene family of macrocycles. The PAs and GBs obtained for these two trihydroxybenzene isomers are compared and contrasted with those obtained previously for the third isomer, hydroxyquinol (1, 2, 4-trihydroxybenzene). Preferred protonation sites and relative thermochemical values are analyzed in terms of electron delocalization effects and the consequent disruption of intramolecular hydrogen bonding. Graphical Abstract: