Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions
AbstractContinuing with our interest in the guanidinium group and the different interactions than can establish, we have carried out a theoretical study of the complexes formed by this cation and the aromatic amino acids (phenylalanine, histidine, tryptophan and tyrosine) using DFT methods and PCM-water solvation. Both hydrogen bonds and cation-π interactions have been found upon complexation. These interactions have been characterized by means of the analysis of the molecular electron density using the Atoms-in-Molecules approach as well as the orbital interactions using the Natural Bond Orbital methodology. Finally, the effect that the cation-π and hydrogen bond interactions exert on the aromaticity of the corresponding amino acids has been evaluated by calculating the theoretical NICS values, finding that the aromatic character was not heavily modified upon complexation. View Full-Text
- Supplementary File 1:
Supplementary (PDF, 1793 KB)
Share & Cite This Article
Trujillo, C.; Rodriguez-Sanz, A.A.; Rozas, I. Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions. Molecules 2015, 20, 9214-9228.
Trujillo C, Rodriguez-Sanz AA, Rozas I. Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions. Molecules. 2015; 20(5):9214-9228.Chicago/Turabian Style
Trujillo, Cristina; Rodriguez-Sanz, Ana A.; Rozas, Isabel. 2015. "Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions." Molecules 20, no. 5: 9214-9228.