Studies of the complexation behavior of tetramorpholinylo-PNP-lariat ether with Ag(<scp>i</scp>), Ca(<scp>ii</scp>), Cd(<scp>ii</scp>), Cu(<scp>ii</scp>) and Pb(<scp>ii</scp>) using Electrospray Ionization Mass Spectrometry

Gutowska, Natalia; Pasternak, Beata; Seliger, Piotr; Andrijewski, Grzegorz

doi:10.1039/c4nj01904k

Cited by 9 publications

(7 citation statements)

References 73 publications

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“…Furthermore, the interaction is probably strengthened by additional stabilization by oxygen atoms from crown ether moiety (there is no cleavage of the macrocycle skeleton under the influence of the applied voltage during the experiment). Similar fragmentation pathways were also noticed in previous studies of these complexes with morpholinyl and piperidinyl substituents [35,36].…”

Section: Mass Spectrometry Investigations Of Ligand and Its Complexessupporting

confidence: 87%

“…Furthermore, silver ion in the AgL complex is preferably attracted to nitrogen atoms from substituents which are attached to the exocyclic phosphorus atom. In the previously described PNP lariat ethers derivatives, binding of the first silver ion was realized by the endocyclic nitrogen atom from the cyclotriphosphazene subunit [30][31][32][33][34][35][36]. The second silver ion is bound by the endocyclic nitrogen atom of the cyclotriphosphazene ring.…”

Section: Discussionmentioning

confidence: 99%

“…These studies show that changes of substituents, as well as solvents used during the complexation process, affect the formation of the various structures of the complexes, especially with silver (I) cation. The studies for other cations comprise of the complexing behavior of PNP-lariat ether with other metal cations (Cd 2+ , Cu 2+ , Ca 2+ , and Pb 2+ ) using ESI-MS and MS/MS techniques [35,36]. Macrocyclic derivatives of cyclotriphosphazene and their complexes were found to reveal antitumor activity as well as anti-AIDS activity [37][38][39].…”

Section: Introductionmentioning

confidence: 99%

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Mass Spectrometry Reveals Complexing Properties of Modified PNP-Lariat Ether Containing Benzyl Derivative of (S)–Prolinamine

et al. 2019

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In the investigation presented here the synthesis of new lariat ether derivative obtained from the modification of tetrapyrrolidinyl-PNP-crown ether macrocycle is described. The polyheterotopic molecular coreceptor consisted of the replacement of chlorine atoms with an optically active (S)-(1-benzylpyrrolidin-2-yl) methanamine. The structure was confirmed by using elemental analysis, mass spectrometry, and NMR spectroscopy. This work covers results concerning the complexing properties of the new ligand towards Ag + , Cu 2+, Co 2+, Ni 2+ , and Zn 2+ ions. The formation of non-covalent complexes of 1:1 stoichiometry with the Cu 2+, Co 2+, Ni 2+ , and Zn 2+ ions have been confirmed by mass spectrometry. Due to the previous work and application possibilities, a large emphasis was put on the investigation of the complexation ability of lariat ether with silver (I) cation to determine stability constants by direct potentiometric method. In this case, the formation of four different forms of complexes AgL, Ag 2 L, Ag 3 L, and Ag 4 L has been proved. The observed unusual binding through the nitrogen atoms from the exocyclic substituents may provide the structural unit to build a new coordination polymers.Molecules 2020, 25, 136 2 of 19 the preparation of the number of crown ethers, which can be used in various applications such as classical (polymer-supported catalysts PTC, reagents for separation and extraction, etc.) and highly sophisticated (the redox switches for membrane transport, synthetic cation-conducting channels, nucleotide-based molecular boxes and enzyme mimics) [7][8][9][10][11][12]. There are three known main types of lariat ethers: C-pivot lariat ethers [13][14][15], where the side arm is attached to the carbon atom, N-pivot lariat ethers [16][17][18], and finally P-pivot lariat ethers [19,20].The subjects of this research are the P-pivot lariat ether derivatives. The versatile precursors for this type of P-pivot lariat ethers have been obtained by the reaction of hexachlorocyclotriphosphazene with tetraethylene glycol in the presence of sodium hydride (Scheme 1).Molecules 2019, 24, x 2 of 19 various applications such as classical (polymer-supported catalysts PTC, reagents for separation and extraction, etc.) and highly sophisticated (the redox switches for membrane transport, synthetic cation-conducting channels, nucleotide-based molecular boxes and enzyme mimics) [7][8][9][10][11][12]. There are three known main types of lariat ethers: C-pivot lariat ethers [13][14][15], where the side arm is attached to the carbon atom, N-pivot lariat ethers [16][17][18], and finally P-pivot lariat ethers [19,20]. The subjects of this research are the P-pivot lariat ether derivatives. The versatile precursors for this type of P-pivot lariat ethers have been obtained by the reaction of hexachlorocyclotriphosphazene with tetraethylene glycol in the presence of sodium hydride (Scheme 1). Scheme 1. Formation of different types of macrocyclic compounds from hexachlorocyclotriphosphazene substrate. Scheme 1. Formation of dif...

