A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols

Silvia Hristova, V Deneva, Michael Pittelkow, Aurelien Crochet, Fadhil S. Kamounah, Katharina M. Fromm, Poul Erik Hansen, Liudmil Antonov

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties of the substituent. The implementation of a sidearm in 3 creates a condition for competition between the nitrogen from the azo group and from the piperidine unit for the tautomeric proton. In this case the use of acid as a stimulus for controlling the tautomeric process was achieved.
OriginalsprogEngelsk
TidsskriftDyes and Pigments
Vol/bind156
Udgave nummerSeptember
Sider (fra-til)91-99
Antal sider9
ISSN0143-7208
DOI
StatusUdgivet - 1 mar. 2018

Emneord

  • Tautomerism
  • azo dyes

Citer dette

Hristova, S., Deneva, V., Pittelkow, M., Crochet, A., Kamounah, F. S., Fromm, K. M., ... Antonov, L. (2018). A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols. Dyes and Pigments, 156(September), 91-99. https://doi.org/10.1016/j.dyepig.2018.03.070
Hristova, Silvia ; Deneva, V ; Pittelkow, Michael ; Crochet, Aurelien ; Kamounah, Fadhil S. ; Fromm, Katharina M. ; Hansen, Poul Erik ; Antonov, Liudmil . / A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols. I: Dyes and Pigments. 2018 ; Bind 156, Nr. September. s. 91-99.
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title = "A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols",
abstract = "A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties of the substituent. The implementation of a sidearm in 3 creates a condition for competition between the nitrogen from the azo group and from the piperidine unit for the tautomeric proton. In this case the use of acid as a stimulus for controlling the tautomeric process was achieved.",
keywords = "Tautomerism, azo dyes, proton transfer, Dyes",
author = "Silvia Hristova and V Deneva and Michael Pittelkow and Aurelien Crochet and Kamounah, {Fadhil S.} and Fromm, {Katharina M.} and Hansen, {Poul Erik} and Liudmil Antonov",
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Hristova, S, Deneva, V, Pittelkow, M, Crochet, A, Kamounah, FS, Fromm, KM, Hansen, PE & Antonov, L 2018, 'A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols', Dyes and Pigments, bind 156, nr. September, s. 91-99. https://doi.org/10.1016/j.dyepig.2018.03.070

A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols. / Hristova, Silvia ; Deneva, V; Pittelkow, Michael ; Crochet, Aurelien ; Kamounah, Fadhil S.; Fromm, Katharina M. ; Hansen, Poul Erik; Antonov, Liudmil .

I: Dyes and Pigments, Bind 156, Nr. September, 01.03.2018, s. 91-99.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols

AU - Hristova, Silvia

AU - Deneva, V

AU - Pittelkow, Michael

AU - Crochet, Aurelien

AU - Kamounah, Fadhil S.

AU - Fromm, Katharina M.

AU - Hansen, Poul Erik

AU - Antonov, Liudmil

PY - 2018/3/1

Y1 - 2018/3/1

N2 - A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties of the substituent. The implementation of a sidearm in 3 creates a condition for competition between the nitrogen from the azo group and from the piperidine unit for the tautomeric proton. In this case the use of acid as a stimulus for controlling the tautomeric process was achieved.

AB - A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties of the substituent. The implementation of a sidearm in 3 creates a condition for competition between the nitrogen from the azo group and from the piperidine unit for the tautomeric proton. In this case the use of acid as a stimulus for controlling the tautomeric process was achieved.

KW - Tautomerism

KW - azo dyes

KW - proton transfer

KW - Dyes

U2 - 10.1016/j.dyepig.2018.03.070

DO - 10.1016/j.dyepig.2018.03.070

M3 - Journal article

VL - 156

SP - 91

EP - 99

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

IS - September

ER -

Hristova S, Deneva V, Pittelkow M, Crochet A, Kamounah FS, Fromm KM et al. A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols. Dyes and Pigments. 2018 mar 1;156(September):91-99. https://doi.org/10.1016/j.dyepig.2018.03.070