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Experimental and DFT Studies on the FT‐IR, NMR and UV/Vis Spectra of a Xanthene Derivative: The Case of 9‐benzoyl‐3,4,5,6,7,9‐hexahydro‐1 h ‐xanthene‐1,8(2 h )‐dione
Author(s) -
Sima Abdollahi Mrs.,
NematiKande Ebrahim,
Poursattar Marjani Ahmad
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904165
Subject(s) - chemistry , xanthene , density functional theory , bathochromic shift , atomic electron transition , molecular electronic transition , molecular orbital , acetonitrile , spectral line , homo/lumo , time dependent density functional theory , computational chemistry , analytical chemistry (journal) , photochemistry , molecule , fluorescence , organic chemistry , physics , quantum mechanics , astronomy
9‐benzoyl‐3,4,5,6,7,9‐hexahydro‐1 H ‐xanthene‐1,8(2 H )‐dione was synthesized and studied uing FT‐IR, NMR and UV/Vis spectra both experimentally and using density functional theory (DFT) methods. The absoulte average deviation (AAD) between experimental NMR chemical shifts and DFT results calculated at B3LYP/6‐311+g(d,p) level was 3.9 % and 4.8 % for 1 H and 13 C‐NMR, respectively. Scaled quantum mechanical (SQM) method was implemented to scale the calculated harmonic frequencies, and it was found that, the experimental and SQM frequencies are in acceptable agreement with AAD of ∼7 cm −1 . UV/Vis spectra in water, ethanol, acetonitrile and n‐hexane solvents measured experimentally and calculated using time‐dependent CAM‐B3LYP/6‐311+g(d,p) method. Bathochromic shift of some electronic excitations are also discussed based on the linear solvation energy relationships. Molecular orbital, natural transition orbital and hole‐electron analyses were used to further analyze the nature of the electron transitions. In Uv/Vis spectra, only S0→S19 excitation is a charge transfer transition, where the other excitations are local electron transitions.