Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2023 Feb 26;28(5):2181.
doi: 10.3390/molecules28052181.

Crystal Structure, Photophysical Study, Hirshfeld Surface Analysis, and Nonlinear Optical Properties of a New Hydroxyphenylamino Meldrum's Acid Derivative

Wulan Zeng  1 , Xia Wang  1 , Tao Zhou  1 , Yunju Zhang  2
Affiliations

Crystal Structure, Photophysical Study, Hirshfeld Surface Analysis, and Nonlinear Optical Properties of a New Hydroxyphenylamino Meldrum's Acid Derivative

Wulan Zeng et al. Molecules. .

Abstract

The structural, photophysical, and vibrational properties of a new hydroxyphenylamino Meldrum's acid derivative, 3-((2-hydroxyphenylamino)methylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione (HMD), were studied. The comparison of experimental and theoretical vibrational spectra can help understand basic vibration patterns and provides a better interpretation of IR spectra. The UV-Vis spectrum of HMD was computed using density functional theory (DFT)/B3LYP/6-311 G(d,p) basis set in the gas state, and the maximum wavelength was in accord with the experimental data. The molecular electrostatic potential (MEP) and Hirshfeld surface analysis confirmed O(1)-H(1A)···O(2) intermolecular hydrogen bonds in the HMD molecule. The natural bond orbital (NBO) analysis provided delocalizing interactions between π→π* orbitals and n→σ*/π* charge transfer transitions. Finally, the thermal gravimetric (TG)/differential scanning calorimeter (DSC) and the non-linear optical (NLO) properties of HMD were also reported.

Keywords: Hirshfeld surface analysis; NBO; NLO properties; photophysical properties.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
(1) ORTEP diagram of HMD. (2) Optimized structure of HMD.
Figure 2
Figure 2
The 1D-chained structure for HMD.
Figure 3
Figure 3
The packing arrangement of HMD.
Figure 4
Figure 4
FT−IR and calculated IR for HMD.
Figure 5
Figure 5
Experimental and calculated UV−Vis spectra for HMD.
Figure 6
Figure 6
The four frontier molecular orbitals for HMD.
Figure 7
Figure 7
The molecular electrostatic potential for HMD.
Figure 8
Figure 8
The dnorm Hirshfeld surface for HMD.
Figure 9
Figure 9
The 2D fingerprint maps for HMD.
Figure 10
Figure 10
TG and DSC curves of HMD.
See this image and copyright information in PMC

References

    1. Arcadi A., Calcaterra A., Fabrizi G., Fochetti A., Goggiamani A., Iazzetti A., Marrone F., Mazzoccanti G., Serraiocco A. One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum’s acids. Org. Biomol. Chem. 2022;20:3160–3173. doi: 10.1039/D2OB00289B. - DOI - PubMed
    1. Johnson T.C., Marsden S.P. Three-component synthesis of pyridylacetic acid derivatives by arylation/decarboxylative substitution of Meldrum’s acids. J. Org. Chem. 2022;87:13891–13894. doi: 10.1021/acs.joc.2c01597. - DOI - PMC - PubMed
    1. Yuan L., He L., Zhang X., Liu J., Zhang D., Udayabhaskararao T., Yang F., Zhao Y., Wang D., Zhao H. Dynamic postpolymerization modification based on knoevenagel adducts of Meldrum’s Acid. Macromolecules. 2022;55:6102–6109. doi: 10.1021/acs.macromol.2c00422. - DOI
    1. Cavalli E.S., Mies T., Rzepa H.S., White A.J.P., Parsons P.J., Barrett A.G.M. Pyrimidine nucleosides syntheses by late-stage base heterocyclization reactions. Org. Lett. 2022;24:8931–8935. doi: 10.1021/acs.orglett.2c03152. - DOI - PMC - PubMed
    1. Komogortsev A.N., Melekhina V.G., Lichitsky B.V. Multicomponent protocol for the synthesis of substituted methyl 3-(3-hydroxy-4-oxo-4H-chromen-2-yl)propanoates from 3-hydroxy-4H-chromen-4-one. Synthetic Commun. 2022;52:1664–1671. doi: 10.1080/00397911.2022.2107431. - DOI