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A theoretical study of dynamic processes observed in trimethylsilyl-1H-pyrazoles: prototropy and silylotropy
The 1 H, 13 C, 15 N and 29 Si chemical shifts of three trimethylsilyl-1 H -pyrazoles were calculated and compared with literature results; the calculations were carried out at the GIAO/B3LYP/6–311 + + G(d,p) level resulting in a very good agreement that allows to predict with confidence the missing...
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| Published in: | Theoretical chemistry accounts 2022-12, Vol.141 (12), Article 78 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| container_issue | 12 |
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| container_title | Theoretical chemistry accounts |
| container_volume | 141 |
| creator | Claramunt, Rosa M. Elguero, José Alkorta, Ibon |
| description | The
1
H,
13
C,
15
N and
29
Si chemical shifts of three trimethylsilyl-1
H
-pyrazoles were calculated and compared with literature results; the calculations were carried out at the GIAO/B3LYP/6–311 + + G(d,p) level resulting in a very good agreement that allows to predict with confidence the missing experimental values. The prototropic barrier of 4-trimethylsilyl-1
H
-pyrazole (
1
) as well as the silylotropic barriers of 1-trimethylsilyl-1
H
-pyrazole (
2
) and 1-trimethylsilyl-4-methyl-1
H
-pyrazole (
3
) were also calculated and the mechanism was established, the accordance with the experimental values being satisfactory. |
| doi_str_mv | 10.1007/s00214-022-02936-z |
| format | article |
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1
H,
13
C,
15
N and
29
Si chemical shifts of three trimethylsilyl-1
H
-pyrazoles were calculated and compared with literature results; the calculations were carried out at the GIAO/B3LYP/6–311 + + G(d,p) level resulting in a very good agreement that allows to predict with confidence the missing experimental values. The prototropic barrier of 4-trimethylsilyl-1
H
-pyrazole (
1
) as well as the silylotropic barriers of 1-trimethylsilyl-1
H
-pyrazole (
2
) and 1-trimethylsilyl-4-methyl-1
H
-pyrazole (
3
) were also calculated and the mechanism was established, the accordance with the experimental values being satisfactory.</description><identifier>ISSN: 1432-881X</identifier><identifier>EISSN: 1432-2234</identifier><identifier>DOI: 10.1007/s00214-022-02936-z</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Atomic/Molecular Structure and Spectra ; Chemistry ; Chemistry and Materials Science ; Inorganic Chemistry ; Mathematical analysis ; Organic Chemistry ; Physical Chemistry ; Pyrazole ; Theoretical and Computational Chemistry</subject><ispartof>Theoretical chemistry accounts, 2022-12, Vol.141 (12), Article 78</ispartof><rights>The Author(s) 2022</rights><rights>The Author(s) 2022. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c314t-99ee1af631e6069d6108df5a947917729f9cf1a8867028aa1af9c05c636ecc0a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Claramunt, Rosa M.</creatorcontrib><creatorcontrib>Elguero, José</creatorcontrib><creatorcontrib>Alkorta, Ibon</creatorcontrib><title>A theoretical study of dynamic processes observed in trimethylsilyl-1H-pyrazoles: prototropy and silylotropy</title><title>Theoretical chemistry accounts</title><addtitle>Theor Chem Acc</addtitle><description>The
1
H,
13
C,
15
N and
29
Si chemical shifts of three trimethylsilyl-1
H
-pyrazoles were calculated and compared with literature results; the calculations were carried out at the GIAO/B3LYP/6–311 + + G(d,p) level resulting in a very good agreement that allows to predict with confidence the missing experimental values. The prototropic barrier of 4-trimethylsilyl-1
H
-pyrazole (
1
) as well as the silylotropic barriers of 1-trimethylsilyl-1
H
-pyrazole (
2
) and 1-trimethylsilyl-4-methyl-1
H
-pyrazole (
3
