Asked in Elements and Compounds
Is triethylamine a better nucleophile than ethanol?
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