9-Methylcaffeinium iodide, a bio-based salt obtained by reaction of caffeine with methyl iodide, is an imidazolium salt. The electrochemical behaviour of 9-methylcaffeinium iodide was studied by means of cyclic voltammetry, differential pulse voltammetry and electrolysis. Its behaviour revealed to be very similar to that of common imidazolium salts. In fact, its cathodic reduction yielded the corresponding N-heterocyclic carbene, which was evidenced by its reaction products with dioxygen and with sulfur, although in low amounts. In fact, this electrogenerated carbene was very unstable and prone to add water, yielding a ring opening product (hymeniacidin) in high yield. Hymeniacidin is a natural product from the marine sponge Hymeniacidon sp. The voltammetric behaviour of isolated hymeniacidin confirmed the in situ formation of this ring opening product, by comparison of the voltammetric peak potentials of starting caffeinium salt and hymeniacidin. This study allowed to determine that hymeniacidin derives from NHC, and not by hydrolysis of the caffeinium salt.

Electrochemical behaviour of 9-methylcaffeinium iodide and in situ electrochemical synthesis of hymeniacidin / Pandolfi, Fabiana; Mattiello, Leonardo; Zane, Daniela; Feroci, Marta. - In: ELECTROCHIMICA ACTA. - ISSN 0013-4686. - STAMPA. - 280:(2018), pp. 71-76. [10.1016/j.electacta.2018.05.073]

Electrochemical behaviour of 9-methylcaffeinium iodide and in situ electrochemical synthesis of hymeniacidin

Pandolfi, Fabiana
Membro del Collaboration Group
;
Mattiello, Leonardo
Membro del Collaboration Group
;
Zane, Daniela
Membro del Collaboration Group
;
Feroci, Marta
Membro del Collaboration Group
2018

Abstract

9-Methylcaffeinium iodide, a bio-based salt obtained by reaction of caffeine with methyl iodide, is an imidazolium salt. The electrochemical behaviour of 9-methylcaffeinium iodide was studied by means of cyclic voltammetry, differential pulse voltammetry and electrolysis. Its behaviour revealed to be very similar to that of common imidazolium salts. In fact, its cathodic reduction yielded the corresponding N-heterocyclic carbene, which was evidenced by its reaction products with dioxygen and with sulfur, although in low amounts. In fact, this electrogenerated carbene was very unstable and prone to add water, yielding a ring opening product (hymeniacidin) in high yield. Hymeniacidin is a natural product from the marine sponge Hymeniacidon sp. The voltammetric behaviour of isolated hymeniacidin confirmed the in situ formation of this ring opening product, by comparison of the voltammetric peak potentials of starting caffeinium salt and hymeniacidin. This study allowed to determine that hymeniacidin derives from NHC, and not by hydrolysis of the caffeinium salt.
9-Methylcaffeinium iodide; Cyclic voltammetry; Differential pulse voltammetry; Electrochemical reduction; Hymeniacidin; Chemical Engineering (all); Electrochemistry
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Electrochemical behaviour of 9-methylcaffeinium iodide and in situ electrochemical synthesis of hymeniacidin / Pandolfi, Fabiana; Mattiello, Leonardo; Zane, Daniela; Feroci, Marta. - In: ELECTROCHIMICA ACTA. - ISSN 0013-4686. - STAMPA. - 280:(2018), pp. 71-76. [10.1016/j.electacta.2018.05.073]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1111464
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