Hydrogen Bonding Directed Reversal of 13 C NMR Chemical Shielding
The deshielding or downfield 13 C NMR chemical shift of amide carbonyl carbon upon H‐bonding is a widely observed phenomenon. This downfield shift is commonly used as a spectroscopic ruler for H‐bonding. However, the very first observation of an upfield 13 C NMR of thiocarbonyl carbon in thioamides...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2022-10, Vol.61 (41), p.e202207521-e202207521 |
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| container_issue | 41 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Jena, Subhrakant Routray, Chinmay Dutta, Juhi Biswal, Himansu S. |
| description | The deshielding or downfield
13
C NMR chemical shift of amide carbonyl carbon upon H‐bonding is a widely observed phenomenon. This downfield shift is commonly used as a spectroscopic ruler for H‐bonding. However, the very first observation of an upfield
13
C NMR of thiocarbonyl carbon in thioamides upon H‐bonding encouraged us to explore the physical origin of the reversal of
13
C NMR chemical shielding. Careful NMR analysis shows that sulfur and selenium‐centered H‐bonds (S/SeCHBs) induce a shielding effect on the
13
C
C=S(Se)
while changing from amides to thioamides or selenoamides. In addition, natural chemical shielding (NCS) analysis shows that the σ
11
and σ
22
components of the isotropic shielding tensor (σ) have a crucial role in this unusual shielding. |
| doi_str_mv | 10.1002/anie.202207521 |
| format | Article |
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13
C NMR chemical shift of amide carbonyl carbon upon H‐bonding is a widely observed phenomenon. This downfield shift is commonly used as a spectroscopic ruler for H‐bonding. However, the very first observation of an upfield
13
C NMR of thiocarbonyl carbon in thioamides upon H‐bonding encouraged us to explore the physical origin of the reversal of
13
C NMR chemical shielding. Careful NMR analysis shows that sulfur and selenium‐centered H‐bonds (S/SeCHBs) induce a shielding effect on the
13
C
C=S(Se)
while changing from amides to thioamides or selenoamides. In addition, natural chemical shielding (NCS) analysis shows that the σ
11
and σ
22
components of the isotropic shielding tensor (σ) have a crucial role in this unusual shielding.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202207521</identifier><language>eng</language><ispartof>Angewandte Chemie International Edition, 2022-10, Vol.61 (41), p.e202207521-e202207521</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1179-41d021554adc24316bcf80116b733f7a9d68fb664859a4720931d7a8149f1e513</citedby><cites>FETCH-LOGICAL-c1179-41d021554adc24316bcf80116b733f7a9d68fb664859a4720931d7a8149f1e513</cites><orcidid>0000-0003-0791-2259</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Jena, Subhrakant</creatorcontrib><creatorcontrib>Routray, Chinmay</creatorcontrib><creatorcontrib>Dutta, Juhi</creatorcontrib><creatorcontrib>Biswal, Himansu S.</creatorcontrib><title>Hydrogen Bonding Directed Reversal of 13 C NMR Chemical Shielding</title><title>Angewandte Chemie International Edition</title><description>The deshielding or downfield
13
C NMR chemical shift of amide carbonyl carbon upon H‐bonding is a widely observed phenomenon. This downfield shift is commonly used as a spectroscopic ruler for H‐bonding. However, the very first observation of an upfield
13
C NMR of thiocarbonyl carbon in thioamides upon H‐bonding encouraged us to explore the physical origin of the reversal of
13
C NMR chemical shielding. Careful NMR analysis shows that sulfur and selenium‐centered H‐bonds (S/SeCHBs) induce a shielding effect on the
13
C
C=S(Se)
while changing from amides to thioamides or selenoamides. In addition, natural chemical shielding (NCS) analysis shows that the σ
11
and σ
22
components of the isotropic shielding tensor (σ) have a crucial role in this unusual shielding.</description><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNo9kDtPwzAQgC0EEqWwMntkSfD5ETtjCY8iFZAKzJbrR2uUJsVukfrvSVXE9J1O393wIXQNpARC6K3poi8poZRIQeEEjWBAwaRkp8PMGSukEnCOLnL-GnylSDVCk-nepX7pO3zXdy52S3wfk7db7_Dc__iUTYv7gIHhBr--zHGz8utoh-X7Kvr2cHCJzoJps7_64xh9Pj58NNNi9vb03ExmhQWQdcHBEQpCcOMs5QyqhQ2KwEDJWJCmdpUKi6riStSGS0pqBk4aBbwO4AWwMbo5_t2k_nvn81avY7a-bU3n-13WVBKuJFSiHtTyqNrU55x80JsU1ybtNRB9aKUPrfR_K_YLH-9Zaw</recordid><startdate>20221010</startdate><enddate>20221010</enddate><creator>Jena, Subhrakant</creator><creator>Routray, Chinmay</creator><creator>Dutta, Juhi</creator><creator>Biswal, Himansu S.</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0791-2259</orcidid></search><sort><creationdate>20221010</creationdate><title>Hydrogen Bonding Directed Reversal of 13 C NMR Chemical Shielding</title><author>Jena, Subhrakant ; Routray, Chinmay ; Dutta, Juhi ; Biswal, Himansu S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1179-41d021554adc24316bcf80116b733f7a9d68fb664859a4720931d7a8149f1e513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jena, Subhrakant</creatorcontrib><creatorcontrib>Routray, Chinmay</creatorcontrib><creatorcontrib>Dutta, Juhi</creatorcontrib><creatorcontrib>Biswal, Himansu S.</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jena, Subhrakant</au><au>Routray, Chinmay</au><au>Dutta, Juhi</au><au>Biswal, Himansu S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrogen Bonding Directed Reversal of 13 C NMR Chemical Shielding</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2022-10-10</date><risdate>2022</risdate><volume>61</volume><issue>41</issue><spage>e202207521</spage><epage>e202207521</epage><pages>e202207521-e202207521</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The deshielding or downfield
13
C NMR chemical shift of amide carbonyl carbon upon H‐bonding is a widely observed phenomenon. This downfield shift is commonly used as a spectroscopic ruler for H‐bonding. However, the very first observation of an upfield
13
C NMR of thiocarbonyl carbon in thioamides upon H‐bonding encouraged us to explore the physical origin of the reversal of
13
C NMR chemical shielding. Careful NMR analysis shows that sulfur and selenium‐centered H‐bonds (S/SeCHBs) induce a shielding effect on the
13
C
C=S(Se)
while changing from amides to thioamides or selenoamides. In addition, natural chemical shielding (NCS) analysis shows that the σ
11
and σ
22
components of the isotropic shielding tensor (σ) have a crucial role in this unusual shielding.</abstract><doi>10.1002/anie.202207521</doi><orcidid>https://orcid.org/0000-0003-0791-2259</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| title | Hydrogen Bonding Directed Reversal of 13 C NMR Chemical Shielding |
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