NMR multinuclear study (13C, 14N, 17O) of indane‐1,3‐diones

Петрова, М. В.; Liepiņš, Edvards; Pauliņš, J.; Gudriniece, E.

doi:10.1002/mrc.1260300305

Cited by 15 publications

(9 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The values of the protontransfer barriers for compound 4, 2.22 in CHCl 3 and 2.40 kcal mol -1 in DMSO, indicate an extremely fast proton-transfer process.The values of the proton-transfer barriers of tautomerization a f c are quite large (in the range of 54.57-72.95 kcal mol -1 ), and tautomerization should not occur. The absence of the signal at about 55-60 ppm for C9(H) carbon atoms for 1-4 and DEPT-135 experiments in CDCl 3 and DMSO-d 6 confirm the exclusion of tautomer c 8,15,33. …”

supporting

confidence: 59%

Theoretical and Spectroscopic Study of 2-Substituted Indan-1,3-diones: A Coherent Picture of the Tautomeric Equilibrium

et al. 2007

View full text Add to dashboard Cite

The structures of some 2-substituted indan-1,3-diones are investigated in the gas phase and solution using quantum chemical calculations and spectral (NMR, IR, and UV) measurements. The influence of the substituent at the 2-position on the tautomeric equilibrium of 2-substituted indan-1,3-diones in solvents with different polarity is evaluated. It is shown that the equilibrium in 2-formyl-indan-1,3-dione and 2-acetyl-indan-1,3-dione is shifted to the 2-hydroxyalkylidene-indan-1,3-dione tautomer, while 2-carboxyamide-indan-1,3-dione exists as a mixture of two tautomers, 2-(hydroxyaminomethylidene)-indan-1,3-dione and 2-carboamide-1-hydroxy-3-oxo-indan, with extremely fast proton transfer between them. The situation for 2-carboxy-indan-1,3-dione is quite different - on the basis of the analysis of the obtained results, the possible existence of an anionic form of 2-carboxy-indan-1,3-dione in solution can be inferred.

show abstract

supporting

confidence: 59%

Theoretical and Spectroscopic Study of 2-Substituted Indan-1,3-diones: A Coherent Picture of the Tautomeric Equilibrium

et al. 2007

View full text Add to dashboard Cite

show abstract

“…A further comparison can be made for compound 1 with some indane-1,3-diones. 11 While a comparable geometry is assured for both systems by sp 2 hybridisation of all the carbons of the five-membered ring, a rough deshielding of ∆δ = 25 is observed for O 1 , O 3 compared with the shifts for the corresponding oxygens of the indane-1,3-diones. 11 This finding is in good agreement with the known influence of the dihedral angle in α-diketones 7a,8 and indicates that substitution of a carbonyl group by a vinylic group will modify the 17 O NMR chemical shifts, which are dependent on the dihedral angles.…”

Section: Resultsmentioning

confidence: 95%

“…11 While a comparable geometry is assured for both systems by sp 2 hybridisation of all the carbons of the five-membered ring, a rough deshielding of ∆δ = 25 is observed for O 1 , O 3 compared with the shifts for the corresponding oxygens of the indane-1,3-diones. 11 This finding is in good agreement with the known influence of the dihedral angle in α-diketones 7a,8 and indicates that substitution of a carbonyl group by a vinylic group will modify the 17 O NMR chemical shifts, which are dependent on the dihedral angles. To our knowledge, an 17 O NMR study of this important feature for carbonyl groups conjugated with vinylic groups has not been reported, so our observations could be regarded as a preliminary study related to this phenomenon.…”

Section: Resultsmentioning

confidence: 95%

Conformations of vicinal-triketones. A theoretical and 17O NMR approach

Cerioni

Plumitallo

Mocci

et al. 2001

J. Chem. Soc., Perkin Trans. 2

View full text Add to dashboard Cite

The conformations of a representative group of vicinal triketones have been studied by 17 O NMR spectroscopy and, for some of them, DFT calculations have been performed in order to rationalize the results and gain an insight into their geometry; 17 O NMR chemical shifts have also been computed by the GIAO method. A dependence of chemical shifts on intercarbonyl dihedral angles, like that observed for α-dicarbonyl systems, has been observed. A constraint to changing conformation, which overrides steric destabilization, has also been observed.

show abstract

“…An example of the use of this chemical process is the modification of the 2-acetylindan-1, 3-dione abbreviated as 2AID or its derivatives. These substances are physiologically active agents showing strong UV absorption in a range between 280 and 330 nm with interesting photophysical properties [65]. The main structural characteristic of 2AID is the presence of a strong intramolecular hydrogen bond (IMHB) ensuring an increased photostability [66].…”

Section: Organometallic Complexesmentioning

confidence: 99%

Artificial Sun Protection: Sunscreens and Their Carrier Systems

Villalobos-Hernández¹,

Müller‐Goymann²

2006

CDD

View full text Add to dashboard Cite

The formulation of sunscreens products requires information about the properties of the substances responsible for the sun protection, their action mechanisms and the vehicles used for their administration. The improvement of the performance of sunscreen substances by a modification of their chemical, physical and technological properties or by the use of conventional and novel carriers is described in this review. The sun protection achieved by the use of sunscreens incorporated into carriers in terms of the sun protection factor (SPF) and other performance indices is also shown. Current manufacturing methods to incorporate sunscreen substances into vehicles are briefly described. Furthermore, basic information related to the dermatological effects of the UV radiation classified according to the different spectral regions of the UV radiation is presented in this manuscript.

show abstract

NMR multinuclear study (¹³C, ¹⁴N, ¹⁷O) of indane‐1,3‐diones

Cited by 15 publications

References 6 publications

Theoretical and Spectroscopic Study of 2-Substituted Indan-1,3-diones: A Coherent Picture of the Tautomeric Equilibrium

Theoretical and Spectroscopic Study of 2-Substituted Indan-1,3-diones: A Coherent Picture of the Tautomeric Equilibrium

Conformations of vicinal-triketones. A theoretical and 17O NMR approach

Artificial Sun Protection: Sunscreens and Their Carrier Systems

Contact Info

Product

Resources

About