Quantifying and understanding the electronic properties of N-heterocyclic carbenes
The use of N -heterocyclic carbenes (NHCs) in chemistry has developed rapidly over the past twenty years. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centres, and as organocatalysts able to mediate an exciting range of reactions. Ho...
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| Veröffentlicht in: | Chemical Society reviews 2013-01, Vol.42 (16), p.6723-6753 |
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| container_title | Chemical Society reviews |
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| creator | Nelson, David J Nolan, Steven P |
| description | The use of
N
-heterocyclic carbenes (NHCs) in chemistry has developed rapidly over the past twenty years. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centres, and as organocatalysts able to mediate an exciting range of reactions. However, the sheer number of NHCs known in the literature can make the appropriate choice of NHC for a given application difficult. A number of metrics have been explored that allow the electronic properties of NHCs to be quantified and compared. In this review, we discuss these various metrics and what they can teach about the electronic properties of NHCs. Data for approximately three hundred NHCs are presented, obtained from a detailed survey of the literature.
The wide range of NHCs known in the literature can make choosing an NHC for a given application difficult. In this review, the electronic properties of NHCs are discussed, as well as the various methods by which they can be quantified. Data for
ca.
three hundred NHCs are provided. |
| doi_str_mv | 10.1039/c3cs60146c |
| format | Article |
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N
-heterocyclic carbenes (NHCs) in chemistry has developed rapidly over the past twenty years. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centres, and as organocatalysts able to mediate an exciting range of reactions. However, the sheer number of NHCs known in the literature can make the appropriate choice of NHC for a given application difficult. A number of metrics have been explored that allow the electronic properties of NHCs to be quantified and compared. In this review, we discuss these various metrics and what they can teach about the electronic properties of NHCs. Data for approximately three hundred NHCs are presented, obtained from a detailed survey of the literature.
The wide range of NHCs known in the literature can make choosing an NHC for a given application difficult. In this review, the electronic properties of NHCs are discussed, as well as the various methods by which they can be quantified. Data for
ca.
three hundred NHCs are provided.</description><identifier>ISSN: 0306-0012</identifier><identifier>EISSN: 1460-4744</identifier><identifier>DOI: 10.1039/c3cs60146c</identifier><identifier>PMID: 23788114</identifier><language>eng</language><publisher>England</publisher><subject>Carbenes ; Electronic properties ; Excitation ; Ligands ; Metalorganic compounds</subject><ispartof>Chemical Society reviews, 2013-01, Vol.42 (16), p.6723-6753</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c434t-a131087452822985bfb0678d0c080f6a17c404f0932b48d6f829bedb80b6fb323</citedby><cites>FETCH-LOGICAL-c434t-a131087452822985bfb0678d0c080f6a17c404f0932b48d6f829bedb80b6fb323</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23788114$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nelson, David J</creatorcontrib><creatorcontrib>Nolan, Steven P</creatorcontrib><title>Quantifying and understanding the electronic properties of N-heterocyclic carbenes</title><title>Chemical Society reviews</title><addtitle>Chem Soc Rev</addtitle><description>The use of
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-heterocyclic carbenes (NHCs) in chemistry has developed rapidly over the past twenty years. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centres, and as organocatalysts able to mediate an exciting range of reactions. However, the sheer number of NHCs known in the literature can make the appropriate choice of NHC for a given application difficult. A number of metrics have been explored that allow the electronic properties of NHCs to be quantified and compared. In this review, we discuss these various metrics and what they can teach about the electronic properties of NHCs. Data for approximately three hundred NHCs are presented, obtained from a detailed survey of the literature.
The wide range of NHCs known in the literature can make choosing an NHC for a given application difficult. In this review, the electronic properties of NHCs are discussed, as well as the various methods by which they can be quantified. Data for
ca.
three hundred NHCs are provided.</description><subject>Carbenes</subject><subject>Electronic properties</subject><subject>Excitation</subject><subject>Ligands</subject><subject>Metalorganic compounds</subject><issn>0306-0012</issn><issn>1460-4744</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqN0M9LwzAUB_AgipvTi3el3kSovvxYmh5l-AuGoui5NOmLq3TtTNLD_nszNrebeHqPvA9fwpeQUwrXFHh-Y7jxEqiQZo8M44BUZELskyFwkCkAZQNy5P1X3Ggm2SEZMJ4pRakYkrfXvmxDbZd1-5mUbZX0bYXOh7iuXsIME2zQBNe1tUkWrlugCzX6pLPJczrDgK4zS9PEoymdxhb9MTmwZePxZDNH5OP-7n3ymE5fHp4mt9PUCC5CWlJOQWVizBRjuRprq0FmqgIDCqwsaWYECAs5Z1qoSlrFco2VVqCl1ZzxEblc58ZffffoQzGvvcGmKVvsel_QTEnGeA7_oIIyKjnkK3q1psZ13ju0xcLV89ItCwrFqu5iV3fE55vcXs-x2tLffiO4WAPnzfa6CygWlY3m7C_DfwA2WY-X</recordid><startdate>20130101</startdate><enddate>20130101</enddate><creator>Nelson, David J</creator><creator>Nolan, Steven P</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SP</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20130101</creationdate><title>Quantifying and understanding the electronic properties of N-heterocyclic carbenes</title><author>Nelson, David J ; Nolan, Steven P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c434t-a131087452822985bfb0678d0c080f6a17c404f0932b48d6f829bedb80b6fb323</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Carbenes</topic><topic>Electronic properties</topic><topic>Excitation</topic><topic>Ligands</topic><topic>Metalorganic compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nelson, David J</creatorcontrib><creatorcontrib>Nolan, Steven P</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical Society reviews</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nelson, David J</au><au>Nolan, Steven P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Quantifying and understanding the electronic properties of N-heterocyclic carbenes</atitle><jtitle>Chemical Society reviews</jtitle><addtitle>Chem Soc Rev</addtitle><date>2013-01-01</date><risdate>2013</risdate><volume>42</volume><issue>16</issue><spage>6723</spage><epage>6753</epage><pages>6723-6753</pages><issn>0306-0012</issn><eissn>1460-4744</eissn><abstract>The use of
N
-heterocyclic carbenes (NHCs) in chemistry has developed rapidly over the past twenty years. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centres, and as organocatalysts able to mediate an exciting range of reactions. However, the sheer number of NHCs known in the literature can make the appropriate choice of NHC for a given application difficult. A number of metrics have been explored that allow the electronic properties of NHCs to be quantified and compared. In this review, we discuss these various metrics and what they can teach about the electronic properties of NHCs. Data for approximately three hundred NHCs are presented, obtained from a detailed survey of the literature.
The wide range of NHCs known in the literature can make choosing an NHC for a given application difficult. In this review, the electronic properties of NHCs are discussed, as well as the various methods by which they can be quantified. Data for
ca.
three hundred NHCs are provided.</abstract><cop>England</cop><pmid>23788114</pmid><doi>10.1039/c3cs60146c</doi><tpages>31</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Chemical Society reviews, 2013-01, Vol.42 (16), p.6723-6753 |
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| language | eng |
| recordid | cdi_proquest_miscellaneous_1786223902 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Carbenes Electronic properties Excitation Ligands Metalorganic compounds |
| title | Quantifying and understanding the electronic properties of N-heterocyclic carbenes |
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