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Atropisomerism in 1-(2-Adamantyl)naphthalene Derivatives


Veljković, Jelena; Antol, Ivana; Basarić, Nikola; Smrečki, Vilko; Molčanov, Krešimir; Müller, Norbert; Mlinarić-Majerski, Kata
Atropisomerism in 1-(2-Adamantyl)naphthalene Derivatives // Journal of molecular structure, 1046 (2013), 101-109 doi:10.1016/j.molstruc.2013.04.027 (međunarodna recenzija, članak, znanstveni)


Naslov
Atropisomerism in 1-(2-Adamantyl)naphthalene Derivatives

Autori
Veljković, Jelena ; Antol, Ivana ; Basarić, Nikola ; Smrečki, Vilko ; Molčanov, Krešimir ; Müller, Norbert ; Mlinarić-Majerski, Kata

Izvornik
Journal of molecular structure (0022-2860) 1046 (2013); 101-109

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

Ključne riječi
Adamantanes; Naphthalenes; Atropisomers; DFT calculations; Dynamic NMR

Sažetak
Two new adamantylnaphthalene derivatives 1-(2-hydroxy-2-adamantyl)-4-methoxynaphthalene (5) and 1-(2-hydroxy-2-adamantyl)-5-methoxynaphthalene (6) were synthesized and characterized by NMR spectroscopy. In addition, 5 was characterized by single crystal X-ray structural analysis and DFT calculations. For both derivatives, 5 and 6, dynamic NMR of diastereotopic spins revealed atropisomerism due to hindered rotation around the C-C bond between the adamantyl and the naphthyl moieties, giving rise to intermediate conformational exchange on the NMR timescale at room temperature. Upon decrease of the temperature to 223 K the existence of two enantiomerically related conformers in slow exchange was observed. The free energy of activation for the conformer exchange calculated using the coalescence temperature method amounts to 56.4 ± 0.3 kJ mol-1 for both derivatives. The experimental findings are corroborated by DFT calculations. The calculated NMR chemical shifts and the energy of activation for the conformer exchange are in excellent agreement with the measured values.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
02.05/25
098-0982929-2917 - Spektroskopija NMR i modeliranje bioaktivnih molekula (Dejan Plavšić, )
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )
098-1191344-2943 - Protein-ligand međudjelovanja na atomnoj razini (Marija Luić, )

Ustanove
Institut "Ruđer Bošković", 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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