The synthesis and characterization of the ferrocenyl methylhydantoin 5-ferrocenyl-5-methylimidazolidine-2,4-dione, efficiently prepared through a Bucherer-Bergs reaction, and its derivatives carrying tert-butoxycarbonyl (Boc) protecting groups, namely 1,3-bis(tert-butoxycarbonyl)-5-ferrocenyl-S-methylirnidazolidine-2,4-dione and 1-(tert-butoxycarbonyl)-5-ferrocenyl-5-methylimidazolidine-2,4-dione, are reported. X-ray diffraction and ESI-mass spectrometry analyses of the ferrocenyl methylhydantoin revealed the presence of C=O center dot center dot center dot H-N intermolecularly hydrogen-bonded dimers. The mono-Boc derivative formed a hydrogen-bonded dimer in solution, as confirmed by H-1 NMR, FT-IR, and cyclic voltammetry experiments at different concentrations in CDCl3 or CHCl3.

Hydrogen-bond-assisted, concentration-dependent molecular dimerization of ferrocenyl hydantoins

Bisello, Annalisa
Membro del Collaboration Group
;
Cardena, Roberta
Membro del Collaboration Group
;
Crisma, Marco
Membro del Collaboration Group
;
Formaggio, Fernando
Membro del Collaboration Group
;
Santi, Saverio
Membro del Collaboration Group
2017

Abstract

The synthesis and characterization of the ferrocenyl methylhydantoin 5-ferrocenyl-5-methylimidazolidine-2,4-dione, efficiently prepared through a Bucherer-Bergs reaction, and its derivatives carrying tert-butoxycarbonyl (Boc) protecting groups, namely 1,3-bis(tert-butoxycarbonyl)-5-ferrocenyl-S-methylirnidazolidine-2,4-dione and 1-(tert-butoxycarbonyl)-5-ferrocenyl-5-methylimidazolidine-2,4-dione, are reported. X-ray diffraction and ESI-mass spectrometry analyses of the ferrocenyl methylhydantoin revealed the presence of C=O center dot center dot center dot H-N intermolecularly hydrogen-bonded dimers. The mono-Boc derivative formed a hydrogen-bonded dimer in solution, as confirmed by H-1 NMR, FT-IR, and cyclic voltammetry experiments at different concentrations in CDCl3 or CHCl3.
2017
File in questo prodotto:
File Dimensione Formato  
Manuscript_28_03_2017.pdf

Open Access dal 18/05/2018

Tipologia: Preprint (submitted version)
Licenza: Accesso libero
Dimensione 379.27 kB
Formato Adobe PDF
379.27 kB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11577/3249537
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 5
  • ???jsp.display-item.citation.isi??? 4
  • OpenAlex ND
social impact