Hydrogen bonds and ionic interactions in Guanidine/Guanidinium complexes: a computational case study

Rozas, Isabel; Alkorta, Ibón; Elguero, José

doi:10.1007/s11224-008-9377-9

Cited by 30 publications

(29 citation statements)

References 56 publications

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“…DFT has been accepted by the ab initio quantum chemistry community as a cost-effective approach for the computation of molecular structures, vibrational frequencies, and energies of chemical reactions. Recently, DFT has been used widely to study H-bond interactions [13][14][15][16]. Generally, the formation of H-bond can be estimated by the structural parameters (e.g.…”

Section: Introductionmentioning

confidence: 99%

Combined DFT with NBO and QTAIM studies on the hydrogen bonds in (CH3OH) n (n = 2–8) clusters

Huang

Dai

2010

Struct Chem

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The (CH 3 OH) n (n = 2-8) clusters formed via hydrogen bond (H-bonds) interactions have been studied systemically by density functional theory (DFT). The relevant geometries, energies, and IR characteristics of the intermolecular OHÁÁÁO H-bonds have been investigated. The quantum theory of atoms in molecule (QTAIM) and natural bond orbital (NBO) analysis have also been applied to understand the nature of the hydrogen bonding interactions in clusters. The results show that both the strength of H-bonds and the deformation are important factors for the stability of (CH 3 OH) n clusters. The weakest H-bond was found in the dimer. The strengths of H-bonds in clusters increase from n = 2 to 8, moreover, the strengths of H-bonds in (CH 3 OH) n (n = 4-8) clusters are remarkably stronger than those in (CH 3 OH) n (n = 2, 3) clusters. The small differences of the strengths of H-bonds among (CH 3 OH) n (n = 6-8) clusters indicate that a partial covalent character is attributed to the H-bonds in these clusters. The linear relationships between the electron density of BCP (q b ) and the HÁÁÁO bond length of H-bonds as well as the second-perturbation energies E(2) have also been investigated and used to study the nature of H-bonds, respectively.Keywords The quantum theory of atoms in molecule (QTAIM) Á Natural bond orbital (NBO) Á Density functional theory (DFT) Á Hydrogen bond Á Methanol clusters

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Section: Introductionmentioning

confidence: 99%

Combined DFT with NBO and QTAIM studies on the hydrogen bonds in (CH3OH) n (n = 2–8) clusters

Huang

Dai

2010

Struct Chem

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“…?G(d,p) basis set [16,17] was used. B3LYP has been accepted as a cost-effective and reliable approach for predicting H-bonds of biological molecules [18][19][20][21][22]. First, the structures of AdH ?…”

Section: Computational Detailsmentioning

confidence: 99%

Density functional theory and topological analysis on the hydrogen bonding interactions in N-protonated adrenaline–DMSO complexes

Huang

Dai

2010

Struct Chem

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In this study, complexes formed via hydrogen bond interactions between N-protonated adrenaline (AdH ? ) and DMSO have been studied by density functional theory (DFT). The relevant geometries, energies, and IR characteristics of the hydrogen bonds (H-bonds) have been systematically investigated. The natural bond orbital (NBO) and the quantum theory of atoms in molecule (QTAIM) analysis have also been applied to understand the nature of the hydrogen bonding interactions in complexes. The H-bonds involving amino or hydroxyls as H-donor are dominant H-bonds in complexes and are attributed to strong H-bonds. The weak H-bonds, such as p H-bonds and H-bonds involving methyl (DMSO) or methenyls (C2H6 and C5H7 of AdH ? ) as H-acceptors, were found in complexes as well. The complexes in which the dominant H-bond involves amino of AdH ? as H-donor are more stable than those with the dominant H-bond involving hydroxyls as H-donor. Some relationships between various properties of QTAIM, NBO, geometry as well as frequency were also investigated.

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“…Hydrogen bonds are the most common interaction that occurs within and between different macromolecules and between macromolecules and small ligands in biological systems; at biological pH, many of these species are charged, which increases the strength of the hydrogen bonds [299]. The next article presented a study by Rozas et al [299] that was conducted with the objective of using computational methods to analyze the different interactions that can occur in the guanidine (neutral)/guanidinium (cation) and chloride (anion)/hydrochloric acid (neutral) systems.…”

Section: Issuementioning

confidence: 99%

“…The next article presented a study by Rozas et al [299] that was conducted with the objective of using computational methods to analyze the different interactions that can occur in the guanidine (neutral)/guanidinium (cation) and chloride (anion)/hydrochloric acid (neutral) systems. The authors analyzed all of the possible one-toone interactions between these molecules/ions (neutralneutral, neutral-anion, cation-neutral, and cation-anion) to determine the influence of the ionic interactions on the hydrogen bond interactions.…”

Section: Issuementioning

confidence: 99%

Interplay of thermochemistry and Structural Chemistry, the journal (volume 19, 2008) and the discipline

et al. 2009

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Hydrogen bonds and ionic interactions in Guanidine/Guanidinium complexes: a computational case study

Cited by 30 publications

References 56 publications

Combined DFT with NBO and QTAIM studies on the hydrogen bonds in (CH3OH) n (n = 2–8) clusters

Combined DFT with NBO and QTAIM studies on the hydrogen bonds in (CH3OH) n (n = 2–8) clusters

Density functional theory and topological analysis on the hydrogen bonding interactions in N-protonated adrenaline–DMSO complexes

Interplay of thermochemistry and Structural Chemistry, the journal (volume 19, 2008) and the discipline

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