Weak Interactions in the Structures of Newly Synthesized (–)-Cytisine Amino Acid Derivatives

Crystals

AnnaK. Przybył¹  AnitaM. Grzeskiewicz¹  Maciej Kubicki¹ 

[1] Faculty of Chemistry, A. Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland;

关键词: alkaloid derivatives;    weak interactions;    weak hydrogen bonds;    interaction energies;    atoms-in-molecules topological analysis;   

DOI  :  10.3390/cryst11020146

来源: DOAJ

【 摘 要 】

Eight new (–)-(N-[(AmAc)-(N-phtaloyl)]cytisines (where AA is amino acid: glycine, β-alanine, D,L-valine, L-valine, L-isoleucine, L-leucine, D-leucine and D,L-phenyloalanine), were synthesized and fully spectroscopically characterized (NMR, FTIR and MS). For two of these compounds, N-[glycine-(N-phtaloyl)]cytisine and N-[L-isoleucine-(N-phtaloyl)]cytisine, X-ray crystal structures were obtained and used as the basis for an in-depth analysis of intermolecular interactions and packing energies. The structural geometrical data (weak hydrogen bonds, π···π interactions, etc.) were compared with the energies of interactions and the topological characteristics (electron density, Laplacian at the appropriate critical point) based on the atoms-in-molecules theory. The results suggest that there is no straightforward connection between the geometry of point-to-point interactions and the molecule-to-molecule energies. Additionally, the usefulness of the transfer of multipolar parameters in estimating of critical points’ characteristics have been confirmed.

【 授权许可】

Unknown