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Pregled bibliografske jedinice broj: 626942

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)

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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

Projekti:
02.05/25 - Fotokemija policikličkih molekula: od istraživanja mehanizama reakcije do novih lijekova i medicinskih primjena (Basarić, Nikola, HRZZ ) ( CroRIS)
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Majerski, Kata, MZOS ) ( CroRIS)
098-0982929-2917 - Spektroskopija NMR i modeliranje bioaktivnih molekula (Plavšić, Dejan, MZOS ) ( CroRIS)
098-1191344-2943 - Protein-ligand međudjelovanja na atomnoj razini (Luić, Marija, MZOS ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Ivana Antol (autor)

Avatar Url Kata Majerski (autor)

Avatar Url Jelena Veljković (autor)

Avatar Url Krešimir Molčanov (autor)

Avatar Url Vilko Smrečki (autor)

Avatar Url Nikola Basarić (autor)

Poveznice na cjeloviti tekst rada:

doi authors.elsevier.com dx.doi.org

Citiraj ovu publikaciju:

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)
Veljković, J., Antol, I., Basarić, N., Smrečki, V., Molčanov, K., Müller, N. & Mlinarić-Majerski, K. (2013) Atropisomerism in 1-(2-Adamantyl)naphthalene Derivatives. Journal of molecular structure, 1046, 101-109 doi:10.1016/j.molstruc.2013.04.027.
@article{article, author = {Veljkovi\'{c}, Jelena and Antol, Ivana and Basari\'{c}, Nikola and Smre\v{c}ki, Vilko and Mol\v{c}anov, Kre\v{s}imir and M\"{u}ller, Norbert and Mlinari\'{c}-Majerski, Kata}, year = {2013}, pages = {101-109}, DOI = {10.1016/j.molstruc.2013.04.027}, keywords = {Adamantanes, Naphthalenes, Atropisomers, DFT calculations, Dynamic NMR}, journal = {Journal of molecular structure}, doi = {10.1016/j.molstruc.2013.04.027}, volume = {1046}, issn = {0022-2860}, title = {Atropisomerism in 1-(2-Adamantyl)naphthalene Derivatives}, keyword = {Adamantanes, Naphthalenes, Atropisomers, DFT calculations, Dynamic NMR} }
@article{article, author = {Veljkovi\'{c}, Jelena and Antol, Ivana and Basari\'{c}, Nikola and Smre\v{c}ki, Vilko and Mol\v{c}anov, Kre\v{s}imir and M\"{u}ller, Norbert and Mlinari\'{c}-Majerski, Kata}, year = {2013}, pages = {101-109}, DOI = {10.1016/j.molstruc.2013.04.027}, keywords = {Adamantanes, Naphthalenes, Atropisomers, DFT calculations, Dynamic NMR}, journal = {Journal of molecular structure}, doi = {10.1016/j.molstruc.2013.04.027}, volume = {1046}, issn = {0022-2860}, title = {Atropisomerism in 1-(2-Adamantyl)naphthalene Derivatives}, keyword = {Adamantanes, Naphthalenes, Atropisomers, DFT calculations, Dynamic NMR} }

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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