Reductively Stable Hydrogen-Bonding Ligands Featuring Appended CF 2 -H Units
We present the development of ligands featuring the unconventional hydrogen bond donor, -CF H, within a metal's secondary coordination sphere. When metalated with palladium, CF H-functionalized 1,10-phenanthroline provides highly directed H-bonding interactions with Pd-coordinated substrates. S...
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| Veröffentlicht in: | Journal of the American Chemical Society 2020-05, Vol.142 (19), p.8809-8817 |
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| container_issue | 19 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 142 |
| creator | Shanahan, James P Mullis, Danielle M Zeller, Matthias Szymczak, Nathaniel K |
| description | We present the development of ligands featuring the unconventional hydrogen bond donor, -CF
H, within a metal's secondary coordination sphere. When metalated with palladium,
CF
H-functionalized 1,10-phenanthroline provides highly directed H-bonding interactions with Pd-coordinated substrates. Spectroscopic and computational analyses with a series of
-type ligand acceptors (-F, -Cl, -Br, -OR) establish the H-bonding interaction strength for the -CF
H group (∼3 kcal/mol). The synthesis of Pd
/Ni
complexes and subsequent coupling (Ni) highlight the unique reductive and base compatibility of the -CF
H hydrogen bond donor group. |
| doi_str_mv | 10.1021/jacs.0c01718 |
| format | Article |
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H, within a metal's secondary coordination sphere. When metalated with palladium,
CF
H-functionalized 1,10-phenanthroline provides highly directed H-bonding interactions with Pd-coordinated substrates. Spectroscopic and computational analyses with a series of
-type ligand acceptors (-F, -Cl, -Br, -OR) establish the H-bonding interaction strength for the -CF
H group (∼3 kcal/mol). The synthesis of Pd
/Ni
complexes and subsequent coupling (Ni) highlight the unique reductive and base compatibility of the -CF
H hydrogen bond donor group.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.0c01718</identifier><identifier>PMID: 32352797</identifier><language>eng</language><publisher>United States</publisher><subject>Coordination Complexes - chemical synthesis ; Coordination Complexes - chemistry ; Hydrocarbons, Fluorinated - chemistry ; Hydrogen Bonding ; Ligands ; Molecular Structure ; Nickel - chemistry ; Palladium - chemistry</subject><ispartof>Journal of the American Chemical Society, 2020-05, Vol.142 (19), p.8809-8817</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1037-e06d6b90ad86fe21c5a9e0c686be720e3eb368cdfc8567d39d836a68bab594a13</citedby><cites>FETCH-LOGICAL-c1037-e06d6b90ad86fe21c5a9e0c686be720e3eb368cdfc8567d39d836a68bab594a13</cites><orcidid>0000-0003-4743-0000 ; 0000-0002-1296-1445 ; 0000-0002-3305-852X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,2763,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32352797$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shanahan, James P</creatorcontrib><creatorcontrib>Mullis, Danielle M</creatorcontrib><creatorcontrib>Zeller, Matthias</creatorcontrib><creatorcontrib>Szymczak, Nathaniel K</creatorcontrib><title>Reductively Stable Hydrogen-Bonding Ligands Featuring Appended CF 2 -H Units</title><title>Journal of the American Chemical Society</title><addtitle>J Am Chem Soc</addtitle><description>We present the development of ligands featuring the unconventional hydrogen bond donor, -CF
H, within a metal's secondary coordination sphere. When metalated with palladium,
CF
H-functionalized 1,10-phenanthroline provides highly directed H-bonding interactions with Pd-coordinated substrates. Spectroscopic and computational analyses with a series of
-type ligand acceptors (-F, -Cl, -Br, -OR) establish the H-bonding interaction strength for the -CF
H group (∼3 kcal/mol). The synthesis of Pd
/Ni
complexes and subsequent coupling (Ni) highlight the unique reductive and base compatibility of the -CF