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Section: Mass Spectrometry Investigations Of Ligand and Its Complexessupporting

confidence: 87%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mass Spectrometry Reveals Complexing Properties of Modified PNP-Lariat Ether Containing Benzyl Derivative of (S)–Prolinamine

et al. 2019

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“…Similar sandwich complex for macrocyclic Ag(I) systems were reported in the literature on the basis of potentiometric as well as mass spectrometric measurements. 19,26,27 Schematic presentation of the sandwich like complex is presented on figure S13 in SI. Although in the ESI-MS spectra there is no signal for the original sandwich complexes, in the spectrum within the region above m/z = 600 we can notice two signal pairs at m/z 691-693 and 891-893…”

Section: Resultsmentioning

confidence: 99%

Investigation on silver complexes of novel 1,2,3-triazole linked crown ethers by NMR analysis

et al. 2015

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The novel derivatives of 1,2,3-triazole linked crown ethers were investigated towards silver(I) ion coordination. The NMR measurements in deuterated methanol in different ratios of ligand and silver cation were studied. The experiments were performed in order to examine the way of binding Ag(I) ion by the selected ligands. The results are presented for complexes with the Ag:L stoichiometry 0.5:1, 1:1 and 2:1, respectively. Depending on the type of crown ether moiety incorporated into the macrocyclic skeleton, interesting differences in the mode of stepwise coordination of the ion were noticed.

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“…Nitrogen heterocycles are intensely studied chelating ligands, and a number of complexes with pyridyl‐related ligands have been studied by ESI‐MS/MS methods . Collision activation experiments were used to characterize the stability of aza metal complexes with silver …”

Section: Introductionmentioning

confidence: 99%

Electrospray mass spectrometry and molecular modeling study of formation and stability of silver complexes with diazaperylene and bisisoquinoline

et al. 2018

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The complex formation of the following diazaperylene ligands (L) 1,12-diazaperylene 1, 1,1'-bisisoquinoline 2, 2,11-disubstituted 1,12-diazaperylenes (alkyl = methyl, ethyl, isopropyl, 3, 5, 7), 3,3'-disubstituted 1,1'-bisisoquinoline (alkyl = methyl, ethyl, isopropyl, 4, 6, 8 and with R = phenyl, 11 and with pyridine 12), and the 5,8-dimethoxy-substituted diazaperylene 9, 6,6'-dimethoxy-substituted bisisoquinoline 10 with AgBF4 was investigated. Collision-induced dissociation measurements were used to evaluate the relative stabilities of the ligands themselves and for the [1:1] complexes as well as for the homoleptic and heteroleptic silver [1:2] complexes in the gas phase. This method is very useful in rapid screening of the stabilities of new complexes in the gas phase. The influence of the spatial arrangement of the ligands and the type of substituents employed for the complexation were examined. The effect of the preorganization of the diazaperylene on the threshold activation voltages and thus of the relative binding energies of the different complexes are discussed. Density functional theory calculations were used to calculate the optimized structures of the silver complexes and compared with the stabilities of the complexes in the gas phase for the first time.

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Studies of the complexation behavior of tetramorpholinylo-PNP-lariat ether with Ag(i), Ca(ii), Cd(ii), Cu(ii) and Pb(ii) using Electrospray Ionization Mass Spectrometry

Abstract: The identification of complexes containing PNP-lariat ether with Ag(i), Ca(ii), Cu(ii), Cd(ii) and Pb(ii) by ESI-MS technique is presented. The tandem mass spectra of these complexes were done in order to evaluate the stability of the different types of the complexes formed.

Cited by 9 publications

References 73 publications

Mass Spectrometry Reveals Complexing Properties of Modified PNP-Lariat Ether Containing Benzyl Derivative of (S)–Prolinamine

Mass Spectrometry Reveals Complexing Properties of Modified PNP-Lariat Ether Containing Benzyl Derivative of (S)–Prolinamine

Investigation on silver complexes of novel 1,2,3-triazole linked crown ethers by NMR analysis

Electrospray mass spectrometry and molecular modeling study of formation and stability of silver complexes with diazaperylene and bisisoquinoline

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