title: The heterocyclic ring of 4-substituted-1,8-naphthalimides is NOT inert to nucleophilic attack, contrary to earlier reports.
abstract: The heterocyclic ring of N-aryl-4-chloro-1,8-naphthalimides, reported to be resistant to nucleophilic attack, reacts with primary amine nucleophiles at room temperature to give 4-chloro-N-alkyl-1,8-naphthalimides. The reaction is first order in the naphthalimide. The Hammett plot is linear (R(2) 0.996) with a large positive slope (+3.0), consistent with substantial negative charge development at nitrogen in the activated complex.
authors.affiliation: Department of Chemistry, University of Wisconsin-Eau Claire, Eau Claire, WI, USA.
authors.forename: Ryan K
authors.initials: RK
authors.lastname: McKenney
authors.forename: Leah L
authors.initials: LL
authors.lastname: Groess
authors.forename: Kyle M
authors.initials: KM
authors.lastname: Kopidlansky
authors.forename: Kelsey L
authors.initials: KL
authors.lastname: Dunkle
authors.forename: David E
authors.initials: DE
authors.lastname: Lewis
mesh_terms: D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D054879:Halogenation; D053644:Naphthalimides / Q000737:chemistry*
chemical_list: D000588:Amines; D053644:Naphthalimides