Ligands bearing soft donors including N- and S- have found applications in selective metal recovery due to the ability to preferentially bind soft acceptors like Ag+. Herein, N-(2-((4-vinylbenzyl)thio)ethyl)acetamide (L) bearing potential Ag+-selective N- and S-donors was prepared in a 76% yield under mild conditions. Reaction of L with silver perchlorate and silver nitrate gave complexes 1 and 2, as pastes, in yields of 98 and 77%, respectively. Physico-chemical and spectroscopic characterizations confirmed the chemical compositions of L, 1 and 2. ESI–MS data indicated that 1 and 2 each contain both the [AgL]+ and [AgL2]+ types complexes. Binding studies carried out by Job plot and 1H NMR titration using silver perchlorate indicated that L interacts with Ag+ to form the [AgL]+ type complex and that the N- and S-donors may be responsible for binding Ag+. Finally, L was observed to demonstrate excellent selectivity and moderate efficiency (36%) for Ag+ extraction from an aqueous solution also containing Cu2+ and Pb2+.
This is a preview of subscription content, access via your institution.
Buy single article
Instant access to the full article PDF.
Price excludes VAT (USA)
Tax calculation will be finalised during checkout.
Inoue K, Ooshita Y, Itaya T, Nakahara H (1997) Silver ion-selective extraction and transport by polystyrene derivatives with pendant ethoxycyclotriphosphazene. Macromol Chem Phys 198:3173–3184
Aderibigbe AD, Crane RA, Lees MR, Clark AJ (2020) Selective uptake of Ag(I) from aqueous solutions using ionic liquid-modified iron oxide nanoparticles. J Nanoparticle Res 216:1–14
Pearson RG (1968) Hard and soft acids and bases, HSAB, part I: Fundamental principles. J Chem Educ 45:581–587
Daubinet A, Kaye PT (2002) Designer ligands. VIII. Thermal and microwave-assisted synthesis of silver(I)-selective ligands. Synth Commun 32:3207–3217
Aderibigbe AD (2019) Synthesis and application of some Ag(I)-selective ligands and iron oxide/Ag(I)-selective composite nanoparticles. The University of Warwick
Abul Haj M, Aakeröy CB, Desper J (2013) Silver(I) coordination chemistry: from 1-D chains to molecular rectangles. New J Chem 37:204–211
Young AG, Hanton LR (2008) Square planar silver(I) complexes: A rare but increasingly observed stereochemistry for silver(I). Coord Chem Rev 252:1346–1386
Aderibigbe AD, Clark AJ (2020) Synthesis, silver(I) extraction and silver (I) binding studies of novel N1, N3-bis(2-(benzylthio)ethyl)propanediamide derivatives. Chem Pap. https://doi.org/10.1007/s11696-020-01307-x
Fielding L (2000) Determination of association constants (Ka) from solution NMR data. Tetrahedron 56:6151–6170
Schazmann B, Diamond D (2007) Improved nitrate sensing using ion selective electrodes based on urea–calixarene ionophores. New J Chem 31:587–592
Sole KC, Hiskey JB (1992) Solvent extraction characteristics of thiosubstituted organophosphinic acid extractants. Hydrometallurgy 30:345–365
Toure M, Arrachart G, Duhamet J, Pellet-Rostaing S (2018) Tantalum and niobium selective extraction by alkyl-acetophenone. Metals (Basel) 8:1–11
Ho C, Lam C, Chan M et al (2013) Electrospray ionisation mass spectrometry: principles and clinical applications. Clin Biochem Rev 24:3–12
Renny JS, Tomasevich LL, Tallmadge EH, Collum DB (2013) Method of continuous variations: applications of job plots to the study of molecular associations in organometallic chemistry. Angew Chem Int Ed 52:11998–12013
Podyachev SN, Semenov VE, Syakaev VV et al (2014) Metal binding properties of pyrimidinophanes and their acyclic counterparts. RSC Adv 4:10228–10239
The authors would like to thank the Commonwealth Scholarship Commission, UK and the University of Warwick for funding the research under Grant No. NGCS-2015-448.
Conflict of interest
The authors declare that they have no conflict of interest.
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Aderibigbe, A.D., Clark, A.J. N,S-donor acetamide ligand: silver (I) binding and test silver (I) extraction studies. Transit Met Chem 46, 121–127 (2021). https://doi.org/10.1007/s11243-020-00428-2