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Pregled bibliografske jedinice broj: 1061238

Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents


Leko, Katarina; Hanževački, Marko; Brkljača, Zlatko; Pičuljan, Katarina; Ribić, Rosana; Požar, Josip
Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents // Chemistry : a European journal, 26 (2020), 23; 5208-5219 doi:10.1002/chem.202000282 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1061238 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents

Autori
Leko, Katarina ; Hanževački, Marko ; Brkljača, Zlatko ; Pičuljan, Katarina ; Ribić, Rosana ; Požar, Josip

Izvornik
Chemistry : a European journal (0947-6539) 26 (2020), 23; 5208-5219

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

Ključne riječi
hydrophobic effect ; solvophobic effect ; adamantane ; β–cyclodextrin ; complexation thermodynamics

Sažetak
The effects of solvent and temperature on the complexation of adamantyl mannoside with β‐ cyclodextrin and 6‐O‐monotosyl‐6‐deoxy‐β‐ cyclodextrin were explored experimentally and by means of molecular dynamics simulations. Efficient binding was observed only in hydrogen‐bonded solvents, which indicated solvophobically driven complexation. The stability of the inclusion complex was considerably higher in aqueous media. A pronounced temperature dependence of ΔrH○ and ΔrS○, resulting in perfect enthalpy–entropy compensation, was observed in water. The complexation thermodynamics was in line with classical rationale for the hydrophobic effect at lower temperatures and the nonclassical explanation at higher temperatures. This finding linked cyclodextrin complexation thermodynamics with insights regarding the effect of temperature on the hydration water structure. The complexation enthalpies and entropies were weakly dependent on temperature in organic media. The signs of ΔrH○ and ΔrS○ were in accordance with the nonclassical hydrophobic (solvophobic) effect. The structures of the optimized product corresponded to those deduced spectroscopically, and the calculated and experimentally obtained values of ΔrG○ were in very good agreement. This investigation clearly demonstrated that solvophobically driven formation of cyclodextrin complexes could be anticipated in structured solvents in general. However, unlike in water, adamantane and the host cavity behaved solely as structure breakers in the organic media explored so far.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
HRZZ-IP-2019-04-9560 - Koordinacijske reakcije makrocikličkih liganada u otopini (MacroSol) (Tomišić, Vladislav, HRZZ - 2019-04) ( POIROT)

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

Poveznice na cjeloviti tekst rada:

doi chemistry-europe.onlinelibrary.wiley.com doi.org

Citiraj ovu publikaciju:

Leko, Katarina; Hanževački, Marko; Brkljača, Zlatko; Pičuljan, Katarina; Ribić, Rosana; Požar, Josip
Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents // Chemistry : a European journal, 26 (2020), 23; 5208-5219 doi:10.1002/chem.202000282 (međunarodna recenzija, članak, znanstveni)
Leko, K., Hanževački, M., Brkljača, Z., Pičuljan, K., Ribić, R. & Požar, J. (2020) Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents. Chemistry : a European journal, 26 (23), 5208-5219 doi:10.1002/chem.202000282.
@article{article, author = {Leko, Katarina and Han\v{z}eva\v{c}ki, Marko and Brklja\v{c}a, Zlatko and Pi\v{c}uljan, Katarina and Ribi\'{c}, Rosana and Po\v{z}ar, Josip}, year = {2020}, pages = {5208-5219}, DOI = {10.1002/chem.202000282}, keywords = {hydrophobic effect, solvophobic effect, adamantane, β–cyclodextrin, complexation thermodynamics}, journal = {Chemistry : a European journal}, doi = {10.1002/chem.202000282}, volume = {26}, number = {23}, issn = {0947-6539}, title = {Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents}, keyword = {hydrophobic effect, solvophobic effect, adamantane, β–cyclodextrin, complexation thermodynamics} }
@article{article, author = {Leko, Katarina and Han\v{z}eva\v{c}ki, Marko and Brklja\v{c}a, Zlatko and Pi\v{c}uljan, Katarina and Ribi\'{c}, Rosana and Po\v{z}ar, Josip}, year = {2020}, pages = {5208-5219}, DOI = {10.1002/chem.202000282}, keywords = {hydrophobic effect, solvophobic effect, adamantane, β–cyclodextrin, complexation thermodynamics}, journal = {Chemistry : a European journal}, doi = {10.1002/chem.202000282}, volume = {26}, number = {23}, issn = {0947-6539}, title = {Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents}, keyword = {hydrophobic effect, solvophobic effect, adamantane, β–cyclodextrin, complexation thermodynamics} }

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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