Cylindrical macrocyclic compounds synthesized by connecting two bowl-shaped calix[3]aramide moieties: structures and chiroptical properties

Sakagami, Ryoko; Saito, Yuuki; Mori, Ryuichi; Satake, Misa; Okayasu, Misaki; Kikkawa, Shoko; Hikawa, Hidemasa; Azumaya, Isao

doi:10.1039/d0ra07060b

Cited by 2 publications

(1 citation statement)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Macrocyclic compounds are important structures and key building blocks in supramolecular chemistry [16][17][18]. Among them, cucurbiturils are a relatively novel family of barrelshaped macrocyclic hosts that can encapsulate guest molecules in their unique large cavities, which are edged by carbonyl oxygen atoms [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

DFT-D4 Insight into the Inclusion of Amphetamine and Methamphetamine in Cucurbit[7]uril: Energetic, Structural and Biosensing Properties

et al. 2021

View full text Add to dashboard Cite

The host–guest interactions of cucurbit[7]uril (CB[7]) as host and amphetamine (AMP), methamphetamine (MET) and their enantiomeric forms (S-form and R-form) as guests were computationally investigated using density functional theory calculations with the recent D4 atomic-charge dependent dispersion corrections. The analysis of energetic, structural and electronic properties with the aid of frontier molecular orbital analysis, charge decomposition analysis (CDA), extended charge decomposition analysis (ECDA) and independent gradient model (IGM) approach allowed to characterize the host–guest interactions in the studied systems. Energetic results indicate the formation of stable non-covalent complexes where R-AMP@CB[7] and S-AMP@CB[7] are more stable thermodynamically than R-MET@CB[7] and S-MET@CB[7] in gas phase while the reverse is true in water solvent. Based on structural analysis, a recognition mechanism is proposed, which suggests that the synergistic effect of van der Waals forces, ion–dipole interactions, intermolecular charge transfer interactions and intermolecular hydrogen bonding is responsible for the stabilization of the complexes. The geometries of the complexes obtained theoretically are in good agreement with the X-ray experimental structures and indicate that the phenyl ring of amphetamine and methamphetamine is deeply buried into the cavity of CB[7] through hydrophobic interactions while the ammonium group remains outside the cavity to establish hydrogen bonds with the portal oxygen atoms of CB[7].

show abstract

Section: Introductionmentioning

confidence: 99%

DFT-D4 Insight into the Inclusion of Amphetamine and Methamphetamine in Cucurbit[7]uril: Energetic, Structural and Biosensing Properties

et al. 2021

View full text Add to dashboard Cite

show abstract

Unveiling the nature of interactions in the supramolecular complex of Cucurbit [7-8] uril with ascorbic acid, dopamine and uric acid for biosensing applications: a computational study

2022

View full text Add to dashboard Cite

Cylindrical macrocyclic compounds synthesized by connecting two bowl-shaped calix[3]aramide moieties: structures and chiroptical properties

Abstract: Chiral macrocyclic compounds whose absolute configurations were derived from the amide bond direction were synthesized by homo coupling of meta-calix[3]aramide derivatives.

Cited by 2 publications

References 48 publications

DFT-D4 Insight into the Inclusion of Amphetamine and Methamphetamine in Cucurbit[7]uril: Energetic, Structural and Biosensing Properties

DFT-D4 Insight into the Inclusion of Amphetamine and Methamphetamine in Cucurbit[7]uril: Energetic, Structural and Biosensing Properties

Unveiling the nature of interactions in the supramolecular complex of Cucurbit [7-8] uril with ascorbic acid, dopamine and uric acid for biosensing applications: a computational study

Contact Info

Product

Resources

About