The investigation of excited state proton transfer mechanism in water-bridged 7-azaindole

Zhang, Yongjia; Zhao, Jinfeng; Li, Yongqing

doi:10.1016/j.saa.2015.08.028

Cited by 28 publications

(14 citation statements)

References 71 publications

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“…The information of wave function has been calculated and analyzed for compounds 1 and 3 in different electronic states via DFT and TDDFT methods, respectively. Most of contemporary researchers have extensively adopted these theoretical methods to investigate photophysical and photochemical reaction mechanisms of organic molecules in the past [9][10][11][12][13][14][15][16][17][18][19][20][21][22]. The whole computational processes are based on the Gaussian 09 program [23].…”

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confidence: 99%

Proton-Transfer and Photo-deamination Reactive Mechanisms Studies of Amines Compounds

Yang¹

2017

CiCC

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The reference [J. Org. Chem. 2015, 80, 10817.10828] has reported that the Quinone Methides (QMs) that are of significant medicinal benefits in biological field can be generated via photo-deamination reaction. In this study, the density functional theory (DFT) and time-dependent DFT (TDDFT) methods have been carried out to investigate the reactive mechanisms of free amines compounds 1 and 3. The excited state hydrogen bonding strengthening mechanism has been demonstrated by analyses of frontier molecular orbitals (MOs). Potential energy surfaces (PESs) calculations have been performed for illustrating excited state intramolecular proton transfer (ESIPT) and photo-deamination reactions of forms 1 and 3. The reactive sites of QM1 and QM3 molecules can be accurately predicted via analyses of ESP.

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confidence: 99%

Proton-Transfer and Photo-deamination Reactive Mechanisms Studies of Amines Compounds

Yang¹

2017

CiCC

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“…S3 ). These phenomenons may be explained with proton transfer mechanism 38 39 40 41 . Therefore, the Raman spectrum obtained from the solid PNTP is not from the PNTP itself, but the dimer structure shown in the insert of Fig.…”

Section: Resultsmentioning

confidence: 96%

The discovery of the hydrogen bond from p-Nitrothiophenol by Raman spectroscopy: Guideline for the thioalcohol molecule recognition tool

Ling

Xie

Liu

et al. 2016

Sci Rep

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Inter- and intra- molecular hydrogen bonding plays important role in determining molecular structure, physical and chemical properties, which may be easily ignored for molecules with a non-typical hydrogen bonding structure. We demonstrated in this paper that the hydrogen bonding is responsible for the different Raman spectra in solid and solution states of p-Nitrothiophenol (PNTP). The consistence of the theoretical calculation and experiment reveals that the intermolecular hydrogen bonding yields an octatomic ring structure (8) of PNTP in the solid state, confirmed by the characteristic S-H---O stretching vibration mode at 2550 cm−1; when it comes to the solution state, the breakage of hydrogen bond of S-H---O induced the S-H stretching vibration at 2590 cm−1. Our findings may provide a simple and fast method for identifying the intermolecular hydrogen bonding.

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“…With regard to our work, we have accomplished the theoretical calculationfor all parametersbased on the DFT and TDDFT methods by the Gaussian 09 program suite 42 . The TDDFT method has been extensivelyapplied toinvestigate the hydrogen bond dynamics in the S 1 state 5 6 7 8 9 10 11 12 43 44 45 46 47 48 49 50 51 52 53 54 . Herein, the Becke One Parameter Hybrid Functionals (B1B95) has been used 54 .…”

Section: Discussionmentioning

confidence: 99%

Theoretical Study of the ESIPT Process for a New Natural Product Quercetin

Yang

Zhao

2016

Sci Rep

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The investigation of excited-state intramolecular proton transfer (ESIPT) has been carried out via the density functional theory (DFT) and the time-dependent density functional theory (TDDFT) method for natural product quercetin in dichloromethane (DCM) solvent. For distinguishing different types of intramolecular interaction, the reduced density gradient (RDG) function also has been used. In this study, we have clearly clarified the viewpoint that two kinds of tautomeric forms (K1, K2)originated from ESIPT processconsist inthe first electronic excited state (S1). The phenomenon of hydrogen bonding interaction strengtheninghas been proved by comparing the changes of infrared (IR) vibrational spectra and bond parameters of the hydrogen bonding groups in the ground state with that in the first excited state. The frontier molecular orbitals (MOs)provided visual electron density redistribution have further verified the hydrogen bond strengthening mechanism. It should be noted that the ESIPT process of the K2 form is easier to occur than that of the K1 form via observing the potential energy profiles. Furthermore, the RDG isosurfaces has indicated that hydrogen bonding interaction of the K2 form is stronger than that of the K1 formin the S1 state, which is also the reason why the ESIPT process of the K2 form is easier to occur.

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The investigation of excited state proton transfer mechanism in water-bridged 7-azaindole

Cited by 28 publications

References 71 publications

Proton-Transfer and Photo-deamination Reactive Mechanisms Studies of Amines Compounds

Proton-Transfer and Photo-deamination Reactive Mechanisms Studies of Amines Compounds

The discovery of the hydrogen bond from p-Nitrothiophenol by Raman spectroscopy: Guideline for the thioalcohol molecule recognition tool

Theoretical Study of the ESIPT Process for a New Natural Product Quercetin

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