UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONS

Experimental and computational analysis of spectroscopic parameters of L-ascorbic acid (vitamin C) and its tautomers was investigated by Density Functional Theory (DFT) using B3LYP method. The optimized geometries and calculated vibrational frequencies were evaluated. The latter was compare with tho...

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Autores principales:	DABBAGH,HUSSEIN A, AZAMI,FATEMEH, FARROKHPOUR,HUSSEIN, CHERMAHINI,ALIREZA NAJAFI
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2014
Materias:	Vitamin C tautomers UV-VIS NMR FT-IR
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000300013
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spelling	oai:scielo:S0717-970720140003000132014-12-15UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONSDABBAGH,HUSSEIN AAZAMI,FATEMEHFARROKHPOUR,HUSSEINCHERMAHINI,ALIREZA NAJAFI Vitamin C tautomers UV-VIS NMR FT-IR Experimental and computational analysis of spectroscopic parameters of L-ascorbic acid (vitamin C) and its tautomers was investigated by Density Functional Theory (DFT) using B3LYP method. The optimized geometries and calculated vibrational frequencies were evaluated. The latter was compare with those of experimental values. The λmax values of L-ascorbic acid were found 259 (at pH = 3) experimentally, 238 and 247 nm calculated in the gas and water phase at TD-DFT methods, respectively. The experimental order of υ(Ο-Η) modes was obtained at υ(O3-Η3) > (O6-Ho6) > (O2-H2) > (O5-Ho5). The theoretical orders were calculated at υ(O6-Ho6) > (O2-H2) > (O5-Ho5) > (O3-H3) and υ(O3-H3) > (O5-Ho5) > (O6-Ho6) > (O2-H2), respectively, in the gas phase and aqueous phase. The highest wave number of tautomers (S,Z)-3,5,6-trihydroxy-2-oxohex-3-enoic acid (2), (2Z,4E)-2,3,5,6-tetrahydroxyhexa-2,4-dienoic acid (3), (R)-2-((S)-1,2-dihydroxyethyl)-4,5-dihydroxyfuran-3(2H)-one (4) was calculated for the stretching modes O6-Ho6, O3-H3, O6-Ho6 bonds, respectively, in the gas phase. The experimental and theoretical calculations of proton NMR predicted H3 as the most deshilded proton.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.59 n.3 20142014-09-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000300013en10.4067/S0717-97072014000300013
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Vitamin C tautomers UV-VIS NMR FT-IR
spellingShingle	Vitamin C tautomers UV-VIS NMR FT-IR DABBAGH,HUSSEIN A AZAMI,FATEMEH FARROKHPOUR,HUSSEIN CHERMAHINI,ALIREZA NAJAFI UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONS
description	Experimental and computational analysis of spectroscopic parameters of L-ascorbic acid (vitamin C) and its tautomers was investigated by Density Functional Theory (DFT) using B3LYP method. The optimized geometries and calculated vibrational frequencies were evaluated. The latter was compare with those of experimental values. The λmax values of L-ascorbic acid were found 259 (at pH = 3) experimentally, 238 and 247 nm calculated in the gas and water phase at TD-DFT methods, respectively. The experimental order of υ(Ο-Η) modes was obtained at υ(O3-Η3) > (O6-Ho6) > (O2-H2) > (O5-Ho5). The theoretical orders were calculated at υ(O6-Ho6) > (O2-H2) > (O5-Ho5) > (O3-H3) and υ(O3-H3) > (O5-Ho5) > (O6-Ho6) > (O2-H2), respectively, in the gas phase and aqueous phase. The highest wave number of tautomers (S,Z)-3,5,6-trihydroxy-2-oxohex-3-enoic acid (2), (2Z,4E)-2,3,5,6-tetrahydroxyhexa-2,4-dienoic acid (3), (R)-2-((S)-1,2-dihydroxyethyl)-4,5-dihydroxyfuran-3(2H)-one (4) was calculated for the stretching modes O6-Ho6, O3-H3, O6-Ho6 bonds, respectively, in the gas phase. The experimental and theoretical calculations of proton NMR predicted H3 as the most deshilded proton.
author	DABBAGH,HUSSEIN A AZAMI,FATEMEH FARROKHPOUR,HUSSEIN CHERMAHINI,ALIREZA NAJAFI
author_facet	DABBAGH,HUSSEIN A AZAMI,FATEMEH FARROKHPOUR,HUSSEIN CHERMAHINI,ALIREZA NAJAFI
author_sort	DABBAGH,HUSSEIN A
title	UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONS
title_short	UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONS
title_full	UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONS
title_fullStr	UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONS
title_full_unstemmed	UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONS
title_sort	uv-vis, nmr and ft-ir spectra of tautomers of vitamin c. experimental and dft calculations
publisher	Sociedad Chilena de Química
publishDate	2014
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000300013
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UV-VIS, NMR AND FT-IR SPECTRA OF TAUTOMERS OF VITAMIN C. EXPERIMENTAL AND DFT CALCULATIONS

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