Water Triggers Hydrogen‐Bond‐Network Reshaping in the Glycoaldehyde Dimer

Pérez, Cristóbal; Steber, Amanda L.; Temelso, Berhane; Kisiel, Zbigniew; Schnell, Melanie

doi:10.1002/anie.201914888

Cited by 10 publications

(13 citation statements)

References 32 publications

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“…A similar arrangement was also observed for acenaphthene‐(H 2 O) 3 [22] and CH 2 F 2 ‐(H 2 O) 3 [23] . Interestingly, when complexing with β‐propiolactone, [24] camphor, [25] the glycoaldehyde dimer, [26] or verbenone, [27] the water trimer adopts a chain structure. In the formamide‐(H 2 O) 3 complex, all molecules, including formamide, are located almost in one plane closing a sequential cycle.…”

Section: Introductionsupporting

confidence: 67%

“…Asimilar arrangement was also observed for acenaphthene-(H 2 O) 3 [22] and CH 2 F 2 -(H 2 O) 3 . [23] Interestingly,w hen complexing with b-propiolactone, [24] camphor, [25] the glycoaldehyde dimer, [26] or verbenone, [27] the water trimer adopts ac hain structure.I nt he formamide-(H 2 O) 3 complex, all molecules,i ncluding formamide,a re located almost in one plane closing as equential cycle.Itwas shown that formamide can act as asubstitute of two water molecules,a nd the formamide-(H 2 O) 3 complex mimics the overall structure of the cyclic water pentamer. [28] Thewater trimer thus forms different configurations depending on the solute molecule that it interacts with, highlighting the crucial role of the interplay between the water-water and water-solute interactions.Acomparison of these studies indicates that the water trimer prefers to form chains when it interacts with the solute molecule as aH Bd onor through as trong HB such as OH•••O,o therwise it prefers the cyclic form.…”

Section: Introductionmentioning

confidence: 99%

“…[28] Thewater trimer thus forms different configurations depending on the solute molecule that it interacts with, highlighting the crucial role of the interplay between the water-water and water-solute interactions.Acomparison of these studies indicates that the water trimer prefers to form chains when it interacts with the solute molecule as aH Bd onor through as trong HB such as OH•••O,o therwise it prefers the cyclic form. [18,[21][22][23][24][25][26][27][28] This naturally leads to the question:W hich structure will the water trimer adopt when the solute molecule offers several different docking sites simultaneously?…”

Section: Introductionmentioning

confidence: 99%

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Unlocking the Water Trimer Loop: Isotopic Study of Benzophenone‐(H₂O)_1–3Clusters with Rotational Spectroscopy

Quesada‐Moreno

Pinacho

et al. 2021

Angewandte Chemie

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Examined here are the structures of complexes of benzophenone microsolvated with up to three water molecules by using broadband rotational spectroscopya nd the cold conditions of amolecular jet. The analysis shows that the water molecules dock sideways on benzophenone for the water monomer and dimer moieties,and they move aboveone of the aromatic rings when the water cluster grows to the trimer.The rotational spectra shows that the water trimer moiety in the complex adopts an open-loop arrangement. Ab initio calculations face ad ilemma of identifying the global minimum between the open loop and the closed loop,which is only solved when zero-point vibrational energy correction is applied. An OH•••p bond and aB ürgi-Dunitz interaction between benzophenone and the water trimer are present in the cluster.T his work shows the subtle balance between water-water and water-solute interactions when the solute molecule offers several different anchor sites for water molecules.

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Section: Introductionsupporting

confidence: 67%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Unlocking the Water Trimer Loop: Isotopic Study of Benzophenone‐(H₂O)_1–3Clusters with Rotational Spectroscopy

Quesada‐Moreno

Pinacho

et al. 2021

Angewandte Chemie

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“…Hydrogen bonds are an important type of interaction that stabilizes the crystal packing of small molecules, structures of proteins, and various geometries of coordination compounds. − One of the most studied hydrogen bonds is between water molecules. − It was shown that the most stable geometry of water dimers has an interaction energy of ca. −4.84 kcal/mol .…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere

Živković¹,

Milovanović²,

Zarić

2022

Crystal Growth & Design

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In the study of hydrogen bonds between noncoordinated and metal-coordinated ethylenediamine and a water molecule, the data in the Cambridge Structural Database (CSD) were analyzed and DFT calculations were performed. For coordinated ethylenediamine in the CSD, the analyzed distributions of d OH distances show a maximum in the range of 2.0–2.1 Å, while the angle α shows a maximum in the range of 150–160°. The DFT calculations were done for octahedral geometries of cobalt(III), copper(II), and nickel(II) complexes and square-planar geometry of palladium(II) complexes. The coordination of ethylenediamine to the metal ions strengthens its hydrogen bond with the water molecule. Namely, noncoordinated ethylenediamine and the water molecule have an interaction energy of −2.3 kcal/mol, while for coordinated ethylenediamine, the interacting energy spans from −4.0 to −28.0 kcal/mol depending on the metal ion and charge of the complex. The hydrogen bond energies have a good correlation with the calculated electrostatic potential on the interacting hydrogen atom. The coordination number and oxidation states of the metal have a significant influence on the electrostatic potential on the interacting hydrogen atom and the energy of hydrogen bonds.

