Chemical Papers

, Volume 71, Issue 10, pp 2011–2022 | Cite as

X-ray diffraction and relativistic DFT studies on the molecular biomarker fac-Re(CO)3(4,4′-dimethyl-2,2′-bpy)(E-2-((3-amino-pyridin-4-ylimino)-methyl)-4,6-di-tert-butylphenol)(PF6)

  • Alexander Carreño
  • Manuel Gacitúa
  • Elies Molins
  • Ramiro Arratia-Pérez
S.I. : Coordination and Bioinorganic Conference


The fac-[Re(CO)3(4,4′-dimethyl-2,2′-bpy)L]PF6 (C2) complex have been recently reported as a useful fluorophore for walled cells (yeasts and bacteria) without the need of antibodies. In the present work, we report the structural parameters of the C2 complex, where L is an ancillary ligand E-2-((3-amino-pyridin-4-ylimino)-methyl)-4,6-di-tert-butylphenol, which presents an intramolecular hydrogen bond (IHB). The C2 crystals were obtained by slow evaporation of a dichloromethane solution, yielding yellow blocks. The crystal structure solution of the complex C2 showed a monoclinic crystal system and discrete organometallic cations and PF6 as the counter ion, with partially occupation of solvent molecules (CH2Cl2). The complex C2 having a fac-geometry of the three carbonyl ligands, possesses the following bond distances Re–C(CO): Re1–C24, 1.87(8) Å; Re1–C25, 1.58(12) Å and Re1–C26, 1.90(8) Å. The distorted octahedral geometry observed in the C2 structure is due to the C(CO)–Re1–N1(imine) angle for the three carbonyls that are significantly different. The Re–N1 bond distance of 2.16(4) Å corresponds to the nitrogen coordination of the pyridine fragment of the ancillary ligand L, completing the octahedral geometry. Here we complement the C2 descriptions due to the considerable biological interest of its use as d6 metal fluorophore in walled cells (i.e., yeast and bacteria). DFT calculations were performed including scalar and spin–orbit (SO) relativistic effects with agree often reasonably well with experimental X-ray data. Through frequency calculations we estimated the strength of the intramolecular hydrogen bond (with a OH···N distance of 2.621 Å) accounting for near 40 kcal/mol, indicating that is a strong hydrogen bond which contributes to the molecular stability. In addition, we observed the L electron-withdrawing effect on the rhenium core. The agreement between the observed and computed bond distances and angles brings confidence on the choice of the computed models and level of theory. These kind of Rhenium (I) complexes designed to develop novel fluorophores suitable for biological applications.


Rhenium tricarbonyl complexes Schiff base Relativistic DFT 



Funded partially by project RC120001 of the Iniciativa Científica Milenio del Ministerio de Economía, Fomento y Turismo del Gobierno de Chile and Nucleo UNAB DI-1419-16/N; E. Molins acknowledges funding by the Spanish Ministerio de Economía y Competividad (ENE2015-63969 and SEV2015-0496). We thank Dr. Dayan Paez-Hernandez (UNAB) for relativistic DFT calculations; Dr. Ivonne Chavez (Departamento de Química Inorgánica, Pontificia Universidad Católica de Chile) for instrumentals facilities, Dr. Juan A. Fuentes (Laboratorio de Genética y Patogénesis Bacteriana, Facultad de Ciencias Biológicas, UNAB) for biological contributions and B.A. Alfonso Inzunza G. for his help with the English translation.

Supplementary material

11696_2017_196_MOESM1_ESM.docx (522 kb)
Supporting Information: CCDC 1448327 contains the supplementary crystallographic data for C2. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via (DOCX 522 kb)


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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2017

Authors and Affiliations

  1. 1.Center of Applied Nanosciences (CENAP)Universidad Andres BelloSantiagoChile
  2. 2.Núcleo Milenio de Ingeniería Molecular para Catálisis y Biosensores (MECB), ICMSantiagoChile
  3. 3.Facultad de Quimica y BiologiaUSACHSantiagoChile
  4. 4.Institut de Ciència de Materials de Barcelona (ICMAB-CSIC)BarcelonaSpain

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