Electron-withdrawing trifluoromethyl groups in combination with hydrogen bonds in polyols: Brønsted acids, hydrogen-bond catalysts, and anion receptors

Alireza Shokri, Xue Bin Wang, Steven R Kass

Research output: Contribution to journalArticlepeer-review

50 Scopus citations

Abstract

Electron-withdrawing trifluoromethyl groups were characterized in combination with hydrogen-bond interactions in three polyols (i.e., CF 3CH(OH)CH2CH(OH)CF3, 1; (CF3) 2C(OH)C(OH)(CF3)2, 2; ((CF3) 2C(OH)CH2)2CHOH, 3) by pKa measurements in DMSO and H2O, negative ion photoelectron spectroscopy and binding constant determinations with Cl-. Their catalytic behavior in several reactions were also examined and compared to a Brønsted acid (HOAc) and a commonly employed thiourea ((3,5-(CF 3)2C6H3NH)2CS). The combination of inductive stabilization and hydrogen bonds was found to afford potent acids which are effective catalysts. It also appears that hydrogen bonds can transmit the inductive effect over distance even in an aqueous environment, and this has far reaching implications.

Original languageEnglish (US)
Pages (from-to)9525-9530
Number of pages6
JournalJournal of the American Chemical Society
Volume135
Issue number25
DOIs
StatePublished - Jun 26 2013

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