Synthesis and structural studies of copper(ii) complex with N2S2 based: N-substituted pendant phosphonic acid arms

Ian S. Taschner; Ethan Aubuchon; Briana R. Schrage; Christopher J. Ziegler; Art Van Der Est

doi:10.1039/c9dt04869c

Synthesis and structural studies of copper(ii) complex with N₂S₂ based: N-substituted pendant phosphonic acid arms

Ian S. Taschner, Ethan Aubuchon, Briana R. Schrage, Christopher J. Ziegler, Art Van Der Est

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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.

Original language	English
Pages (from-to)	3545-3552
Number of pages	8
Journal	Dalton Transactions
Volume	49
Issue number	11
DOIs	https://doi.org/10.1039/c9dt04869c
State	Published - Mar 21 2020
Externally published	Yes

Funding

Ohio Board of Regents for funds used to purchase the Bruker-Nonius Apex CCD X-ray diffractometer and National Science Foundation (CHE-0840446). We thank the Indiana University Bloomington Mass Spectrometry Facility for exact mass measurements.

Funders	Funder number
National Science Foundation	CHE-0840446

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title = "Synthesis and structural studies of copper(ii) complex with N2S2 based: N-substituted pendant phosphonic acid arms",

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.",

author = "Taschner, {Ian S.} and Ethan Aubuchon and Schrage, {Briana R.} and Ziegler, {Christopher J.} and {Van Der Est}, Art",

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T2 - 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

PY - 2020/3/21

Y1 - 2020/3/21

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.

AB - 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.

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M3 - Article

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AN - SCOPUS:85082093476

SN - 1477-9226

VL - 49

SP - 3545

EP - 3552

JO - Dalton Transactions

JF - Dalton Transactions

IS - 11

ER -

Synthesis and structural studies of copper(ii) complex with N₂S₂ based: N-substituted pendant phosphonic acid arms

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