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Pyrazolyc 3-hydroxychromones: Regulation of ESIPT reaction by the “flavonol-like” intramolecular hydrogen bonding to carbonyl group oxygen, which dominates over the “alternative” H-bond to heterocyclic nitrogen

Paper ID Volume ID Publish Year Pages File Format Full-Text
27156 44005 2010 11 PDF Available
Title
Pyrazolyc 3-hydroxychromones: Regulation of ESIPT reaction by the “flavonol-like” intramolecular hydrogen bonding to carbonyl group oxygen, which dominates over the “alternative” H-bond to heterocyclic nitrogen
Abstract

Two isomeric pyrazole derivatives of 3-hydroxychromone (3HC) with and without the possibility of the multiple intramolecular hydrogen bonds formation were compared theoretically and experimentally with the aim to find out whether the excited state intramolecular proton transfer (ESIPT) reaction follows the traditional to the most of 3HCs “flavonol-like” direction towards the CO group oxygen or an “alternative” direction towards the heterocyclic nitrogen atom.Quantum-chemical modeling and comparative study of the experimental spectral parameters of the title compounds indicated the preferential realization of “flavonol-like” ESIPT to oxygen channel.The 3HC systems with the “alternative” intramolecular hydrogen bond to nitrogen were characterized as low fluorescent and practically unable to ESIPT with participation of the nitrogen containing heterocyclic unit.

Keywords
3-Hydroxychromone; Pyrazole; Intramolecular hydrogen bonding; Electronic absorption and fluorescence spectra; ESIPT; Quantum-chemical calculations; ESS-analysis
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Pyrazolyc 3-hydroxychromones: Regulation of ESIPT reaction by the “flavonol-like” intramolecular hydrogen bonding to carbonyl group oxygen, which dominates over the “alternative” H-bond to heterocyclic nitrogen
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 209, Issues 2–3, 25 January 2010, Pages 163–173
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us