H hydrogen bond donor group.</description><subject>Coordination Complexes - chemical synthesis</subject><subject>Coordination Complexes - chemistry</subject><subject>Hydrocarbons, Fluorinated - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Ligands</subject><subject>Molecular Structure</subject><subject>Nickel - chemistry</subject><subject>Palladium - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kF1LwzAYhYMobk7vvJb8ADPfJGuSXs5inVAQ1F2XfLwtHVtXmk7Yv9_GpleHc3g4Fw8hjxymHAR_WVkfp-CBa26uyJgnAljChbomYwAQTBslR-QuxtWxzoTht2QkhUyETvWYFF8Ydn5ofnG9p9-DdWuki33otzW27HXbhqatadHUtg2R5miHXX9a5l2HbcBAs5wKyhZ02TZDvCc3lV1HfLjkhCzzt59swYrP949sXjDPQWqGoIJyKdhgVIWC-8SmCF4Z5VALQIlOKuND5U2idJBpMFJZZZx1STqzXE7I8_nX99sYe6zKrm82tt-XHMqTlPIkpbxIOeJPZ7zbuQ2Gf_jPgjwAkhJc8A</recordid><startdate>20200513</startdate><enddate>20200513</enddate><creator>Shanahan, James P</creator><creator>Mullis, Danielle M</creator><creator>Zeller, Matthias</creator><creator>Szymczak, Nathaniel K</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-4743-0000</orcidid><orcidid>https://orcid.org/0000-0002-1296-1445</orcidid><orcidid>https://orcid.org/0000-0002-3305-852X</orcidid></search><sort><creationdate>20200513</creationdate><title>Reductively Stable Hydrogen-Bonding Ligands Featuring Appended CF 2 -H Units</title><author>Shanahan, James P ; Mullis, Danielle M ; Zeller, Matthias ; Szymczak, Nathaniel K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1037-e06d6b90ad86fe21c5a9e0c686be720e3eb368cdfc8567d39d836a68bab594a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Coordination Complexes - chemical synthesis</topic><topic>Coordination Complexes - chemistry</topic><topic>Hydrocarbons, Fluorinated - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Ligands</topic><topic>Molecular Structure</topic><topic>Nickel - chemistry</topic><topic>Palladium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shanahan, James P</creatorcontrib><creatorcontrib>Mullis, Danielle M</creatorcontrib><creatorcontrib>Zeller, Matthias</creatorcontrib><creatorcontrib>Szymczak, Nathaniel K</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shanahan, James P</au><au>Mullis, Danielle M</au><au>Zeller, Matthias</au><au>Szymczak, Nathaniel K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reductively Stable Hydrogen-Bonding Ligands Featuring Appended CF 2 -H Units</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J Am Chem Soc</addtitle><date>2020-05-13</date><risdate>2020</risdate><volume>142</volume><issue>19</issue><spage>8809</spage><epage>8817</epage><pages>8809-8817</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>We present the development of ligands featuring the unconventional hydrogen bond donor, -CF
H, within a metal's secondary coordination sphere. When metalated with palladium,
CF
H-functionalized 1,10-phenanthroline provides highly directed H-bonding interactions with Pd-coordinated substrates. Spectroscopic and computational analyses with a series of
-type ligand acceptors (-F, -Cl, -Br, -OR) establish the H-bonding interaction strength for the -CF
H group (∼3 kcal/mol). The synthesis of Pd
/Ni
complexes and subsequent coupling (Ni) highlight the unique reductive and base compatibility of the -CF
H hydrogen bond donor group.</abstract><cop>United States</cop><pmid>32352797</pmid><doi>10.1021/jacs.0c01718</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-4743-0000</orcidid><orcidid>https://orcid.org/0000-0002-1296-1445</orcidid><orcidid>https://orcid.org/0000-0002-3305-852X</orcidid></addata></record> |
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| source | MEDLINE; ACS Publications |
| subjects | Coordination Complexes - chemical synthesis Coordination Complexes - chemistry Hydrocarbons, Fluorinated - chemistry Hydrogen Bonding Ligands Molecular Structure Nickel - chemistry Palladium - chemistry |
| title | Reductively Stable Hydrogen-Bonding Ligands Featuring Appended CF 2 -H Units |
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