Intramolecular hydrogen bonds interactions in the isomers of the bilirubin molecule: DFT and QTAIM analysis.
Bilirubin
Conformers
DFT
Hydrogen bonds
Journal
Journal of molecular modeling
ISSN: 0948-5023
Titre abrégé: J Mol Model
Pays: Germany
ID NLM: 9806569
Informations de publication
Date de publication:
18 Sep 2023
18 Sep 2023
Historique:
received:
25
07
2023
accepted:
02
09
2023
medline:
19
9
2023
pubmed:
18
9
2023
entrez:
17
9
2023
Statut:
epublish
Résumé
Bilirubin is an important molecule, used as a marker of some liver diseases, and it can also be toxic and cause jaundice, especially in newborns. The main treatment for neonatal jaundice is phototherapy with blue light, which is still widely studied because the photophysical processes involved are not fully understood. Calculations based on the density functional theory (DFT) at M062X/6-31G(d,p) level were performed in order to evaluate the structural, electronic, and topological properties of bilirubin isomers. It was found that the ZZ conformation can form a greater number of hydrogen bonds, which gives the isomer greater energy stabilization compared to the other ZE, EZ, and EE isomers, and that the EE isomer is the conformer with the lowest energy of stabilization. The hydrogen bonds were characterized by the quantum theory of atoms in molecules (QTAIM) and for the ZZ isomer four hydrogen bonds (HBs) were found classified as intermediate, ∇
Identifiants
pubmed: 37718354
doi: 10.1007/s00894-023-05720-3
pii: 10.1007/s00894-023-05720-3
doi:
Substances chimiques
Bilirubin
RFM9X3LJ49
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
318Subventions
Organisme : Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
ID : 001
Organisme : Fundação de Amparo à Pesquisa do Estado de São Paulo
ID : 2013/08293-7 and Grant 2017/11485-6
Informations de copyright
© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.
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