A DFT/TD-DFT study of thiazolidinedione derivative in dimethylformamide: Cooperative roles of hydrogen bondings, electronic and vibrational spectra

Wang, Dandan; Lü, Rui; Yuan, Minghu; Fu, Aiping; Chu, Tianshu

doi:10.1016/j.saa.2014.01.094

Cited by 15 publications

(6 citation statements)

References 53 publications

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“…Subsequently, both intramolecular and intermolecular photoinduced proton-transfer reactions have been widely investigated. ESIPT plays an important role in chemistry, physics, biochemistry, and other relevant disciplines, since it affects the photophysical and photochemical properties of substances. − An ESIPT-generated dual-fluorescence phenomenon is an ultrafast process occurring on the femto- to picosecond time scale, as reported by Kasha et al in 1979 . Generally, the fluorophore induced by the ESIPT process exhibits a significant Stokes shift compared with the absorption spectrum, because the generated tautomer (T*) has an extremely different structure compared with the normal (N*) structure in the excited state. − …”

Section: Introductionmentioning

confidence: 99%

“…In the present work, we have sought to provide insight into the factors that promote the deamination reactions, and the processes whereby QMs are generated have been dissected. The time-dependent density functional theory (TDDFT) methods have been applied throughout, since they are accurate and time-saving for investigating these photochemical reactions, and have been extensively applied in the past decades. ,− Therefore, we can obtain a reasonable interpretation of the reaction mechanisms leading to QMs.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical Investigation of the Reaction Mechanism of Photodeamination Induced by Excited-State Intramolecular Proton Transfer of Cresol Derivatives

Yang

Zhao

et al. 2018

J. Phys. Chem. A

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The novel photodeamination process of cresol derivatives 1 and 3 has been reported experimentally ( J. Org. Chem . 2015 , 80 , 10817 ). However, a full theoretical interpretation of the mechanism is still lacking. In the present study, we aim to provide insight into the factors that promote the deamination reaction through density functional theory (DFT) and time-dependent DFT methods. Calculated absorption and emission spectra are in good agreement with the experimental results. Hydrogen-bond strengthening in the excited state has been verified by analyzing relevant bond parameters and vibrational frequencies as well as frontier molecular orbitals (FMOs), implying that hydrogen-bond interaction acts as the important parameter for the excited-state intramolecular proton-transfer (ESIPT) reaction. The proton-transfer and deamination reactions have been qualitatively analyzed through Gibbs free-energy reaction profiles in different electronic states. It can be concluded that the ESIPT and photodeamination reactions occur in the excited state. To further illustrate the photodeamination mechanism, the constructed 2D potential-energy surface indicates that the photodeamination reaction is infeasible without the ESIPT reaction. This work provides the first theoretical rationale for ESIPT-induced photodeamination occurring spontaneously because of protonation of a basic nitrogen atom.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation of the Reaction Mechanism of Photodeamination Induced by Excited-State Intramolecular Proton Transfer of Cresol Derivatives

Yang

Zhao

et al. 2018

J. Phys. Chem. A

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“…Therefore, when BBTD is excited from S 0 state to S 1 state, the IR spectrum appears the red-shift of 8 cm −1 . It indicates that hydrogen bonds are slightly enhanced and facilitate excited stated intramolecular proton transfer [68][69][70][71]. In Fig.…”

Section: Ir Spectra and Frontier Molecular Orbitalsmentioning

confidence: 90%

The theoretical study of excited-state intramolecular proton transfer of 2,5-bis(benzoxazol-2-yl)thiophene-3,4-diol

Lan

Yang

et al. 2017

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Computations are all done at DFT-Cam-B3LYP/ lanl2dz level of theory [27][28][29], using Gaussian g09 package [30,31]. Based on similar reports dealing with halogens Cam-B3LYP method is accurate and precise enough to address the problem at hand [32][33][34][35].…”

Section: Methodsmentioning

confidence: 99%

Iodo-Bridged Transition States; New Mechanistic Pathways for Base-Catalyzed Halogen Dance

Sakhaee

Doustkhah

et al. 2020

Chemistry Africa

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First reported by Joseph Bunnet et al., base-catalyzed halogen dance reaction has puzzled chemists for decades, to come up with new ideas regarding the mechanism of this chemical reaction. A series of deprotonation followed by fast metal-halogen exchanges are among the most recent mechanisms reported so far. Using density functional theory, DFT, computations and focused on the Bunnet type isomerization halogen dance reactions of iodobenzene derivatives, iodo-bridged transition state, TS, are proposed. The new TS is then used to lay out 8 possible isomerization and 18 possible disproportionation paths. The possible mechanistic pathways are then carefully analyzed based on TS's energy and protonation/deprotonation steps to find the most suitable pathways. These mechanistic pathways, sketch a comprehensive pattern for base-catalyzed halogen dance. There is still a lot to study in the chemistry of poly halogenated aryls.

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A DFT/TD-DFT study of thiazolidinedione derivative in dimethylformamide: Cooperative roles of hydrogen bondings, electronic and vibrational spectra

Cited by 15 publications

References 53 publications

Theoretical Investigation of the Reaction Mechanism of Photodeamination Induced by Excited-State Intramolecular Proton Transfer of Cresol Derivatives

Theoretical Investigation of the Reaction Mechanism of Photodeamination Induced by Excited-State Intramolecular Proton Transfer of Cresol Derivatives

The theoretical study of excited-state intramolecular proton transfer of 2,5-bis(benzoxazol-2-yl)thiophene-3,4-diol

Iodo-Bridged Transition States; New Mechanistic Pathways for Base-Catalyzed Halogen Dance

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