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Synthesis and structural studies of copper(ii) complex with N2S2 based N-substituted pendant phosphonic acid arms.
Dalton Trans. 2020 Mar 21; 49(11):3545-3552.DT

Abstract

The synthesis of a heteromacrocyclic bifunctional chelator with phosphonic acid pendent arms is presented along copper(ii) complexation. Ligand N2S2-POH featuring N,N'-bis-substituted phosphonate pendent arms was isolated in respectable yields, characterized, and chelated to copper(ii). Implementation of both Moedritzer-Irani and Kabachnik-Fields conditions using aza-thia macrocycle 1,8-dithia-4,11-diazacyclotetradecane afforded 1,8-dithia-4,11-diazacyclotetradecane-4,11-diyl-bis-(methylene)-bis-(phosphonic acid) (N2S2-POH). Kinetic NMR studies provided four acid dissociation constants with respect to hydronium ion concentration. Benesi-Hildebrand binding experiment provided a conditional formation constant of 2.8 × 104 M-1. Heteromacrocycle N2S2-POH readily formed an encapsulated copper(ii) chelate at room temperature, which was examined through EPR analysis.

Authors+Show Affiliations

Department of Chemistry, Indiana University Northwest, Gary, Indiana 46408, USA. itaschne@iu.edu.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32118216

Citation

Taschner, Ian S., et al. "Synthesis and Structural Studies of Copper(ii) Complex With N2S2 Based N-substituted Pendant Phosphonic Acid Arms." Dalton Transactions (Cambridge, England : 2003), vol. 49, no. 11, 2020, pp. 3545-3552.
Taschner IS, Aubuchon E, Schrage BR, et al. Synthesis and structural studies of copper(ii) complex with N2S2 based N-substituted pendant phosphonic acid arms. Dalton Trans. 2020;49(11):3545-3552.
Taschner, I. S., Aubuchon, E., Schrage, B. R., Ziegler, C. J., & van der Est, A. (2020). Synthesis and structural studies of copper(ii) complex with N2S2 based N-substituted pendant phosphonic acid arms. Dalton Transactions (Cambridge, England : 2003), 49(11), 3545-3552. https://doi.org/10.1039/c9dt04869c
Taschner IS, et al. Synthesis and Structural Studies of Copper(ii) Complex With N2S2 Based N-substituted Pendant Phosphonic Acid Arms. Dalton Trans. 2020 Mar 21;49(11):3545-3552. PubMed PMID: 32118216.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and structural studies of copper(ii) complex with N2S2 based N-substituted pendant phosphonic acid arms. AU - Taschner,Ian S, AU - Aubuchon,Ethan, AU - Schrage,Briana R, AU - Ziegler,Christopher J, AU - van der Est,Art, Y1 - 2020/03/02/ PY - 2020/3/3/pubmed PY - 2020/3/3/medline PY - 2020/3/3/entrez SP - 3545 EP - 3552 JF - Dalton transactions (Cambridge, England : 2003) JO - Dalton Trans VL - 49 IS - 11 N2 - The synthesis of a heteromacrocyclic bifunctional chelator with phosphonic acid pendent arms is presented along copper(ii) complexation. Ligand N2S2-POH featuring N,N'-bis-substituted phosphonate pendent arms was isolated in respectable yields, characterized, and chelated to copper(ii). Implementation of both Moedritzer-Irani and Kabachnik-Fields conditions using aza-thia macrocycle 1,8-dithia-4,11-diazacyclotetradecane afforded 1,8-dithia-4,11-diazacyclotetradecane-4,11-diyl-bis-(methylene)-bis-(phosphonic acid) (N2S2-POH). Kinetic NMR studies provided four acid dissociation constants with respect to hydronium ion concentration. Benesi-Hildebrand binding experiment provided a conditional formation constant of 2.8 × 104 M-1. Heteromacrocycle N2S2-POH readily formed an encapsulated copper(ii) chelate at room temperature, which was examined through EPR analysis. SN - 1477-9234 UR - https://www.unboundmedicine.com/medline/citation/32118216/Synthesis_and_structural_studies_of_copper(ii)_complex_with_N2S2_based_N-substituted_pendant_phosphonic_acid_arms L2 - https://doi.org/10.1039/c9dt04869c DB - PRIME DP - Unbound Medicine ER -
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