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Pregled bibliografske jedinice broj: 607101

Synthesis, structure and tautomerism of two benzothiazolyl azo derivatives of 2-naphthol: A crystallographic, NMR and computational study


Racane, Livio; Mihalić, Zlatko; Cerić, Helena; Popović, Jasminka; Tralić-Kulenović, Vesna
Synthesis, structure and tautomerism of two benzothiazolyl azo derivatives of 2-naphthol: A crystallographic, NMR and computational study // Dyes and pigments, 96 (2013), 3; 672-678 doi:10.1016/j.dyepig.2012.10.009 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis, structure and tautomerism of two benzothiazolyl azo derivatives of 2-naphthol: A crystallographic, NMR and computational study

Autori
Racane, Livio ; Mihalić, Zlatko ; Cerić, Helena ; Popović, Jasminka ; Tralić-Kulenović, Vesna

Izvornik
Dyes and pigments (0143-7208) 96 (2013), 3; 672-678

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Azo dyes; synthesis; crystal structure; DFT-calculations; azo-hydrazone tautomerism; NMR spectroscopy

Sažetak
The efficient synthesis, 1H and 13C NMR characterization, crystal and molecular structure, DFT calculations of 6-[(2-hydroxy-1-naphthyl)diazenyl]-2-methylbenzothiazole, as well as DFT calculations of 6-[(2-hydroxy-1-naphthyl)diazenyl benzothiazole, are reported. Single-crystal X-ray diffraction data show that crystals of the azo dye derived from 2-methylbenzothiazole is principally composed of the hydrazone form. 2D NMR techniques (COSY, HMQC and HMBC) were used to assign 1H and 13C chemical shifts for each azo dye in DMSO and CHCl3 solution. Azoehydrazone tautomerism of the dyes was investigated jointly by 13C NMR and DFT calculations. All three approaches show that in solution the equilibrium is only slightly shifted towards the hydrazone form. The very good agreement between the three differently obtained equilibrium constants suggest M06-2X/6-311þG(d, p)-SMD as the level of theory of choice for quantum-mechanical calculations of these and similar compounds in solution.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Tekstilna tehnologija



POVEZANOST RADA


Projekt / tema
117-0000000-3283 - Istraživanje novih višenamjenskih bojila i optičkih bjelila (Livio Racane, )
119-1191342-1339 - Molekulsko modeliranje strukture i reaktivnosti organskih spojeva (Zlatko Mihalić, )

Ustanove
Tekstilno-tehnološki fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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