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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Bibliographic Details
Published in:Theoretical chemistry accounts 2022-12, Vol.141 (12), Article 78
Main Authors: Claramunt, Rosa M., Elguero, José, Alkorta, Ibon
Format: Article
Language:English
Subjects:
Atomic/Molecular Structure and Spectra
Chemistry
Chemistry and Materials Science
Inorganic Chemistry
Mathematical analysis
Organic Chemistry
Physical Chemistry
Pyrazole
Theoretical and Computational Chemistry
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Summary: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.
ISSN:1432-881X
1432-2234
DOI:10.1007/s00214-022-02936-z