Pregled bibliografske jedinice broj: 327498
Nondegenerate equilibrium in (2-propyl)cycloalkyl cations. Comparison of (2-propyl)cyclopentyl and (2-propyl)cyclohexyl cation using 13C NMR spectroscopy, equilibrium isotope effects and quantum chemical calculations
Nondegenerate equilibrium in (2-propyl)cycloalkyl cations. Comparison of (2-propyl)cyclopentyl and (2-propyl)cyclohexyl cation using 13C NMR spectroscopy, equilibrium isotope effects and quantum chemical calculations // Journal of Chemical Society - Perkin Transactions II, 2002 (2002), 1; 106-113 doi:10.1039/b107756b (međunarodna recenzija, članak, znanstveni)
CROSBI ID: 327498 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
Nondegenerate equilibrium in (2-propyl)cycloalkyl cations. Comparison of (2-propyl)cyclopentyl and (2-propyl)cyclohexyl cation using 13C NMR spectroscopy, equilibrium isotope effects and quantum chemical calculations
Autori
Siehl, Hans-Ullrich ; Vrček, Valerije ; Kronja, Olga
Izvornik
Journal of Chemical Society - Perkin Transactions II (1472-779X) 2002
(2002), 1;
106-113
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
NMR spectroscopy; carbocation; rearrangement
Sažetak
Tertiary (2-propyl)cyclopentyl and (2-propyl)cyclohexyl carbocations were investigated by 13C NMR spectroscopy in superacid solution. Both ions undergo fast nondegenerate 1, 2-hydride shifts to the corresponding 2-cycloalkyl-2-propyl cations. The direction of these equilibria depends on the size of the ring. The more stable isomer of the (2-propyl)cyclopentyl cation has the formal positive charge at the endocyclic carbon atom, while the more stable isomer of the (2-propyl)cyclohexyl cation has the formal charge at the exocyclic carbon atom. The dynamic NMR results were confirmed by NMR spectroscopic measurement of the equilibrium isotope effects and rationalized by quantum chemical calculations.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
Citiraj ovu publikaciju:
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
