What are the pKa values of organophosphorus compounds? |
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Authors: | Jia-Ning Li Yao Fu |
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Institution: | Department of Chemistry, University of Science and Technology of China, Hefei 230026, China |
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Abstract: | A first-principle theoretical protocol was developed, which could successfully predict the pKa values of a number of amines and thiols in DMSO with a precision of about 1.1 pKa unit. Using this protocol we calculated the pKa values of diverse types of organophosphorus compounds in DMSO. The accuracy of these predicted values was estimated to be about 1.1 pKa because phosphorus is in the same group as nitrogen and in the same period as sulfur. The theoretical predictions were also consistent with all the available experimental data. Thus, a scale of reliable pKa values was constructed for the first time for organophosphorus. These pKa values would be helpful to synthetic chemists who need to design the experimental conditions for handling deprotonated organophosphorus. On the basis of these pKa values we also studied, for the first time, some interesting topics such as the substituent effects on the pKa values of various types of organophosphorus, and the differences between the pKa values of organophosphorus and organic amines. |
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Keywords: | Organophosphorus pKa DMSO Ab initio |
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