) were also calculated and the mechanism was established, the accordance with the experimental values being satisfactory.</description><subject>Atomic/Molecular Structure and Spectra</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Inorganic Chemistry</subject><subject>Mathematical analysis</subject><subject>Organic Chemistry</subject><subject>Physical Chemistry</subject><subject>Pyrazole</subject><subject>Theoretical and Computational Chemistry</subject><issn>1432-881X</issn><issn>1432-2234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LAzEQhoMoWKt_wFPAczQfu8nGWylqhYIXBW8hZmftlu2mJqmw_fWmXcGbh2Fm4Hnn40XomtFbRqm6i5RyVhDKeQ4tJNmfoAkrBCeci-L0t64q9n6OLmJc08zzUk1QN8NpBT5Aap3tcEy7esC-wfXQ203r8DZ4BzFCxP4jQviGGrc9TqHdQFoNXWy7oSNsQbZDsHvfQbw_SJJPwW8HbPsaH5Gxv0Rnje0iXP3mKXp7fHidL8jy5el5PlsSJ1iRiNYAzDZSMJBU6loyWtVNaXWhNFOK60a7htmqkoryytrMakdLJ4UE56gVU3Qzzs2nfO0gJrP2u9DnlYYroZQoeckyxUfKBR9jgMZs81s2DIZRc3DVjK6abJU5umr2WSRGUcxw_wnhb_Q_qh9cLn1r</recordid><startdate>20221201</startdate><enddate>20221201</enddate><creator>Claramunt, Rosa M.</creator><creator>Elguero, José</creator><creator>Alkorta, Ibon</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>C6C</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20221201</creationdate><title>A theoretical study of dynamic processes observed in trimethylsilyl-1H-pyrazoles: prototropy and silylotropy</title><author>Claramunt, Rosa M. ; Elguero, José ; Alkorta, Ibon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c314t-99ee1af631e6069d6108df5a947917729f9cf1a8867028aa1af9c05c636ecc0a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Atomic/Molecular Structure and Spectra</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Inorganic Chemistry</topic><topic>Mathematical analysis</topic><topic>Organic Chemistry</topic><topic>Physical Chemistry</topic><topic>Pyrazole</topic><topic>Theoretical and Computational Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Claramunt, Rosa M.</creatorcontrib><creatorcontrib>Elguero, José</creatorcontrib><creatorcontrib>Alkorta, Ibon</creatorcontrib><collection>SpringerOpen</collection><collection>CrossRef</collection><jtitle>Theoretical chemistry accounts</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Claramunt, Rosa M.</au><au>Elguero, José</au><au>Alkorta, Ibon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A theoretical study of dynamic processes observed in trimethylsilyl-1H-pyrazoles: prototropy and silylotropy</atitle><jtitle>Theoretical chemistry accounts</jtitle><stitle>Theor Chem Acc</stitle><date>2022-12-01</date><risdate>2022</risdate><volume>141</volume><issue>12</issue><artnum>78</artnum><issn>1432-881X</issn><eissn>1432-2234</eissn><abstract>The
1
H,
13
C,
15
N and
29
Si chemical shifts of three trimethylsilyl-1
H
-pyrazoles were calculated and compared with literature results; the calculations were carried out at the GIAO/B3LYP/6–311 + + G(d,p) level resulting in a very good agreement that allows to predict with confidence the missing experimental values. The prototropic barrier of 4-trimethylsilyl-1
H
-pyrazole (
1
) as well as the silylotropic barriers of 1-trimethylsilyl-1
H
-pyrazole (
2
) and 1-trimethylsilyl-4-methyl-1
H
-pyrazole (
3
) were also calculated and the mechanism was established, the accordance with the experimental values being satisfactory.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s00214-022-02936-z</doi><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 1432-881X |
| ispartof | Theoretical chemistry accounts, 2022-12, Vol.141 (12), Article 78 |
| issn | 1432-881X 1432-2234 |
| language | eng |
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| subjects | Atomic/Molecular Structure and Spectra Chemistry Chemistry and Materials Science Inorganic Chemistry Mathematical analysis Organic Chemistry Physical Chemistry Pyrazole Theoretical and Computational Chemistry |
| title | A theoretical study of dynamic processes observed in trimethylsilyl-1H-pyrazoles: prototropy and silylotropy |
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