Under favourable conditions, the phosphorus centres in tetraorganophosphonium cations are sufficiently electrophilic to become hypercoordinate by reaction with strong nucleophiles. However, as a peri substituent at the naphthalene system, such a centre proved to be unable to induce the nitrogen of a peri-bound dialkylamino group to bond formation. The distortion of the naphthalene skeleton revealed by X-ray structure determination of four 8-dialkylaminonaphth- 1-yl phosphonium salts does not exhibit the criteria of N-P bond formation but rather those of intersubstituent repulsion.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.