Investigation of the electronic spectra of ?-pyrone derivatives by the pariser-parr-pople met hod in the variable? approximation

Perel'son, M. E.; Zvolinskii, V. P.; Kagan, G. I.; Sheinker, Yu. N.

doi:10.1007/bf00739454

Cited by 3 publications

(1 citation statement)

References 12 publications

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“…In the case of warfarin, all of the side-chain methylene and methyl protons are completely exchanged with deuterium when a solution of warfarin is prepared in deuterium oxide at pD = 7.45, indicating that under these conditions warfarin exists at least partially as an open chain tautomeric form with a side chain enolizable ketone moiety with enolic hydrogens on either side [59]. Molecular orbital calculations have been used to predict both UV and pmr spectra [60][61][62][63][64][65]. Calculations assuming the 4-hydroxycoumarin tautomeric structure have generally been more successful at predicting experimentally observed spectra than calculations assuming the 2-hydroxychromone tautomeric form, but the agreement between theoretical and experimental spectra was only suggestive, not conclusive.…”

Section: Determining Tautomeric Equilibriamentioning

confidence: 99%

Warfarin: history, tautomerism and activity

Porter

2010

J Comput Aided Mol Des

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The anticoagulant drug warfarin, normally administered as the racemate, can exist in solution in potentially as many as 40 topologically distinct tautomeric forms. Only 11 of these forms for each enantiomer can be distinguished by selected computational software commonly used to estimate octanol-water partition coefficients and/or ionization constants. The history of studies on warfarin tautomerism is reviewed, along with the implications of tautomerism to its biological properties (activity, protein binding and metabolism) and chemical properties (log P, log D, pK (a)). Experimental approaches to assessing warfarin tautomerism and computational results for different tautomeric forms are presented.

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Section: Determining Tautomeric Equilibriamentioning

confidence: 99%

Warfarin: history, tautomerism and activity

Porter

2010

J Comput Aided Mol Des

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Attenuated total reflectance spectroscopy of coumarin organosilane molecules adsorbed on a fused silica surface

Bratescu

Saito

Takai

2010

Applied Surface Science

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Database of Absorption and Fluorescence Spectra of >300 Common Compounds for use in PhotochemCAD

Taniguchi

Lindsey

2018

Photochem & Photobiology

353

258

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The design of new molecules for photochemical studies typically requires knowledge of spectral features of pertinent chromophores beginning with the absorption spectrum (λ ) and accompanying molar absorption coefficient (ε, m cm ) and often extending to the fluorescence spectrum (λ ) and fluorescence quantum yield (Φ ), where the fluorescence properties may be of direct relevance or useful as proxies to gain insight into the nature of the first excited singlet state. PhotochemCAD databases, developed over a period of 30 years, are described here. The previous databases for 150 compounds have been expanded to encompass 339 compounds for which absorption spectra (including ε values), fluorescence spectra (including Φ values) and references to the primary literature have been included where available (552 spectra altogether). The compounds exhibit spectra in the ultraviolet, visible and/or near-infrared spectral regions. The compound classes and number of members include acridines (21), aromatic hydrocarbons (41), arylmethane dyes (11), azo dyes (18), biomolecules (18), chlorins/bacteriochlorins (16), coumarins (14), cyanine dyes (19), dipyrrins (7), heterocycles (26), miscellaneous dyes (13), oligophenylenes (13), oligopyrroles (6), perylenes (5), phthalocyanines (11), polycyclic aromatic hydrocarbons (16), polyenes/polyynes (10), porphyrins (34), quinones (24) and xanthenes (15). A database of 31 solar spectra also is included.

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Investigation of the electronic spectra of ?-pyrone derivatives by the pariser-parr-pople met hod in the variable? approximation

Cited by 3 publications

References 12 publications

Warfarin: history, tautomerism and activity

Warfarin: history, tautomerism and activity

Attenuated total reflectance spectroscopy of coumarin organosilane molecules adsorbed on a fused silica surface

Database of Absorption and Fluorescence Spectra of >300 Common Compounds for use in PhotochemCAD

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