Naslov
1, 9-Substituted anthracene amino-acid conjugates: a study by NMR-crystallography

Autori
Perić, Berislav ; Szalontai, Gabor ; Kirin, Srećko I.

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Smarter 6 : Meeting on Structure Elucidation by Combining Magnetic Resonance, Computation, Modeling and Diffraction : Book of Abstracts / - Ljubljana : National Institute of Chemistry Ljubljana, 2018, 62-62

ISBN
978-961-6104-39-5

Skup
6th SMARTER conference, Structure elucidation by combining Magnetic Resonance, Computational Modelling and Diffraction

Mjesto i datum
Ljubljana, Slovenija, 02.09.2018. - 06.09.2018

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
anthracene ; amino acids ; NMR ; crstallography

Sažetak
Amino acid substituted anthracene conjugates possess several modes of aggregation in solid state such as stacking interactions between anthracene cores and hydrogen bonds between amide groups. By using one amino acid enantiomer, modes for solid-state aggregation are reduced and consistent only with non-centrosymmetric space groups. During our synthesis of 1, 9-substituted anthracenes, phenylalanine (1) glycine-phenylalanine (2) and valine (3), we were able to grow crystals suitable for X-ray diffraction from 1 and 2, but failed in case of 3. The crystalline phases of all three compounds were checked by powder X-ray diffraction and analysed by solid-state (ss)NMR measurements (13C CP and CPNQS MAS). Solid state structures for 1 and 2 were determined by single-crystal X-ray diffraction and GIPAW (Gauge Including Projector Augmented Waves)[2] calculations for C chemical shieldings were performed to obtain benchmark correlation between experimental and predicted NMR shifts for characteristic carbon atoms in this class of compounds. The structural model for 3 was obtained through combination of powder X-ray diffraction analysis, pseudopotential-DFT optimizations and ssNMR measurements. The latter provide molecular level and crystal structure information which can serve as constraints in the structure selection process. The GIPAW predicted chemical shifts were in good agreement with the experimental values and consistent with the non-equivalent orientation of the isopropyl groups with respect to the central anthracene core. The pseudopotential-DFT optimizations and GIPAW calculations were performed by program Quantum Espresso.[3] REFERENCES: [1] R. K. Harris, Encyclopedia of Magnetic Resonance, 2008, John Wiley & Sons, Ltd. [2] C. J. Pickard, F. Mauri, Phys. Rev. B, 2001, 63, 245101. [3] P. Giannozzi et al., J. Phys.: Condens. Matter, 2009, 21, 395502.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA