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Influence of inductive effects and polarizability on the acid-base properties of alkyl compounds. Inversion of the alcohol acidity scale

✍ Scribed by J. Catalán

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
545 KB
Volume
9
Category
Article
ISSN
0894-3230

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✦ Synopsis

The inductive effects and polarizability of a series of 17 alkyl substituents were evaluated in theoretical terms from ab initio calculations for acid-base processes involving the corresponding alkanols. The effects allow one to account for general acid-base processes, both in the gas phase and in solution. Also, the classical inductive effect accounts for the acidity of dissolved alkanols and hence provides a straightforward explanation for the well known acidity inversion in alkanols from the gas phase to a solution. The applicability of the derived Z and P values for the alkyl groups to the protonation of amines, nitriles, ethers and thiols is shown.

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