Structural and vibrational investigation of Cis-Trans isomers of potent insecticide allethrin.
Allethrin
DFT calculations
Descriptors
Molecular structure
Vibrational spectra
Journal
Journal of molecular modeling
ISSN: 0948-5023
Titre abrégé: J Mol Model
Pays: Germany
ID NLM: 9806569
Informations de publication
Date de publication:
22 Aug 2022
22 Aug 2022
Historique:
received:
12
03
2022
accepted:
12
08
2022
entrez:
22
8
2022
pubmed:
23
8
2022
medline:
25
8
2022
Statut:
epublish
Résumé
In this research, the optimised structural and vibrational properties of cis-trans isomers of powerful insecticide allethrin were theoretically studied in gas phase and in aqueous and ethanol solutions by using hybrid B3LYP/6-311 + + g(d,p) level of theory. The results revealed that the permittivity of solvent has influence on the properties of both isomers, thus, higher dipole moments and solvation energies are observed in water, a solvent of higher permittivity (78.355) than ethanol. Complete vibrational assignments of both isomers were done by combining the experimental IR spectrum of allethrin with the scaled quantum mechanical force field (SQMFF) methodology and the determination of corresponding scaled force constants in gas phase and aqueous solution are reported. Different signs of dihedral O2C10C6C4 angles of both isomers (negative in cis and positive in trans) support the differences in the vibrational assignments. Natural bond orbital (NBO) calculations suggest that both isomers are highly stable in gas phase and aqueous solution and that the side chains and five member's rings are involved in the n → σ* interactions. However, atoms in molecules (AIM) studies reveal a higher stability of form cis in both media than the trans one. Merz-Kollman (MK), Mulliken and natural population atomic (NPA) charges for both isomers support the higher hydration of trans isomer in aqueous media and, hence, the higher solvation energy in water (ΔG
Identifiants
pubmed: 35995874
doi: 10.1007/s00894-022-05272-y
pii: 10.1007/s00894-022-05272-y
doi:
Substances chimiques
Allethrins
0
Insecticides
0
Solvents
0
Water
059QF0KO0R
Ethanol
3K9958V90M
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
268Informations de copyright
© 2022. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.
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