Spectroscopic and quantum-chemical study of molecular interactions of iso-quinolinium ylids in polar solutions

Babusca, Daniela; Morosanu, Ana Cezarina; Dimitriu, Dan Gheorghe; Dorohoi, Dana Ortansa; Cheptea, Corina

doi:10.1080/15421406.2020.1731099

Cited by 4 publications

(8 citation statements)

References 24 publications

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“…All cycloimmonium ylids are characterized by a high-wavelength electronic absorption band (usually placed in the visible range) that is attributed to an internal charge transfer (ICT) from the carbanion toward the heterocycle and is very sensitive to the solvent nature [3][4][5][6][7][8]. This band shifts to high wavenumbers when the ylid is passed from nonpolar or non-protic solvents to polar and protic ones; it disappears or its intensity diminishes in acid media [3,7].…”

Section: Introductionmentioning

confidence: 99%

“…As dipolar and polarizable molecules, cycloimmonium ylids are used, in small concentrations, as sounders in liquids in order to obtain information about the nature and the strength of the molecular interactions in solutions [5][6][7][8]21].…”

Section: Introductionmentioning

confidence: 99%

“…In order to illustrate the importance of solvents' empirical scales in characterizing the nature and strength of molecular interactions and in estimating the excited-state dipole moment of the solute molecules, we have chosen four cycloimmonium ylids: two with common heterocycle and two pairs with common carbanions. These molecules were previously studied separately from a spectral point of view in binary and ternary solutions [5][6][7][8][22][23][24]. The chosen cycloimmonium molecules show electronic absorption bands in the UV range of the π − π * type and a visible band of the n−π * type [3].…”

Section: Introductionmentioning

confidence: 99%

“…The UV bands are of high intensity and low sensitivity to the solvent nature, but the visible absorption band is of low intensity, disappears in acid media and shifts to blue when the solute molecules pass through a non-polar/aprotic solvent to a polar/protic solvent. Based on these characteristics, the electronic visible band was attributed to an intramolecular charge transfer (ICT) transition from the ylid carbanion toward its heterocycle [3,[6][7][8].…”

Section: Introductionmentioning

confidence: 99%

“…In this situation, the researchers combined [5,8,37] the theoretical and empirical correlations using multi-parametric linear relations between the spectral characteristics of the solute and the solvent parameters in order to assure good correspondence between the experimental and computed results. Usually, equations of the type (5) are used to describe the solvent influence on the electronic bands of the solutes.…”

mentioning

confidence: 99%

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Solvatochromic and Computational Study of Some Cycloimmonium Ylids

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This article contains a comparative spectral analysis corroborated with the quantum mechanical computations of four cycloimmonium ylids. The spectral shift of the visible electronic absorption band of the studied molecules in 20 solvents with different empirical parameters is expressed by linear multi-parametric dependences that emphasize the intramolecular charge transfer (ICT) process. The nature of molecular interactions and their contribution to the spectral shift of the visible ICT band of solutes are also established in this manuscript. The results of the statistical analysis are used to estimate the cycloimmonium ylids’ excited dipole moment by the variational method, using the hypothesis of McRae. The importance of the structure of both the heterocycle and carbanion substituents to the stability and reactivity of the studied cycloimmonium ylids is underlined by the quantum mechanical computations of the molecular descriptors.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Solvatochromic and Computational Study of Some Cycloimmonium Ylids

Babusca,

Vleoanga,

Dorohoi

2024

Liquids

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A bis indole analog molecule fluorescent probe for living cell staining

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Intermolecular Interactions in Binary and Ternary Solutions of a Zwitterionic Compound Studied by Solvatochromism

2023

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The 1-dithiocarboxy-2-ethoxy-1-(isoquinolin-2-yl)-2-oxoethan-1-ylid (iQTCY) zwitterionic molecule has been studied by computational and spectral means in order to establish some of its structural parameters in the ground electronic state as well as the nature and the strength of its universal and specific interactions with different solvents. The prevalence of the orientation–induction interactions in the diluted solutions of iQTCY in aprotic solvents and the additional specific interactions by hydrogen bonds (HB) in the protic solvents were demonstrated. Three theoretical models were comparatively used to estimate the composition of the first solvation shell of the iQTCY molecule in ternary solutions. The difference between the interaction energies in molecular pairs solute–solvent was computed based on the statistical cell model of ternary solutions of iQTCY in mixtures of water–ethanol and water–methanol. Using the electro-optical parameters computed by the quantum-mechanical technique and the results of the solvatochromic study, the excited state dipole moment of iQTCY was estimated within the limit of the variational method applicable to molecules that show only an absorption electronic spectrum.

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Spectroscopic and quantum-chemical study of molecular interactions of iso-quinolinium ylids in polar solutions

Cited by 4 publications

References 24 publications

Solvatochromic and Computational Study of Some Cycloimmonium Ylids

Solvatochromic and Computational Study of Some Cycloimmonium Ylids

A bis indole analog molecule fluorescent probe for living cell staining

Intermolecular Interactions in Binary and Ternary Solutions of a Zwitterionic Compound Studied by Solvatochromism

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