Naslov
Chiroptical and conformational properties of (R)-1-phenylethylamine derivatives of persubstituted benzene

Autori
Kontrec, Darko ; Vinković, Vladimir ; Lesac, Andreja ; Šunjić, Vitomir ; Hollosi, Miklos

Izvornik
Tetrahedron : asymmetry (0957-4166) 10 (1999), 10; 1935-1945

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

Ključne riječi
chiral derivatives ; chiroptical and conformational properties ; persubstituted benzene

Sažetak
Chiral derivatives of 2, 4, 5, 6-tetrachloro-1, 3-dicyanobenzene 1 with one, two and three (R)-1-phenylethylamino ((R)-PEA) units 2–4 are prepared and their chiroptical and conformational properties discussed on the bases of the UV/CD, NMR and MM2 data. High polarity of the persubstituted benzene ring leads to peculiar UV and IR spectra of achiral model compounds 5–7, whereas relatively rigid conformations of the chiral analogues 2–4 are reflected in the CD spectra. Strong exciton coupling (EC) appears in the CD spectrum of pseudo-C3-symmetric 4 ; this type of interaction seems not to be present in the C1-symmetric 2 and C2-symmetric 3. The absence of a molecular cleft in the chiral structures 2–4 could explain their inability to recognise the enantiomers of some racemates in the NMR experiment.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA