Synthesis and structural studies of copper() complex with NS based -substituted pendant phosphonic acid arms
The synthesis of a heteromacrocyclic bifunctional chelator with phosphonic acid pendent arms is presented along copper( ii ) complexation. Ligand N 2 S 2 -POH featuring N , N ′-bis-substituted phosphonate pendent arms was isolated in respectable yields, characterized, and chelated to copper( ii ). I...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2020-03, Vol.49 (11), p.3545-3552 |
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| container_end_page | 3552 |
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| container_issue | 11 |
| container_start_page | 3545 |
| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 49 |
| creator | Taschner, Ian S Aubuchon, Ethan Schrage, Briana R Ziegler, Christopher J van der Est, Art |
| description | The synthesis of a heteromacrocyclic bifunctional chelator with phosphonic acid pendent arms is presented along copper(
ii
) complexation. Ligand
N
2
S
2
-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) (
N
2
S
2
-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 × 10
4
M
−1
. Heteromacrocycle
N
2
S
2
-POH
readily formed an encapsulated copper(
ii
) chelate at room temperature, which was examined through EPR analysis.
Physical properties and copper chelation of phosphonic acid substituted 14-[ane]N
2
S
2
macrocycle for use as a potential radio imaging ligand. |
| doi_str_mv | 10.1039/c9dt04869c |
| format | Article |
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ii
) complexation. Ligand
N
2
S
2
-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) (
N
2
S
2
-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 × 10
4
M
−1
. Heteromacrocycle
N
2
S
2
-POH
readily formed an encapsulated copper(
ii
) chelate at room temperature, which was examined through EPR analysis.
Physical properties and copper chelation of phosphonic acid substituted 14-[ane]N
2
S
2
macrocycle for use as a potential radio imaging ligand.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c9dt04869c</identifier><language>eng</language><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2020-03, Vol.49 (11), p.3545-3552</ispartof><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Taschner, Ian S</creatorcontrib><creatorcontrib>Aubuchon, Ethan</creatorcontrib><creatorcontrib>Schrage, Briana R</creatorcontrib><creatorcontrib>Ziegler, Christopher J</creatorcontrib><creatorcontrib>van der Est, Art</creatorcontrib><title>Synthesis and structural studies of copper() complex with NS based -substituted pendant phosphonic acid arms</title><title>Dalton transactions : an international journal of inorganic chemistry</title><description>The synthesis of a heteromacrocyclic bifunctional chelator with phosphonic acid pendent arms is presented along copper(
ii
) complexation. Ligand
N
2
S
2
-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) (
N
2
S
2
-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 × 10
4
M
−1
. Heteromacrocycle
N
2
S
2
-POH
readily formed an encapsulated copper(
ii
) chelate at room temperature, which was examined through EPR analysis.
Physical properties and copper chelation of phosphonic acid substituted 14-[ane]N
2
S
2
macrocycle for use as a potential radio imaging ligand.</description><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFjzFvwjAUhC1EpYa2S3ek1w2GtI4TQjMjEBML3SNjO4qrxLH8nkX5982A2g2G032nbzrGXjP-nvG8-lCVJl58lpWasCQr1uu0Enkx_WNRPrIZ4jfnQvCVSFh3vDhqDVoE6TQghagoBtmNGLU1CEMDavDehMVyhN535gfOllo4HOEk0WhIMZ6QLEUahzdOS0fg2wHHOKtAKqtBhh6f2UMjOzQv135i8932a7NPA6raB9vLcKn_L-T3_dstX3vd5L8c31dP</recordid><startdate>20200317</startdate><enddate>20200317</enddate><creator>Taschner, Ian S</creator><creator>Aubuchon, Ethan</creator><creator>Schrage, Briana R</creator><creator>Ziegler, Christopher J</creator><creator>van der Est, Art</creator><scope/></search><sort><creationdate>20200317</creationdate><title>Synthesis and structural studies of copper() complex with NS based -substituted pendant phosphonic acid arms</title><author>Taschner, Ian S ; Aubuchon, Ethan ; Schrage, Briana R ; Ziegler, Christopher J ; van der Est, Art</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c9dt04869c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>online_resources</toplevel><creatorcontrib>Taschner, Ian S</creatorcontrib><creatorcontrib>Aubuchon, Ethan</creatorcontrib><creatorcontrib>Schrage, Briana R</creatorcontrib><creatorcontrib>Ziegler, Christopher J</creatorcontrib><creatorcontrib>van der Est, Art</creatorcontrib><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Taschner, Ian S</au><au>Aubuchon, Ethan</au><au>Schrage, Briana R</au><au>Ziegler, Christopher J</au><au>van der Est, Art</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and structural studies of copper() complex with NS based -substituted pendant phosphonic acid arms</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><date>2020-03-17</date><risdate>2020</risdate><volume>49</volume><issue>11</issue><spage>3545</spage><epage>3552</epage><pages>3545-3552</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>The synthesis of a heteromacrocyclic bifunctional chelator with phosphonic acid pendent arms is presented along copper(
ii
) complexation. Ligand
N
2
S
2
-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) (
N
2
S
2
-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 × 10
4
M
−1
. Heteromacrocycle
N
2
S
2
-POH
readily formed an encapsulated copper(
ii
) chelate at room temperature, which was examined through EPR analysis.
Physical properties and copper chelation of phosphonic acid substituted 14-[ane]N
2
S
2
macrocycle for use as a potential radio imaging ligand.</abstract><doi>10.1039/c9dt04869c</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2020-03, Vol.49 (11), p.3545-3552 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_rsc_primary_c9dt04869c |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Synthesis and structural studies of copper() complex with NS based -substituted pendant phosphonic acid arms |
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