Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 20, Pages 10025-10032Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01618
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Funding
- National Science Foundation [CHE-1262254]
- Texas Christian University Invests in Scholarship (TCU-IS) Program
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1262254] Funding Source: National Science Foundation
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Phosphinylidene compounds (RRP)-R-1-P-2(O)H are important functionalities in organophosphorus chemistry and display prototropic tautomerism. Quantifying the tautomerization rate is paramount to understanding these compounds' tautomerization behavior, which may impact their reactivities in various reactions. We report a combined theoretical and experimental study of the initial tautomerization rate of a range of phosphinylidene compounds. Initial tautomerization rates are found to decrease in the order H3PO2 > Ph2P(O)H (PhO)(2)P(O)H > PhP(O) (OAlk)H > AlkP(O)(OAlk)H approximate to (AlkO)(2)P(O)H, where Alk denotes an alkyl substituent. The combination of computational investigations establishes a quantitative measure for the reactivity of various phosphorus compounds, as well as with experimental validation an accurate predictive tool.
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