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Addition of tryptophan methyl-ester on [60]fullerene: theoretical investigation of the mechanisms of azomethine ylides and fulleropyrrolidine formation

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Abstract

In this paper, we perform the synthesization of carbon nanoparticles for active principle vectorization, with the suggestion of a reaction mechanism of tryptophan methyl ester addition on [60]fullerene. Firstly, we studied the effect of tryptophan form on its addition reaction on [60]fullerene. So, in order to determine the preferred environment that makes this reaction the most favorable, we considered all tryptophan possible forms in our investigation: the molecular, the zwitterionic, and the dibasic forms. Secondly, we investigate the proposed reaction mechanism of tryptophan methyl ester addition on [60]fullerene using theoretical thermodynamic calculation. Our hypothesis suggests the formation of azomethine ylide molecule in a first step followed by its addition on [60]fullerene in the second step by the photo-addition reaction involving the oxygen in its singlet state. The stability of each reactive intermediate involved in this mechanism is verified thermodynamically. The 12 most stable conformations of azomethine ylide were observed through potential energy surface analysis. They were obtained by a relaxed scan of the four dihedral angles. The calculations were conducted on the optimized geometry of fulleropyrrolidine mono-adduct and the bulk values of its thermodynamic constants were also determined. Infrared spectra observed in 100–4000 cm−1 region confirmed our hypothesis suggesting the first step of azomethine ylide formation followed by the second step of azomethine ylide addition on [60]fullerene by ν(Caliphatic-C-N), ν(Caromatic-C-N) and δ(N-H) coupled with ν(C-N) absorption bond.

Optimized geometry of the Fulleropyrrolidine monoaduct molecule.

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Acknowledgements

The authors would like to thank the Laboratory of Materials, Molecules, and Applications (LMMA, Tunis) for the research fellowship and the laboratory of studies of technical and analytical molecular instruments (LETIAM, Paris) for the collaboration.

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Authors and Affiliations

  1. Laboratoire Matériaux, Molécules et Applications, Institut Préparatoire aux Etudes Scientifiques et Techniques, La Marsa, 2071, Université de Carthage, Carthage, Tunisie

    Nabil Omri, Noura Khemiri, Manef Abderrabba & Sabri Messaoudi

  2. LETIAM, Groupe de Chimie Analytique de Paris Sud, EA 4041, IUT d’Orsay, Université Paris Sud 11, Plateau de Moulon, 91400, Orsay, France

    Fathi Moussa

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  1. Nabil Omri
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  2. Noura Khemiri
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  4. Fathi Moussa
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  5. Sabri Messaoudi
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Correspondence to Nabil Omri.

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Omri, N., Khemiri, N., Abderrabba, M. et al. Addition of tryptophan methyl-ester on [60]fullerene: theoretical investigation of the mechanisms of azomethine ylides and fulleropyrrolidine formation. J Mol Model 24, 270 (2018). https://doi.org/10.1007/s00894-018-3760-2

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