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Elements and Compounds

Is triethylamine a better nucleophile than ethanol?


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November 26, 2009 9:53PM

No, Nucleophilicity is not the same thing as basiscity. Although Triethylamine is a strongerbase it is a far worse nucleophile. Nucleophilicity is dependent on sterics and whethe the incoming nuclophile can form a stable complex. In the case of triethylamine any complex formed will have a fomal positive charge on the Nitrogen and because all of its substituents are alkyl groups it can not loose them to become neutral. Ethanol on the other hand can loose a proton to form an ethoxide linkage and is the bette nucleophile but weaker base