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“…Although hydrogen bonds involving water molecules and other conventional hydrogen donors and acceptors are extensively studied, − numerous cases in which hydrogen donors are coordinated to transition metal atoms are yet to be systematically examined. In this work, we studied energies and geometries of hydrogen bonds between noncoordinated and coordinated ammonia and water using a combination of statistical analysis of crystallographic data from the Cambridge Structural Database (CSD) and accurate quantum chemical calculations.…”

Section: Introductionmentioning

confidence: 99%

Strong Hydrogen Bonds of Coordinated Ammonia Molecules

Živković¹,

Veljković

Zarić

2021

Crystal Growth & Design

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The hydrogen bonds of noncoordinated (NH/O) and coordinated ammonia (MLNH/O) with water molecules were studied by analyzing data in the Cambridge Structural Database (CSD) and by DFT calculations. The data from the CSD on the distribution of hydrogen bond d HO distances of the coordinated ammonia show a peak in the range of 2.0−2.2 Å with a significant number of hydrogen bonds in the range of 1.8−2.0 Å. Analysis of Hirshfeld surfaces showed that coordinated NH 3 molecules are involved in numerous noncovalent contacts. The DFT calculations were performed on linear complexes of silver(I), square-planar complexes of platinum(II), tetrahedral complexes of zinc(II), and octahedral complexes of cobalt(III) by varying the charge of the complexes. The calculated data show that coordinated ammonia has stronger hydrogen bonds than noncoordinated ammonia, even for neutral complexes. The hydrogen bond energy of noncoordinated ammonia is −2.3 kcal/mol, while for coordinated ammonia, attractive interactions are in the range of −3.7 to −25.0 kcal/mol, depending on the metal ion and charge of the complex. The interaction energies for metal complexes from neutral to charged species are for the linear silver(I) complex from −6.0 to −10.7 kcal/mol, while for the square planar complex, interactions span from −5.9 to −19.9 kcal/mol. The tetrahedral zinc(II) complexes have interaction energy from −5.5 to −17.5 kcal/mol, while for the octahedral cobalt(III) complex, attractive interaction energies are from −3.7 to −25.0 kcal/mol. With the increasing charge of the metal complex, the hydrogen bond between coordinated ammonia and free water becomes stronger, and in accordance with that, the d HO distance becomes shorter. The bifurcated interaction is stronger than monofurcated for all complexes. The interaction energies correspond well with the electrostatic potential (Vs) values on interacting hydrogen atoms; the more positive Vs values on hydrogen atoms lead to stronger interaction. The hydrogen bond between ammonia and water molecules (−2.3 kcal/mol) is quite weak in comparison to the water/water hydrogen bond; it is 50% of the water/water hydrogen bond (−4.84 kcal/mol). Although the hydrogen bonds of coordinated ammonia are also weaker than hydrogen bonds of coordinated water molecules, the difference is smaller, indicating the importance of the coordination on the strength of hydrogen bonds.

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Water Triggers Hydrogen‐Bond‐Network Reshaping in the Glycoaldehyde Dimer

Cited by 10 publications

References 32 publications

Unlocking the Water Trimer Loop: Isotopic Study of Benzophenone‐(H₂O)_1–3Clusters with Rotational Spectroscopy

Unlocking the Water Trimer Loop: Isotopic Study of Benzophenone‐(H₂O)_1–3Clusters with Rotational Spectroscopy

Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere

Strong Hydrogen Bonds of Coordinated Ammonia Molecules

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Water Triggers Hydrogen‐Bond‐Network Reshaping in the Glycoaldehyde Dimer

Cited by 10 publications

References 32 publications

Unlocking the Water Trimer Loop: Isotopic Study of Benzophenone‐(H2O)1–3Clusters with Rotational Spectroscopy

Unlocking the Water Trimer Loop: Isotopic Study of Benzophenone‐(H2O)1–3Clusters with Rotational Spectroscopy

Hydrogen Bonds of Coordinated Ethylenediamine and a Water Molecule: Joint Crystallographic and Computational Study of Second Coordination Sphere

Strong Hydrogen Bonds of Coordinated Ammonia Molecules

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Unlocking the Water Trimer Loop: Isotopic Study of Benzophenone‐(H₂O)_1–3Clusters with Rotational Spectroscopy

Unlocking the Water Trimer Loop: Isotopic Study of Benzophenone‐(H₂O)_1–3Clusters with Rotational Spectroscopy