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Pregled bibliografske jedinice broj: 626942

Časopis

Autori: Veljković, Jelena; Antol, Ivana; Basarić, Nikola; Smrečki, Vilko; Molčanov, Krešimir; Müller, Norbert; Mlinarić-Majerski, Kata
Naslov: Atropisomerism in 1-(2-Adamantyl)naphthalene Derivatives
Izvornik: Journal of molecular structure (0022-2860) 1046 (2013); 101-109
Vrsta rada: članak
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.
Projekt / tema: 02.05/25, 098-0982933-2911, 098-1191344-2943, 098-0982929-2917
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://authors.elsevier.com/sd/article/S0022286013003232
http://dx.doi.org/10.1016/j.molstruc.2013.04.027
Broj citata:
Altmetric:
DOI: 10.1016/j.molstruc.2013.04.027
URL cjelovitog teksta:
Google Scholar: Atropisomerism in 1-(2-Adamantyl)naphthalene Derivatives
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 26. Tra. 2013. u 10:59 sati



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