4-Carboxyl-2,6-dinitrophenylazohydroxynaphthalenes tautomerism NMR re-explained and other methods verified

Silvia Hristova, Silvia Angelova, Poul Erik Hansen, Liudmil Antonov

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

In two consecutive studies the tautomerism in 4-((2-hydroxynaphthalen-1-yl)diazenyl)-3,5-dinitrobenzoic acid and the structurally similar 1-((2-nitrophenyl)diazenyl)naphthalen-2-ol has been considered from viewpoint of theoretical chemistry, UV–Vis spectroscopy and NMR. Although the theoretical data (at M062X level) show that both compounds exist only as a keto tautomer, the experiment proves existence of the enol form. The difference in the results obtained by UV–Vis spectroscopy and NMR requires a deeper consideration and verification of the NMR approach, which is based on using model compounds to provide the NMR signal pattern of individual tautomers.
OriginalsprogEngelsk
TidsskriftDyes and Pigments
Vol/bind142
Sider (fra-til)226-229
Antal sider4
ISSN0143-7208
DOI
StatusUdgivet - 2017

Citer dette

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title = "4-Carboxyl-2,6-dinitrophenylazohydroxynaphthalenes tautomerism NMR re-explained and other methods verified",
abstract = "In two consecutive studies the tautomerism in 4-((2-hydroxynaphthalen-1-yl)diazenyl)-3,5-dinitrobenzoic acid and the structurally similar 1-((2-nitrophenyl)diazenyl)naphthalen-2-ol has been considered from viewpoint of theoretical chemistry, UV–Vis spectroscopy and NMR. Although the theoretical data (at M062X level) show that both compounds exist only as a keto tautomer, the experiment proves existence of the enol form. The difference in the results obtained by UV–Vis spectroscopy and NMR requires a deeper consideration and verification of the NMR approach, which is based on using model compounds to provide the NMR signal pattern of individual tautomers.",
author = "Silvia Hristova and Silvia Angelova and Hansen, {Poul Erik} and Liudmil Antonov",
year = "2017",
doi = "10.1016/j.dyepig.2017.03.037",
language = "English",
volume = "142",
pages = "226--229",
journal = "Dyes and Pigments",
issn = "0143-7208",
publisher = "Pergamon Press",

}

4-Carboxyl-2,6-dinitrophenylazohydroxynaphthalenes tautomerism NMR re-explained and other methods verified. / Hristova, Silvia; Angelova, Silvia; Hansen, Poul Erik; Antonov, Liudmil.

I: Dyes and Pigments, Bind 142, 2017, s. 226-229.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - 4-Carboxyl-2,6-dinitrophenylazohydroxynaphthalenes tautomerism NMR re-explained and other methods verified

AU - Hristova, Silvia

AU - Angelova, Silvia

AU - Hansen, Poul Erik

AU - Antonov, Liudmil

PY - 2017

Y1 - 2017

N2 - In two consecutive studies the tautomerism in 4-((2-hydroxynaphthalen-1-yl)diazenyl)-3,5-dinitrobenzoic acid and the structurally similar 1-((2-nitrophenyl)diazenyl)naphthalen-2-ol has been considered from viewpoint of theoretical chemistry, UV–Vis spectroscopy and NMR. Although the theoretical data (at M062X level) show that both compounds exist only as a keto tautomer, the experiment proves existence of the enol form. The difference in the results obtained by UV–Vis spectroscopy and NMR requires a deeper consideration and verification of the NMR approach, which is based on using model compounds to provide the NMR signal pattern of individual tautomers.

AB - In two consecutive studies the tautomerism in 4-((2-hydroxynaphthalen-1-yl)diazenyl)-3,5-dinitrobenzoic acid and the structurally similar 1-((2-nitrophenyl)diazenyl)naphthalen-2-ol has been considered from viewpoint of theoretical chemistry, UV–Vis spectroscopy and NMR. Although the theoretical data (at M062X level) show that both compounds exist only as a keto tautomer, the experiment proves existence of the enol form. The difference in the results obtained by UV–Vis spectroscopy and NMR requires a deeper consideration and verification of the NMR approach, which is based on using model compounds to provide the NMR signal pattern of individual tautomers.

U2 - 10.1016/j.dyepig.2017.03.037

DO - 10.1016/j.dyepig.2017.03.037

M3 - Journal article

VL - 142

SP - 226

EP - 229

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

ER -