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Pregled bibliografske jedinice broj: 322842

1, n′ -Disubstituted ferrocenoyl amino acids and dipeptides: Conformational analysis by CD spectroscopy, X-ray crystallography, and DFT calculations


Kirin, Srećko I.; Schatzschneider, Ulrich; De Hatten, Xaveir; Weyhermüller, Thomas; Metzler-Nolte, Nils
1, n′ -Disubstituted ferrocenoyl amino acids and dipeptides: Conformational analysis by CD spectroscopy, X-ray crystallography, and DFT calculations // Journal of Organometallic Chemistry, 691 (2006), 16; 3451-3457 (međunarodna recenzija, članak, znanstveni)


Naslov
1, n′ -Disubstituted ferrocenoyl amino acids and dipeptides: Conformational analysis by CD spectroscopy, X-ray crystallography, and DFT calculations

Autori
Kirin, Srećko I. ; Schatzschneider, Ulrich ; De Hatten, Xaveir ; Weyhermüller, Thomas ; Metzler-Nolte, Nils

Izvornik
Journal of Organometallic Chemistry (0022-328X) 691 (2006), 16; 3451-3457

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

Ključne riječi
Amino acids; bioconjugates; bioorganometallic chemistry; DFT calculations; ferrocene; hydrogen bonding

Sažetak
An experimental and computational study on the conformational preference of 1, n′ -disubstituted ferrocenoyl amino acids and dipeptides is presented. Only l-amino acids were used for the synthesis of Fe[C5H4-CO-Met-Met-OMe]2 (4), but according to the X-ray structure a 4:1 mixture of l, d, M, d, l and l, d, M, l, l isomers is obtained (l describes amino acid chirality and M the helical chirality of the ferrocene core). This result is in agreement with IR and CD solution phase data and can be explained with a racemization by 1 M NaOH during the synthesis. In order to determine the relative stabilities of the different conformations, DFT calculations on model compounds Fe[C5H4-CO-Gly-NH2]2 (5) and Fe[C5H4-CO-Ala-OMe]2 (6) were performed using the B3LYP/LanL2DZ method with ECPs on the heavy atoms. Conformers 5A– 5C with different hydrogen bond patterns have significantly different stabilities with a stabilization by about 30 kJ mol− 1 per hydrogen bond. The “ Herrick conformation” 5A with two hydrogen bonds is the most stable in the gas phase, in accordance with the solution and solid phase data. In contrast, only small energetic differences (less than 10 kJ mol− 1) were calculated for conformers l, P, l-6A, l, P, d-6A and d, P, d-6A, which differ only in amino acid chirality.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Autor s matičnim brojem:
Srećko Kirin, (192540)

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