Tautomerism in 1-phenylazo-4-naphthols: experimental results vs quantum-chemical predictions
- Antonov, Liudmil Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
- Kurteva, Vanya Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
- Crochet, Aurélien University of Fribourg, Department of Chemistry, Fribourg, Switzerland
- Mirolo, Laurent University of Fribourg, Department of Chemistry, Fribourg, Switzerland
- Fromm, Katharina M. University of Fribourg, Department of Chemistry, Fribourg, Switzerland
- Angelova, Silvia Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
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11.06.2011
Published in:
- Dyes and Pigments. - 2012, vol. 92, no. 1, p. 714–723
English
The reliability in the description of the tautomerism of 1-phenylazo-4-naphthol by using of HF and MP2 ab initio levels of theory and DFT methods with variety of pure GGA (OLYP), hybrid (B3LYP and B3PW91), long range corrected (LC-BLYP) and double-hybrid (B2PLYP and mPW2PLYP) functionals with large number of basis sets was estimated. In this evaluation three criteria were used: reproduction of the bond lengths in the structures of the individual tautomers, description of the non-planarity of the enol tautomer and prediction of the position of the tautomeric equilibrium (∆G value) at 298 K. The results show that in substantial number of cases HF reasonably covers all requirements. The tested pure (OLYP) and hybrid functionals (B3LYP and B3PW91) fail in the prediction of the position of the equilibrium independent on the basis set. The situation is slightly better at the long range corrected functional (LC- BLYP), which give predominance of the enol tautomer at 6-31+G** and D95++**. The double hybrid functionals give very good description with D95++** basis set, but at substantial computational costs.
- Faculty
- Faculté des sciences et de médecine
- Department
- Département de Chimie
- Language
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- English
- Classification
- Chemistry
- License
- License undefined
- Identifiers
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- RERO DOC 29022
- DOI 10.1016/j.dyepig.2011.06.026
- Persistent URL
- https://folia.unifr.ch/unifr/documents/302383
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