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Journal

2006 | 4 | 3 | 523-532

Article title

The influence of solvent molecules on NMR spectrum of barbituric acid in the DMSO solution

Content

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Languages of publication

EN

Abstracts

EN
This work shows the modification of barbituric acid (BA) chemical shifts by dimethylsulphoxide (DMSO) molecules. The discussed changes are caused by creation of the H-bonded associates formed by barbituric acid with DMSO in solution. Free molecule of barbituric acid, the cluster of BA with two DMSO molecules and two different clusters of BA with four DMSO units are taken into consideration. The chemical shifts of these systems have been calculated and the obtained results have been compared with experimental data. Theoretical calculations predict a significant downfield shift for imino protons of barbituric acid involved in intermolecular-N-H...DMSO hydrogen bonds. The influence of the solvent molecules on other nuclei chemical shifts, especially protons of barbituric acid methylene group, is also reported.The calculations have involved Hartree-Fock and several Density Functional Theory methods. All methods correctly describe experimental 1H and 13C NMR spectra of barbituric acid. The best consistence between experiment and theory is observed for the BLYP functional. Four approximations of magnetic properties calculations embedded in the Gaussian’98 package have been tested. The results of the performed calculations indicate that from a practical point of view the GIAO method should be preferred.

Publisher

Journal

Year

Volume

4

Issue

3

Pages

523-532

Physical description

Dates

published
1 - 9 - 2006
online
1 - 9 - 2006

Contributors

  • Department of Organic Chemistry, Medical College, Jagiellonian University, 30-688, Kraków, Poland
  • Department of Chemical Physics, Faculty of Chemistry, Jagiellonian University, 30-060, Kraków, Poland

References

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Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-006-0019-z
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