(1,2)--Aminoindanol and (1,2)--aminoindanol, denoted as -AI and -AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in -AI, which is absent in -AI. They also differ by the number of conformers under supersonic jet conditions, one for -AI and two for -AI. One-photon and resonance-enhanced two-photon photoelectron circular dichroism (PECD) spectra are obtained for the two molecules. One-photon ionisation above 11 eV results in molecular fragmentation, with very similar fragmentation pathways for -AI and -AI. Identical PECD spectra for different fragments allow associating them with reactions occurring from the same parent ion within the same electronic state. The shape of the PECD spectra is sensitive to configuration, conformation, and intramolecular hydrogen bonding. Two-photon PECD, being conformer specific, shows that the PECDs of the two ring-puckering conformers of -AI have identical signs but different values.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d4cp04248dDOI Listing

Publication Analysis

Top Keywords

intramolecular hydrogen
12
-ai -ai
12
pecd spectra
12
-ai
9
hydrogen bonding
8
photoelectron circular
8
circular dichroism
8
-ai identical
8
role intramolecular
4
bonding photoelectron
4

Similar Publications

(1,2)--Aminoindanol and (1,2)--aminoindanol, denoted as -AI and -AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in -AI, which is absent in -AI. They also differ by the number of conformers under supersonic jet conditions, one for -AI and two for -AI. One-photon and resonance-enhanced two-photon photoelectron circular dichroism (PECD) spectra are obtained for the two molecules.

View Article and Find Full Text PDF

Noncovalent carbon bonding (C-bonding), a recently explored σ-hole interaction, has primarily been characterized through X-ray structural and computational studies. Evidence of C-bonds in solution is scarce, especially in highly polar solvents like DMSO where solvation effects typically overshadow weak non-covalent interactions. In this work, we present three novel spiroisatin-based -acyl hydrazones (1-3) in which C-bonds play a critical role in stabilizing the conformation in solution.

View Article and Find Full Text PDF

4'-Selective alkylation of nucleosides has been recognized as one of the ideal and straightforward approaches to chemically modified nucleosides, but such a transformation has been scarce and less explored. In this Letter, we combine a visible-light-mediated photoredox catalysis and hydrogen atom transfer (HAT) auxiliary to achieve β-C(sp)-H alkylation of alcohol on tetrahydrofurfuryl alcohol scaffolds and exploit it for 4'-selective alkylation of nucleosides. The reaction involves an intramolecular 1,5-HAT process and stereocontrolled Giese addition of the resultant radicals.

View Article and Find Full Text PDF

Chitosan (CHT) is a known piezoelectric biomacromolecule; however, its usage is limited due to rapid degradation in an aqueous system. Herein, we prepared CHT film via a solvent casting method and cross-linked in an alkaline solution. Sodium hydroxide facilitated deprotonation, leading to increased intramolecular hydrogen bonding and mechanical properties.

View Article and Find Full Text PDF

Ligand engineering boosts catalase-like activity of gold nanoclusters for cascade reactions combined with glucose oxidase in ZIF-8 matrix.

Anal Chim Acta

February 2025

Tianjian Laboratory of Advanced Biomedical Sciences, Institute of Advanced Biomedical Sciences, Henan International Joint Laboratory of Tumor Theranostic Cluster Materials, Henan Key Laboratory of Crystalline Molecular Functional Materials, College of Chemistry, Zhengzhou University, 450001, Zhengzhou, China. Electronic address:

Background: Integrating natural enzymes and nanomaterials exhibiting tailored enzyme-like activities is an effective strategy for the application of cascade reactions. It is essential to develop a highly efficient and robust glucose oxidase-catalase (GOx-CAT) cascade system featuring controllable enzyme activity, a reliable supply of oxygen, and improved stability for glucose depletion in cancer starvation therapy. However, the ambiguous relationship between structure and performance, and the difficulty in controlling enzyme-mimic activity, significantly hinder their broader application.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!