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Identification of tautomeric intermediates of a novel thiazolylazonaphthol dye - A density functional theory study
Bohdan Khmelnytsky Natl Univ, Dept Chem & Nanomat Sci, UA-18031 Cherkassy, Ukraine..
Bohdan Khmelnytsky Natl Univ, Dept Chem & Nanomat Sci, UA-18031 Cherkassy, Ukraine..
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology. Bohdan Khmelnytsky Natl Univ, Dept Chem & Nanomat Sci, UA-18031 Cherkassy, Ukraine.ORCID iD: 0000-0002-0716-3385
Bohdan Khmelnytsky Natl Univ, Dept Chem & Nanomat Sci, UA-18031 Cherkassy, Ukraine.
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2018 (English)In: Spectrochimica Acta Part A - Molecular and Biomolecular Spectroscopy, ISSN 1386-1425, E-ISSN 1873-3557, Vol. 203, p. 324-332Article in journal (Refereed) Published
Abstract [en]

The recently synthesized thiazolylazo dye, 1-(5-benzy1-1,3-thiazol-2-yl)diazenyllnaphthalene-2-ol called shortly BnTAN, is studied by density functional theory (DFT) in three tautomeric forms in order to explain the available H-1 NMR, UV-Vis and FTIR spectra. An experimentally observed IR band at 1678 cm(-1), assigned to the C=O bond stretching vibration, supports the notion that BnTAN retains in the less stable keto-form even in the solid state due to an ultrafast single-coordinate intramolecular proton transfer. This finding is also in a good agreement with an X-ray crystallography analysis which indicates an intermediate position of the proton between the OH and -N=N-groups. Calculations also show that some experimentally observed H-I NMR signals could be considered as being averaged values between theoretically calculated chemical shifts for the corresponding protons in the keto- and enol-tautomers. At the same time the UV-Vis spectra are almost insensitive to the tautomerization processes as the main single band absorption at 500 nm is present in all tautomers according to our TD DFT simulations. The minor differences in spectral features of the long-wavelength visible region are also noted and discussed with respect to the manifestation of the less stable tautomer form.

Place, publisher, year, edition, pages
Pergamon Press, 2018. Vol. 203, p. 324-332
Keywords [en]
Tautomers, FTIR spectra, UV-vis spectra, NMR spectra, DFT calculations
National Category
Theoretical Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-232582DOI: 10.1016/j.saa.2018.05.096ISI: 000437816000040PubMedID: 29879648Scopus ID: 2-s2.0-85047933840OAI: oai:DiVA.org:kth-232582DiVA, id: diva2:1235738
Funder
Carl Tryggers foundation , CTS 17:514Stiftelsen Olle Engkvist Byggmästare, 189-0223
Note

QC 20180727

Available from: 2018-07-27 Created: 2018-07-27 Last updated: 2018-07-27Bibliographically approved

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Baryshnikov, Gleb V.Minaev, Boris F.Ågren, Hans

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