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

Huang, Zhengguo; Dai, Yumei; Yu, Lei

doi:10.1007/s11224-010-9621-y

Cited by 21 publications

(8 citation statements)

References 30 publications

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“…Quantum theory of atoms in molecules (QTAIM) has been proved to be a very useful tool in describing electron densities in H-bonded systems [13,[42][43][44][45][46][47]. Especially, according to QTAIM theory, Koch and Popelier [48] proposed a set of criteria for the existence of H-bond.…”

Section: Qtaim Analysismentioning

confidence: 99%

Hydrogen bonding interactions between N,N-dimethylformamide and cysteine: DFT studies of structures, properties, and topologies

Huang

Dai

et al. 2010

Struct Chem

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The hydrogen bonding interactions between cysteine and N,N-dimethylformamide (DMF) were studied at the extended hybrid functional DFT-X3LYP/6-311??G(d,p) level regarding their geometries, energies, vibrational frequencies, and topological features of the electron density. The quantum theory of atoms in molecules (QTAIM) and natural bond orbital (NBO) analyses were employed to elucidate the interaction characteristics in the complexes. The results show that two intermolecular hydrogen bonds (H-bonds) are formed in one complex except few complexes with one intermolecular H-bond. The H-bonds involving O atom of DMF as H-bond acceptor usually are red-shifting H-bonds, while the blueshifting H-bond usually involve methyl of DMF or methenyl of cysteine moiety as H-bond donors. Both hydrogen bonding interaction and structural deformation play important roles in the relative stabilities of the complexes. Due to the p-bond cooperativity, the strongest H-bond is formed between hydroxyl of cysteine moiety and O atom of DMF, however, the serious deformation counteract the hydrogen bonding interaction to a great extent. The complex involves a stronger hydrogen bonding interaction as well as the smaller deformation is the most stable one. The electron density (q b ) as well as its Laplacian (r 2 q b ) at the H-bond critical point predicted by QTAIM is strongly correlated with the H-bond structural parameter (dR HÁÁÁY ) and the second-perturbation energies E(2) in the NBO scheme.

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Section: Qtaim Analysismentioning

confidence: 99%

Hydrogen bonding interactions between N,N-dimethylformamide and cysteine: DFT studies of structures, properties, and topologies

Huang

Dai

et al. 2010

Struct Chem

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“…Weak interactions, especially hydrogen bonding interaction, play important roles in biological systems [21][22][23][24][25][26] . For example, hydrogen bonding interaction construct the structure of DNA and RNA (bonding between nitrogenous bases), the secondary structure of proteins (helix or pleated sheet) and the different branching patterns of sugar chains.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Hydrogen Bonding Interactions in Paracetamol-Water Complexes

Zhang

Wang

et al. 2018

J. Chil. Chem. Soc.

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The paracetamol-water (PA-H 2 O) complexes formed by hydrogen bonding interactions were investigated at the MP2/6-311++G(d,p) level. Six PA-H 2 O complexes possessing various types of hydrogen bonds (H-bonds) were characterized by geometries, energies, vibrational frequencies. Natural bond orbital (NBO), quantum theory of atoms in molecules (QTAIM) and the localized molecular orbital energy decomposition analysis (LMO-EDA) were performed to explore the nature of the hydrogen-bonding interactions in these complexes. The intramolecular H-bond formed between the methylene and carbonyl oxygen atom of paracetamol is retained in most of complexes. The H-bonds in PW1 and PW6 are stronger than other H-bonds, moreover, the researches show that both the hydrogen bonding interaction and structural deformation play important roles for the relative stabilities of PA-H 2 O complexes.Keyword: paracetamol; hydrogen bonding interactions; natural bond orbital (NBO); quantum theory of atoms in molecules (QTAIM)

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“…From the view of the structural parameters of H‐bond, the SH2 A ···O B H‐bond in AB1 seems to be the strongest red‐shifted H‐bond due to the largest Δ R XH (0.006 Å) and the largest bond angle (166.2°). However, because of different atom as H‐acceptor in different H‐bonds, R H···Y cannot be used directly, so a H‐bond parameter, δ R H···Y 26, is defined as where R

_{vDW}^{H}

and R

_{vDW}^{Y}

are van der Waals radii of H and Y atoms given by Bondi27, respectively, R H···Y is the distance between H‐donor and H‐acceptor. As shown in Table I, the largest value of δ R H···Y is 0.615 Å for the NH3 A ···O B H‐bond in AB5 , which is larger than that of above SH2 A ···O B H‐bond in AB1 .…”

Section: Resultsmentioning

confidence: 99%

Structures, vibrational frequencies, topologies, and energies of hydrogen bonds in cysteine‐formaldehyde complexes

Wang

Huang

et al. 2011

Int J of Quantum Chemistry

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ABSTRACT:The hydrogen bonding interactions between cysteine (Cys) and formaldehyde (FA) were studied with density functional theory regarding their geometries, energies, vibrational frequencies, and topological features of the electron density. The quantum theory of atoms in molecules and natural bond orbital analyses were employed to elucidate the interaction characteristics in the Cys-FA complexes. The intramolecular hydrogen bonds (H-bonds) formed between the hydroxyl and the N atom of cysteine moiety in some Cys-FA complexes were strengthened because of the cooperativity. Most of intermolecular H-bonds involve the O atom of cysteine/FA moiety as proton acceptors, while the strongest H-bond involves the O atom of FA moiety as proton acceptor, which indicates that FA would rather accept proton than providing one. The H-bonds formed between the CH group of FA and the S atom of cysteine in some complexes are so weak that no hydrogen bonding interactions exist among them. In most of complexes, the orbital interaction of H-bond is predominant during the formation of complex. The electron density (q b ) and its Laplace (! 2 q b ) at the bond critical point significantly correlate with the H-bond parameter dR, while a linearly relationship between the second-perturbation energy E(2) and q b has been found as well.

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

Cited by 21 publications

References 30 publications

Hydrogen bonding interactions between N,N-dimethylformamide and cysteine: DFT studies of structures, properties, and topologies

Hydrogen bonding interactions between N,N-dimethylformamide and cysteine: DFT studies of structures, properties, and topologies

Theoretical Study on the Hydrogen Bonding Interactions in Paracetamol-Water Complexes

Structures, vibrational frequencies, topologies, and energies of hydrogen bonds in cysteine‐formaldehyde complexes

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