Raman Optical Activity of N-Acetyl-L-Cysteine in Water and in Methanol: The "Clusters-in-a-Liquid" Model and ab Initio Molecular Dynamics Simulations.
Raman optical activity
ab initio molecular dynamics
conformational flexibility
conformational search
solute-solvent interactions
Journal
Chemphyschem : a European journal of chemical physics and physical chemistry
ISSN: 1439-7641
Titre abrégé: Chemphyschem
Pays: Germany
ID NLM: 100954211
Informations de publication
Date de publication:
03 06 2022
03 06 2022
Historique:
revised:
29
03
2022
received:
09
03
2022
pubmed:
31
3
2022
medline:
7
6
2022
entrez:
30
3
2022
Statut:
ppublish
Résumé
Raman and Raman Optical Activity (ROA) spectra of N-acetyl-L-cysteine (NALC), a flexible chiral molecule, were measured in water and in methanol to evaluate the solvent effects. Two different solvation approaches, that is, the DFT based "clusters-in-a-liquid" solvent model and the ab initio molecular dynamics (AIMD) simulations, were applied to simulate the Raman and ROA spectra. Systematic conformational searches were carried out using a recently developed conformational searching tool, CREST, with the inclusion of polarizable continuum model of water and of methanol. The CREST candidates of NALC and the NALC-solvent complexes were re-optimized and their Raman and ROA simulations were done at the B3LYP-D3BJ/def2-TZVP and the B3LYP-aug-cc-pVDZ//cc-pVTZ levels. Also, AIMD simulations, which includes some anharmonic effects and all intermolecular interactions in solution, were performed. By empirically weighting the computed Raman and ROA spectra of each conformer, good agreements with the experimental data were achieved with both approaches, while AIMD offered some improvements in the carbonyl and in the low wavenumber regions over the static DFT approach. The pros and cons of these two different approaches for accounting the solvent effects on Raman and ROA of this flexible chiral system will also be discussed.
Identifiants
pubmed: 35353934
doi: 10.1002/cphc.202200161
doi:
Substances chimiques
Solvents
0
Water
059QF0KO0R
Acetylcysteine
WYQ7N0BPYC
Methanol
Y4S76JWI15
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200161Subventions
Organisme : Natural Sciences and Engineering Research Council of Canada
Organisme : Canada Foundation for Innovation
Organisme : Alberta Enterprise of Advanced Education
Organisme : University of Alberta
Organisme : DFG
ID : Br 5494/1-1.
Organisme : DFG
ID : Br 5494/1-1
Organisme : Tier I Canada Research Chair in Chirality and Chirality Recognition
Informations de copyright
© 2022 Wiley-VCH GmbH.
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