New bis-di-organotin compounds derived from aminoacid-imine-hexadentate ligands. Multifunctional evaluation as corrosion inhibitors, antibacterials and asphaltene dispersants/inhibitors

Raúl Hernández-Altamirano, Violeta Y. Mena-Cervantes, Tomás Eduardo Chávez-Miyauchi, David Aarón Nieto-Álvarez, Marco A. Domínguez-Aguilar, Luis S. Zamudio-Rivera, Victor Barba, Francisco José Fernández-Perrino, Sandra Pérez-Miranda, Hiram I. Beltrán

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A new class of bis-di-organotin (IV) compounds were synthesized in good yields (ca. 80%) by a one-step five molecules reaction in which intervene two molecular equivalents of leucine, one of 5,5′-methylene-bis- salicylaldehyde and either two of di-n-butyltin (IV) or diphenyltin (IV) oxides, that independently provided two bis-di-organotin derivatives. The structures of these two compounds were established by 1H, 13C and 119Sn NMR, as well as by IR and elemental analysis. In both cases the 119Sn chemical shifts are characteristic of pentacoordinated atoms in solution of non-coordinating solvent (CDCl3). Once characterized, the novel compounds were tested as corrosion inhibitors at 25, 50 and 100 mg L-1 on mild steel surfaces in sour brine by linear polarization resistance and potentiodynamic curves. These experiments prove that these derivatives present top efficiencies of 54% and 68% for butyl and phenyl moieties, respectively. In addition, these two compounds were tested in vitro against Bacillus subtilis (Gram-positive, strain ATCC 6633), Escherichia coli (Gram-negative, strain DH5) and Pseudomonas fluorescens strains to assess their bactericidal activities, being more effective for the E. coli strain, at concentrations as low as 25 mg L-1. Moreover, in order to correlate different activities and ascertain homologous action mechanisms, the two derivatives were tested for their asphaltene inhibition/dispersion activity. The results suggest that the presence of the four n-butyl moieties provide the needed amphiphillic balance to obtain better efficiencies in the tested activities.
Original languageAmerican English
Pages (from-to)301-307
Number of pages270
JournalPolyhedron
DOIs
StatePublished - 22 Mar 2013
Externally publishedYes

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Organotin Compounds
organotin compound
butyltin
asphaltene
dispersant
Imines
Corrosion inhibitors
inhibitors
imines
ligand
brine
nuclear magnetic resonance
inhibitor
corrosion
polarization
steel
Ligands
oxide
Derivatives
Escherichia coli

Cite this

Hernández-Altamirano, Raúl ; Mena-Cervantes, Violeta Y. ; Chávez-Miyauchi, Tomás Eduardo ; Nieto-Álvarez, David Aarón ; Domínguez-Aguilar, Marco A. ; Zamudio-Rivera, Luis S. ; Barba, Victor ; Fernández-Perrino, Francisco José ; Pérez-Miranda, Sandra ; Beltrán, Hiram I. / New bis-di-organotin compounds derived from aminoacid-imine-hexadentate ligands. Multifunctional evaluation as corrosion inhibitors, antibacterials and asphaltene dispersants/inhibitors. In: Polyhedron. 2013 ; pp. 301-307.
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abstract = "A new class of bis-di-organotin (IV) compounds were synthesized in good yields (ca. 80{\%}) by a one-step five molecules reaction in which intervene two molecular equivalents of leucine, one of 5,5′-methylene-bis- salicylaldehyde and either two of di-n-butyltin (IV) or diphenyltin (IV) oxides, that independently provided two bis-di-organotin derivatives. The structures of these two compounds were established by 1H, 13C and 119Sn NMR, as well as by IR and elemental analysis. In both cases the 119Sn chemical shifts are characteristic of pentacoordinated atoms in solution of non-coordinating solvent (CDCl3). Once characterized, the novel compounds were tested as corrosion inhibitors at 25, 50 and 100 mg L-1 on mild steel surfaces in sour brine by linear polarization resistance and potentiodynamic curves. These experiments prove that these derivatives present top efficiencies of 54{\%} and 68{\%} for butyl and phenyl moieties, respectively. In addition, these two compounds were tested in vitro against Bacillus subtilis (Gram-positive, strain ATCC 6633), Escherichia coli (Gram-negative, strain DH5) and Pseudomonas fluorescens strains to assess their bactericidal activities, being more effective for the E. coli strain, at concentrations as low as 25 mg L-1. Moreover, in order to correlate different activities and ascertain homologous action mechanisms, the two derivatives were tested for their asphaltene inhibition/dispersion activity. The results suggest that the presence of the four n-butyl moieties provide the needed amphiphillic balance to obtain better efficiencies in the tested activities.",
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New bis-di-organotin compounds derived from aminoacid-imine-hexadentate ligands. Multifunctional evaluation as corrosion inhibitors, antibacterials and asphaltene dispersants/inhibitors. / Hernández-Altamirano, Raúl; Mena-Cervantes, Violeta Y.; Chávez-Miyauchi, Tomás Eduardo; Nieto-Álvarez, David Aarón; Domínguez-Aguilar, Marco A.; Zamudio-Rivera, Luis S.; Barba, Victor; Fernández-Perrino, Francisco José; Pérez-Miranda, Sandra; Beltrán, Hiram I.

