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Density-functional theory of the catnip molecule, nepetalactone

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Abstract

Nepetalactones belongs to the group of iridoid monoterpenoids, which are present in the aerial parts of nepeta plants. Nepetalactone is an attractant to feline animals causing euphoric effects, while it is a repellent to mosquitoes and cockroaches. It is also a pheromone for several insect aphid species. The main objective of this research was to study the electronic and spectral properties of nepetalactones. We investigated its structural properties using hybrid density-functional theory of B3LYP and WB97XD functional with the 6-311++G(d,p) basis set to optimize the geometry, and then computed the electronic structure, HOMO–LUMO, natural bond orbitals, molecular electronic potential and its contour map. We also obtained spectral signatures of NMR, IR and UV–Vis, and compared them with experimental data from the literature. The DFT study provided different electronic and spectral information that will be of value for further research on making new derivatives of nepetalactones for commercial purposes. Nepetalactones have a promising future in the development of novel mosquito repellents for the control of malaria and arboviral diseases.

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Data availability

Data are available upon request.

Code availability

Not applicable.

Abbreviations

DFT:

Density-functional theory

B3LYP:

Becke 3-parameter Lee–Yang–Parr exchange–correlation functional

HOMO:

Highest occupied molecular orbital

LUMO:

Lowest unoccupied molecular orbital

NLO:

Non-linear optical

NMR:

Nuclear magnetic resonance spectroscopy

SCF:

Self consistent field

GIAO:

Gauge‐including atomic orbital

TMS:

Tetramethyl silane

IR:

Infra-red spectroscopy

UV–Vis:

Ultra-violet visible spectroscopy

NBO:

Natural bond orbitals

FMO:

Frontier molecular orbital

NAC:

Natural atomic charges

MEP:

Molecular electrostatic potential

VEDA:

Visualization Energy Distribution Analysis

PED:

Potential energy distribution

ppm:

Parts per million

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Funding

We thanks the Higher Education Commission of Pakistan [Grant No. 21-436 SRGP/R&D/HEC/2014] for their support.

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  1. Department of Chemistry, Islamia College University Peshawar, Peshawar, 25120, Khyber Pakhtunkhwa, Pakistan

    Syed Lal Badshah & Rabiya Jehan

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  1. Syed Lal Badshah
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Correspondence to Syed Lal Badshah.

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Badshah, S.L., Jehan, R. Density-functional theory of the catnip molecule, nepetalactone. Mol Cell Biochem 477, 1139–1153 (2022). https://doi.org/10.1007/s11010-022-04366-8

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