Computational and Experimental Studies of (2,2)-Bis(indol-1-yl-methyl)acetate Suggest the Importance of the Hydrophobic Effect in Aromatic Stacking Interactions was written by Pang, Yuan-Ping;Miller, Jennifer L.;Kollman, Peter A.. And the article was included in Journal of the American Chemical Society in 1999.Computed Properties of C11H11NO2 This article mentions the following:
To understand the driving forces of aromatic stacking interactions in water, we have performed conformational searches, mol. dynamics simulations, potential of mean force (PMF) and free energy perturbation (FEP) calculations, syntheses, and NMR studies on sodium (2,2)-bis(indol-1-yl-methyl)acetate (1), sodium 3-indol-1-yl-2-methyl-propionate (2), and sodium 3-indol-1-yl-propionate (3). The conformational searches on 1 revealed that the isobutyric acid linker of 1 allows the mol. to adopt the tilted T-shaped stacked, off-center stacked, face-to-face stacked, and non-stacked conformations in a vacuum. The PMF and FEP calculations suggested that the most thermodynamically stable conformers in water are the tilted T-shaped stacked and non-stacked conformers. Independent NMR spectroscopic studies of 1-3 revealed that both the tilted T-shaped stacked and non-stacked conformers are populated in D2O and in d6-DMSO, and they are in a rapid equilibrium Furthermore, the NMR studies found (i) a larger population of the tilted T-shaped stacked conformation of 1 at 22 ° in D2O than in d6-DMSO and (ii) more different populated stacked conformations of 1 at 60° in D2O than in d6-DMSO. One would expect larger populations of the stacked conformations in d6-DMSO, whose dielec. constant is smaller than that of water, if the electrostatic interaction were the only driving force of the aromatic stacking interactions. The results, therefore, suggest that the hydrophobic effect plays an important role in the stacking interaction of 1 in water. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Computed Properties of C11H11NO2).
3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Computed Properties of C11H11NO2
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles