title: Raman and NMR kinetics study of the formation of amidoamines containing N-hydroxyethyl groups and investigations on their Cu(II) complexes in water.
abstract: Three amidoamines containing the N-hydroxyethyl group (HOEt), namely (HOEt)2N(CH2)2C(O)NH2(1), [(HOEt)2N(CH2)2C(O)NH]2CH2(2) andHOEtN[(CH2)2C(O)NH2]2(3) have been synthesized by reacting diethanolamineHOEt2NH with acrylamide and N,N'-methylenebisacrylamide (respectively 1 and 2) and ethanolamineHOEtNH2with acrylamide (3). Four other compounds corresponding to 1 and 2, but derived from sec-amines Me2NH (4 and 5) and Et2NH (6 and 7) have been prepared for the sake of comparison of the spectroscopic features. All compounds have been obtained by the well-known aza-Michael addition between an N-nucleophile and an activated vinyl group. The reaction in water between diethanolamine and acrylamide leading to 1 has been monitored in situ by Raman and NMR spectroscopy, both techniques confirming second order kinetics and giving values for kinetic constants in excellent agreement. The coordination ability of 1 and 2 towards Cu2+in water has been studied by the Job's plot method. Spectroscopic data indicate that ligand 1 prevalently forms a 4:1 Ligand/Metal complex with a (N,O3) coordination set on the equatorial plane of Cu2+, whereas ligand 2, containing two amide functionalities bridged by a methylene group, appears able to form a 1:1 Ligand/Metal chelate species, again with a (N,O3) donor set around copper.
authors: Dipartimento di Chimica, University of Parma, Viale delle Scienze 17/A, 43124 Parma, Italy. Electronic address: laura.bergamonti@unipr.it.
authors: Laura
authors: L
authors: Bergamonti
authors: Dipartimento di Chimica, University of Parma, Viale delle Scienze 17/A, 43124 Parma, Italy. Electronic address: claudia.graiff@unipr.it.
authors: Claudia
authors: C
authors: Graiff
authors: Dipartimento di Chimica, University of Parma, Viale delle Scienze 17/A, 43124 Parma, Italy.
authors: Matteo
authors: M
authors: Tegoni
authors: Dipartimento di Chimica, University of Parma, Viale delle Scienze 17/A, 43124 Parma, Italy.
authors: Giovanni
authors: G
authors: Predieri
authors: Sorbonne Universités, MONARIS, UMR 8233 UPMC-CNRS, Université Pierre et Marie Curie Paris 6, 75252 Paris, France.
authors: Ludovic
authors: L
authors: Bellot-Gurlet
authors: Dipartimento di Fisica e Scienze della Terra, University of Parma, Viale delle Scienze 7/A, 43124 Parma, Italy.
authors: Pier Paolo
authors: PP
authors: Lottici
keywords: Amidoamines; Copper complexes; Job's plot; Raman monitoring; Reaction kinetics; aza-Michael addition