The Phosphoryl and the Carbonyl Group as Hydrogen Bond Acceptors

Modro, Agnes M.; Modro, Tomasz A.

doi:10.1080/10426500213336

Cited by 8 publications

(7 citation statements)

References 2 publications

(1 reference statement)

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“…These shifts suggest that the phosphoryl group interacts via hydrogen bonds with carboxylic groups and/or ammonium groups of the polymer matrix. Our P=O shifts are close to the literature value (Δυ P=O = −26 cm −1 ) described in the case of diethyl phosphonate motifs involved in hydrogen bonds [ 50 ]. Only one carbonyl band is observed in the IR spectrum; ν C=O COOH (host) and ν C=O imide (guest) bands being superimposed, no clear conclusion could be drawn regarding the non-covalent interactions between carbonyl groups and hydrogen bonding donor/acceptor groups.…”

Section: Resultssupporting

confidence: 89%

A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix

et al. 2013

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New host-guest materials have been prepared by incorporation of a home-made organic probe displaying a pyrene motif and a phosphonate function into a regular amphiphilic copolymer. Using powder X-Ray diffraction, photoluminescence and FT-IR spectroscopy, we have been able to study the non-covalent interactions between the host matrix and the guest molecule in the solid state. Interestingly, we have shown that the matrix directs the guest spatial localization and alters its properties. Thanks to the comparison of pyrene vs. N-pyrenylmaleimide derivatives, the influence of the chemical nature of the guest molecules on the non-covalent interactions with the host have been studied. In addition, using polyethylene glycol as a reference host, we have been able to evidence a true matrix effect within our new insertion materials. The phosphonated guest molecule appears to be a novel probe targeting the hydrophilic domain of the host copolymer.

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Section: Resultssupporting

confidence: 89%

A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix

et al. 2013

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“…The IR band of the PdO moiety showed almost no shift despite its involvement in hydrogen bonding. 22 In an FTIR study of hydrogen bonding in poly(alkylene phosphate)s, the PdO stretch was at 1218 cm -1 , the (P)O-C stretch was at 1058 cm -1 , and bands at 890 and 816 cm -1 were assigned to the asymmetrical and symmetrical P-O(C) stretching vibrations, respectively, both of which are relatively weak. 23 As the temperature was increased, the extent of hydrogen bonding decreased, but the effect on the position of the IR bands was negligible until the temperature was close to the melting point.…”

Section: Discussionmentioning

confidence: 99%

Bifunctional Coordinating Polymers: Auxiliary Groups as a Means of Tuning the Ionic Affinity of Immobilized Phosphate Ligands

Alexandratos

Zhu

2005

Macromolecules

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A series of coordinating polymers are synthesized by immobilizing polyols (ethylene glycol, glycerol, 1,1,1-tris(hydroxymethyl)ethane, pentaerythritol, and pentaerythritol triethoxylate) onto cross-linked poly(vinylbenzyl chloride) and then monosubstituting with diethyl phosphate ligands. Ionic affinities are determined with a series of divalent transition metal ions: Pb2+, Cd2+, Cu2+, Ni2+, and Zn2+. For each polymer, the variable controlling the affinity, as measured by the distribution coefficient, D, is the polarizability of the transition metal ion, as measured by the Misono softness parameter, σ. For D ≥ 0, the correlation is D = Sσ + σmin, where S is the selectivity and σmin is the minimum softness of a divalent transition metal ion which must be exceeded for coordination to occur. The values of S are 3810 (pentaerythritol), 1480 (pentaerythritol triethoxylate), 1340 (glycerol), 474 (tris(hydroxymethyl)ethane), and 21 (glycol); increasing S indicates greater selectivity. It is proposed that, though coordination occurs through the phosphate ligand, selectivity varies as a function of the polyol: the −OH groups act as auxiliary groups in modifying the polarizability of the phosphate ligands (the primary ligand) through hydrogen bonding and, as a result, affecting the selectivity of the primary ligand. Interaction between the −OH and phosphate moieties is evident in FTIR spectra of the polymers with the absorbance of a band within the range 874−895 cm-1.

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“…The shifting of 3-OH is likely due to hydrogen bonding with the oxygen atom from the Au−P−O − group. 54,58,59 Additionally, the shifting of the A-ring hydrogen atoms could be an indication that the ring was close enough for an interaction with the gold center. 60−63 Although 14 could be readily characterized by HRMS, the estrogen adduct did not survive the electrospray conditions.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of Spirocyclic Diphosphite-Supported Gold Metallomacrocycles via a Protodeauration/Cyclization Strategy: Mechanistic and Binding Studies

et al. 2018

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A spirocylic diphosphite was used to generate P-metalated bimetallic complexes through protodeauration reactions involving LAuCHBu (L = JohnPhos, BuXPhos) and metallomacrocycles through protodeauration/cyclization usingBuCHAuP^PAuCHBu precursors (P^P = flexible diphosphine). While the synthesis of the bimetallic complexes followed a stepwise process, generation of the metallomacrocycles was highly complex because of a series of reversible ligand redistribution reactions. The self-assembly was monitored, and key intermediates were identified by NMR spectroscopy and high-resolution mass spectrometry. The mechanistic investigation showed that using flexible diphosphine linkers was critical to the selective synthesis of metallomacrocycles because rigid diphosphines generated intractable mixtures of linear and cyclic compounds. The X-ray structure of a 32-membered metallomacrocycle revealed that the compound crystallized in an unsymmetrical collapsed form that was held together by two supported aurophilic interactions while the flexible diphosphines were folded along opposite sides of the metallomacrocycle. The solution structure was consistent with a symmetric species, which suggested interconversion between an open and collapsed form and/or rapid twisting of a collapsed form. The 32-membered metallomacrocycle was used to bind estrogen primarily through the formation of AuP-O···H-OR hydrogen bonds.

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The Phosphoryl and the Carbonyl Group as Hydrogen Bond Acceptors

Cited by 8 publications

References 2 publications

A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix

A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix

Bifunctional Coordinating Polymers: Auxiliary Groups as a Means of Tuning the Ionic Affinity of Immobilized Phosphate Ligands

Synthesis of Spirocyclic Diphosphite-Supported Gold Metallomacrocycles via a Protodeauration/Cyclization Strategy: Mechanistic and Binding Studies

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