The structure of two 2-acyl-1,3-indandiones

Korp, James D.; Bernal, Ivan; Lemke, Thomas

doi:10.1107/s0567740880003408

Cited by 29 publications

(10 citation statements)

References 5 publications

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“…In the electronic ground state (S 0 ), the most stable conformer is the tautomer A (S 0 A ; reactant state) with exocyclic double bond (Scheme 1), in agreement with experimental results and calculations 39–43 . Therefore, other rotamers are not considered as reactants, as they have not been spectroscopically observed in solution at room temperature.…”

Section: Discussionsupporting

confidence: 81%

“…2-acetylindan-1,3-dione (AID) is a ß-diketone with an exocyclic double bond and has been shown to exist as exocyclic enol form (see molecular structure in Figure 1) in solution by various theoretical and experimental studies 39–43 . Apart from being a bio-active drug molecule with antibacterial and anticoagulant activities, it is a promising chelating and sunscreen agent 44–46 .…”

Section: Introductionmentioning

confidence: 99%

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Excited-state intramolecular proton transfer of 2-acetylindan-1,3-dione studied by ultrafast absorption and fluorescence spectroscopy

Verma

Steinbacher

Schmiedel

et al. 2015

Structural Dynamics

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We employ transient absorption from the deep-UV to the visible region and fluorescence upconversion to investigate the photoinduced excited-state intramolecular proton-transfer dynamics in a biologically relevant drug molecule, 2-acetylindan-1,3-dione. The molecule is a ß-diketone which in the electronic ground state exists as exocyclic enol with an intramolecular H-bond. Upon electronic excitation at 300 nm, the first excited state of the exocyclic enol is initially populated, followed by ultrafast proton transfer (≈160 fs) to form the vibrationally hot endocyclic enol. Subsequently, solvent-induced vibrational relaxation takes place (≈10 ps) followed by decay (≈390 ps) to the corresponding ground state.

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Section: Discussionsupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Excited-state intramolecular proton transfer of 2-acetylindan-1,3-dione studied by ultrafast absorption and fluorescence spectroscopy

Verma

Steinbacher

Schmiedel

et al. 2015

Structural Dynamics

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“…Such a molecular geometry of the b-diketone fragment in 2, 3 and 4 is in agreement with what is found in similar 1,3-indandione and indan-1-one derivatives like the 2-pivaloyl-1,3-indandione structure [35], 2-acetyl-1,3-indandione [36], 2-(hydroxy(amino)methylidene)-1,3-indandione [9] and 2-acylindan-1-one [37].…”

Section: Crystal Structure Descriptions Of Compounds 2 3 Andsupporting

confidence: 86%

Experimental and theoretical study on the structure and optical properties of 2-acyl-1,3-indandiones – Conformational effects

Ahmedova¹,

Pavlović²,

Zhiryakova³

et al. 2010

Journal of Molecular Structure

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“…2‐Acetylindan‐1,3‐dione (2AID) and its derivatives are known as physiologically active agents [2]. The structure and the possibility for tautomerism of 2AID have also been intensively studied [3–7]. Recently, it was shown that 2AID has interesting photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

2‐Acetylindan‐1,3‐dione and its Cu²⁺ and Zn²⁺ complexes as promising sunscreen agents

Ahmedova

Mantareva

Enchev

et al. 2002

Intern J of Cosmetic Sci

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In continuation of a previous spectroscopic and quantum chemical study on 2-acetylindan-1,3-dione (2AID), the spectral properties and photostability of 2AID and its Cu(2+) and Zn(2+) complexes in different solvents are reported. Comparison is made with the photostability of two commercially available sunscreens: benzophenone-3 and octylmethoxycinnamate. 2AID exhibits a higher photostability, high molar absorption coefficient (42 000 m(-1) cm(-1)) at lambda(max) and broad-spectrum UV-protection properties. The hypothesis that the strong intramolecular H-bonding is responsible for the higher photostability was confirmed by studying the photodegradation upon irradiation with UV light of 2AID in hydrogen bond-breaking solvent, DMSO. The data obtained show that 2AID undergoes rapid degradation in this solvent. It is found that Cu(2+) and Zn(2+)-2AID complexes show higher photostability in DMSO than 2AID itself.

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The structure of two 2-acyl-1,3-indandiones

Cited by 29 publications

References 5 publications

Excited-state intramolecular proton transfer of 2-acetylindan-1,3-dione studied by ultrafast absorption and fluorescence spectroscopy

Excited-state intramolecular proton transfer of 2-acetylindan-1,3-dione studied by ultrafast absorption and fluorescence spectroscopy

Experimental and theoretical study on the structure and optical properties of 2-acyl-1,3-indandiones – Conformational effects

2‐Acetylindan‐1,3‐dione and its Cu²⁺ and Zn²⁺ complexes as promising sunscreen agents

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The structure of two 2-acyl-1,3-indandiones

Cited by 29 publications

References 5 publications

Excited-state intramolecular proton transfer of 2-acetylindan-1,3-dione studied by ultrafast absorption and fluorescence spectroscopy

Excited-state intramolecular proton transfer of 2-acetylindan-1,3-dione studied by ultrafast absorption and fluorescence spectroscopy

Experimental and theoretical study on the structure and optical properties of 2-acyl-1,3-indandiones – Conformational effects

2‐Acetylindan‐1,3‐dione and its Cu2+ and Zn2+ complexes as promising sunscreen agents

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Product

Resources

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2‐Acetylindan‐1,3‐dione and its Cu²⁺ and Zn²⁺ complexes as promising sunscreen agents