Formation of intramolecular hydrogen bonds in heterodisubstituted ferrocene diamides with a secondary and a tertiary amido group: X-ray structure of 1′-(N′-butyl-carbamoyl)-morpholino ferrocenecarboxamide

Árpád Kuik, R. Skoda-Földes, A. Bényei, Gábor Rangits, L. Kollár

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Various unsymmetrically substituted ferrocene 1,1′-diamides have been synthesized via homogeneous catalytic carbonylation starting from 1,1′-diiodoferrocene. The unique features observed in the 1H NMR and IR spectra of the compounds bearing a secondary and a tertiary amido group are explained by the formation of an internal hydrogen bond between the substituents. Addition of chloride ions (as a tetrabutylammonium salt) into the solutions of these compounds results in spectroscopic changes due to the formation of intermolecular hydrogen bonds between the ferrocene diamide and the anion. The solid state structure of 1′-(N′-butyl-carbamoyl)-morpholino ferrocenecarboxamide (1a) has also been determined by X-ray crystallography. A strong intramolecular H-bond between the NH group of the N′-butyl-carbamoyl moiety and the CO of the tertiary amido group was observed.

Original languageEnglish
Pages (from-to)3037-3042
Number of pages6
JournalJournal of Organometallic Chemistry
Volume691
Issue number13
DOIs
Publication statusPublished - Jun 15 2006

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Diamide
Morpholinos
Hydrogen
Hydrogen bonds
Bearings (structural)
X-Rays
hydrogen bonds
Carbonylation
X rays
X ray crystallography
X Ray Crystallography
Carbon Monoxide
Anions
Chlorides
x rays
Negative ions
Salts
Nuclear magnetic resonance
Ions
crystallography

Keywords

  • Carbonylation
  • Diamides
  • Ferrocene
  • Intramolecular hydrogen bond
  • Palladium

ASJC Scopus subject areas

  • Chemical Engineering (miscellaneous)
  • Materials Science (miscellaneous)
  • Materials Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Biochemistry

Cite this

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title = "Formation of intramolecular hydrogen bonds in heterodisubstituted ferrocene diamides with a secondary and a tertiary amido group: X-ray structure of 1′-(N′-butyl-carbamoyl)-morpholino ferrocenecarboxamide",
abstract = "Various unsymmetrically substituted ferrocene 1,1′-diamides have been synthesized via homogeneous catalytic carbonylation starting from 1,1′-diiodoferrocene. The unique features observed in the 1H NMR and IR spectra of the compounds bearing a secondary and a tertiary amido group are explained by the formation of an internal hydrogen bond between the substituents. Addition of chloride ions (as a tetrabutylammonium salt) into the solutions of these compounds results in spectroscopic changes due to the formation of intermolecular hydrogen bonds between the ferrocene diamide and the anion. The solid state structure of 1′-(N′-butyl-carbamoyl)-morpholino ferrocenecarboxamide (1a) has also been determined by X-ray crystallography. A strong intramolecular H-bond between the NH group of the N′-butyl-carbamoyl moiety and the CO of the tertiary amido group was observed.",
keywords = "Carbonylation, Diamides, Ferrocene, Intramolecular hydrogen bond, Palladium",
author = "{\'A}rp{\'a}d Kuik and R. Skoda-F{\"o}ldes and A. B{\'e}nyei and G{\'a}bor Rangits and L. Koll{\'a}r",
year = "2006",
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TY - JOUR

T1 - Formation of intramolecular hydrogen bonds in heterodisubstituted ferrocene diamides with a secondary and a tertiary amido group

T2 - X-ray structure of 1′-(N′-butyl-carbamoyl)-morpholino ferrocenecarboxamide

AU - Kuik, Árpád

AU - Skoda-Földes, R.

AU - Bényei, A.

AU - Rangits, Gábor

AU - Kollár, L.

PY - 2006/6/15

Y1 - 2006/6/15

N2 - Various unsymmetrically substituted ferrocene 1,1′-diamides have been synthesized via homogeneous catalytic carbonylation starting from 1,1′-diiodoferrocene. The unique features observed in the 1H NMR and IR spectra of the compounds bearing a secondary and a tertiary amido group are explained by the formation of an internal hydrogen bond between the substituents. Addition of chloride ions (as a tetrabutylammonium salt) into the solutions of these compounds results in spectroscopic changes due to the formation of intermolecular hydrogen bonds between the ferrocene diamide and the anion. The solid state structure of 1′-(N′-butyl-carbamoyl)-morpholino ferrocenecarboxamide (1a) has also been determined by X-ray crystallography. A strong intramolecular H-bond between the NH group of the N′-butyl-carbamoyl moiety and the CO of the tertiary amido group was observed.

AB - Various unsymmetrically substituted ferrocene 1,1′-diamides have been synthesized via homogeneous catalytic carbonylation starting from 1,1′-diiodoferrocene. The unique features observed in the 1H NMR and IR spectra of the compounds bearing a secondary and a tertiary amido group are explained by the formation of an internal hydrogen bond between the substituents. Addition of chloride ions (as a tetrabutylammonium salt) into the solutions of these compounds results in spectroscopic changes due to the formation of intermolecular hydrogen bonds between the ferrocene diamide and the anion. The solid state structure of 1′-(N′-butyl-carbamoyl)-morpholino ferrocenecarboxamide (1a) has also been determined by X-ray crystallography. A strong intramolecular H-bond between the NH group of the N′-butyl-carbamoyl moiety and the CO of the tertiary amido group was observed.

KW - Carbonylation

KW - Diamides

KW - Ferrocene

KW - Intramolecular hydrogen bond

KW - Palladium

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