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Pregled bibliografske jedinice broj: 705739

Supramolecular stabilization of metastable tautomers in solution and solid state


Juribašić, Marina; Bregović, Nikola; Stilinović, Vladimir; Tomišić, Vladislav; Cindrić, Marina; Šket, Primož; Plavec, Janez; Rubčić, Mirta; Užarević, Krunoslav
Supramolecular stabilization of metastable tautomers in solution and solid state // Chemistry : a European journal, 20 (2014), 52; 17333-17345 doi:10.1002/chem.201403543 (međunarodna recenzija, članak, znanstveni)


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Naslov
Supramolecular stabilization of metastable tautomers in solution and solid state

Autori
Juribašić, Marina ; Bregović, Nikola ; Stilinović, Vladimir ; Tomišić, Vladislav ; Cindrić, Marina ; Šket, Primož ; Plavec, Janez ; Rubčić, Mirta ; Užarević, Krunoslav

Izvornik
Chemistry : a European journal (0947-6539) 20 (2014), 52; 17333-17345

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

Ključne riječi
tautomerism; Schiff base; keto-enol; supramolecular stabilization; metastable tautomers

Sažetak
This work presents a successful application of recently reported supramolecular strategy for stabilization of metastable tautomers in cocrystals to monocomponent non-heterocyclic tautomeric solids. The quantum-chemical computations and solution studies show that the investigated Schiff base molecule, derived from 3-methoxysalycilaldehyde and 2-amino-3-hydroxypyridine (ap), is far more stable as the enol tautomer. In the solid state however, in all three obtained polymorphic forms it existed solely as the keto tautomer, in each case stabilized by unexpected hydrogen bonding pattern. The computations have shown that hydrogen bonding of investigated Schiff base with the suitable molecules shifts the tautomeric equilibrium to the less stable keto form. The extremes to which supramolecular stabilization can lead are demonstrated by the two polymorphs of molecular complexes of Schiff base with ap. The molecules of both constituents of molecular complexes are present as metastable tautomers (keto anion and protonated pyridine, respectively), stabilizing each other via a very strong hydrogen bond. All obtained solid forms proved stable on various solid-state and solvent mediated methods used to establish their relative thermodynamic stabilities and possible interconversion conditions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982915-2950 - Dizajn, sinteza i svojstva organskih liganada i njihovih metalnih kompleksa (Manda Ćurić, )
119-1191342-1082 - Novi kompleksni spojevi i materijali-kemijski i biološki katalizatori (Marina Cindrić, )
119-1191342-2960 - Elektroliti i koordinacijske reakcije u otopini (Vladislav Tomišić, )
119-1193079-3069 - Novi organski i koordinacijski spojevi - sinteza i suodnos struktura-svojstvo (Branko Kaitner, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Citiraj ovu publikaciju

Juribašić, Marina; Bregović, Nikola; Stilinović, Vladimir; Tomišić, Vladislav; Cindrić, Marina; Šket, Primož; Plavec, Janez; Rubčić, Mirta; Užarević, Krunoslav
Supramolecular stabilization of metastable tautomers in solution and solid state // Chemistry : a European journal, 20 (2014), 52; 17333-17345 doi:10.1002/chem.201403543 (međunarodna recenzija, članak, znanstveni)
Juribašić, M., Bregović, N., Stilinović, V., Tomišić, V., Cindrić, M., Šket, P., Plavec, J., Rubčić, M. & Užarević, K. (2014) Supramolecular stabilization of metastable tautomers in solution and solid state. Chemistry : a European journal, 20 (52), 17333-17345 doi:10.1002/chem.201403543.
@article{article, year = {2014}, pages = {17333-17345}, DOI = {10.1002/chem.201403543}, keywords = {tautomerism, Schiff base, keto-enol, supramolecular stabilization, metastable tautomers}, journal = {Chemistry : a European journal}, doi = {10.1002/chem.201403543}, volume = {20}, number = {52}, issn = {0947-6539}, title = {Supramolecular stabilization of metastable tautomers in solution and solid state}, keyword = {tautomerism, Schiff base, keto-enol, supramolecular stabilization, metastable tautomers} }

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
  • MEDLINE


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