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

• Published in: Crystals (Basel) 2021-02, Vol.11 (2), p.146
• Main Authors: Przybył, Anna, Grzeskiewicz, Anita, Kubicki, Maciej
• Format: Article
• Language: English
• Subjects: Alanine; alkaloid derivatives; Amino acids; atoms-in-molecules topological analysis; Bonding strength; Chemistry; Critical point; Crystal structure; Electron density; Glycine; Hydrogen bonds; interaction energies; Leucine; Nicotine; NMR; Nuclear magnetic resonance; Parameter estimation; Solvents; Synthesis; Valine; weak hydrogen bonds; weak interactions
• ISSN: 2073-4352; 2073-4352
• DOI: 10.3390/cryst11020146

Eight new (–)-(N-[(AA)-(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.