In: Polyhedron, 22.03.2013, p. 301-307.

Research output: Contribution to journalArticle

TY - JOUR

T1 - New bis-di-organotin compounds derived from aminoacid-imine-hexadentate ligands. Multifunctional evaluation as corrosion inhibitors, antibacterials and asphaltene dispersants/inhibitors

AU - Hernández-Altamirano, Raúl

AU - Mena-Cervantes, Violeta Y.

AU - Chávez-Miyauchi, Tomás Eduardo

AU - Nieto-Álvarez, David Aarón

AU - Domínguez-Aguilar, Marco A.

AU - Zamudio-Rivera, Luis S.

AU - Barba, Victor

AU - Fernández-Perrino, Francisco José

AU - Pérez-Miranda, Sandra

AU - Beltrán, Hiram I.

PY - 2013/3/22

Y1 - 2013/3/22

N2 - A new class of bis-di-organotin (IV) compounds were synthesized in good yields (ca. 80%) by a one-step five molecules reaction in which intervene two molecular equivalents of leucine, one of 5,5′-methylene-bis- salicylaldehyde and either two of di-n-butyltin (IV) or diphenyltin (IV) oxides, that independently provided two bis-di-organotin derivatives. The structures of these two compounds were established by 1H, 13C and 119Sn NMR, as well as by IR and elemental analysis. In both cases the 119Sn chemical shifts are characteristic of pentacoordinated atoms in solution of non-coordinating solvent (CDCl3). Once characterized, the novel compounds were tested as corrosion inhibitors at 25, 50 and 100 mg L-1 on mild steel surfaces in sour brine by linear polarization resistance and potentiodynamic curves. These experiments prove that these derivatives present top efficiencies of 54% and 68% for butyl and phenyl moieties, respectively. In addition, these two compounds were tested in vitro against Bacillus subtilis (Gram-positive, strain ATCC 6633), Escherichia coli (Gram-negative, strain DH5) and Pseudomonas fluorescens strains to assess their bactericidal activities, being more effective for the E. coli strain, at concentrations as low as 25 mg L-1. Moreover, in order to correlate different activities and ascertain homologous action mechanisms, the two derivatives were tested for their asphaltene inhibition/dispersion activity. The results suggest that the presence of the four n-butyl moieties provide the needed amphiphillic balance to obtain better efficiencies in the tested activities.

AB - A new class of bis-di-organotin (IV) compounds were synthesized in good yields (ca. 80%) by a one-step five molecules reaction in which intervene two molecular equivalents of leucine, one of 5,5′-methylene-bis- salicylaldehyde and either two of di-n-butyltin (IV) or diphenyltin (IV) oxides, that independently provided two bis-di-organotin derivatives. The structures of these two compounds were established by 1H, 13C and 119Sn NMR, as well as by IR and elemental analysis. In both cases the 119Sn chemical shifts are characteristic of pentacoordinated atoms in solution of non-coordinating solvent (CDCl3). Once characterized, the novel compounds were tested as corrosion inhibitors at 25, 50 and 100 mg L-1 on mild steel surfaces in sour brine by linear polarization resistance and potentiodynamic curves. These experiments prove that these derivatives present top efficiencies of 54% and 68% for butyl and phenyl moieties, respectively. In addition, these two compounds were tested in vitro against Bacillus subtilis (Gram-positive, strain ATCC 6633), Escherichia coli (Gram-negative, strain DH5) and Pseudomonas fluorescens strains to assess their bactericidal activities, being more effective for the E. coli strain, at concentrations as low as 25 mg L-1. Moreover, in order to correlate different activities and ascertain homologous action mechanisms, the two derivatives were tested for their asphaltene inhibition/dispersion activity. The results suggest that the presence of the four n-butyl moieties provide the needed amphiphillic balance to obtain better efficiencies in the tested activities.

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