DFT and AIM studies on two-ring resonance assisted hydrogen bonds

Wojtulewski, Sławomir; Grabowski, Sławomir J.

doi:10.1016/s0166-1280(02)00608-5

Cited by 62 publications

(53 citation statements)

References 27 publications

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“…Interaction energy clearly manifest that the anti-parallel conformation is more stable in C/C180 and the same twisted conformation also have higher aromatic NICS(CCP) value. There are number of illustrations, where the ρ(r c ) at the HBCP has been shown to display the linear relationship with interaction energy of the hydrogen-bonded complexes [38][39][40][41][42][43][44][45][46][47].…”

Section: Resultsmentioning

confidence: 99%

“…Popelier et al have used electron density and other integrated atomic properties of electron density to understand a variety of chemical issues [26,[33][34][35][36][37]. Grabowski et al have made numerous theoretical calculations in relating the various parameters describing the electron density topography and hydrogen bond strength [38][39][40][41][42][43][44][45][46]. Cubero et al have used AIM theory to address hydrogen bonding versus anti-hydrogen bonding and have provided an atomic rationale for the blue shifting [47].…”

Section: Introductionmentioning

confidence: 99%

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Stacking Interactions in Benzene and Cytosine Dimers: From Molecular Electron Density Perspective

Parthasarathi

Subramanian

2005

Struct Chem

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The stacking patterns of benzene and cytosine have been compared with the help of Bader's theory of atoms in molecule using the conventional ab initio method. In addition, the differences in the stacking and hydrogen-bonded interactions in cytosine have also been quantified with the help of various topographical features of molecular electron density. The electron density at the bond critical point does not exhibit linear relationship with the strength of stacking interaction in various twisted cytosine dimers. However, the electron density and Laplacian of electron density at the cage critical point display good linear relationship with the stacking energy. The values of the electron density and Laplacian of electron density derived from AIM theory is highly useful in differentiating stacking and hydrogen-bonded interaction. The aromaticity of cytosine and cytosine stack has been compared with benzene and benzene stack employing NICS criteria.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Stacking Interactions in Benzene and Cytosine Dimers: From Molecular Electron Density Perspective

Parthasarathi

Subramanian

2005

Struct Chem

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“…However, this approach is not useful for the intramolecular hydrogen bonds. Some groups [23,47,[57][58][59][60][61][62] have estimated hydrogen bond energy as the difference between the energy of 'close' and 'open' conformations. Recently, Koll et al [62] corrected the energy of intramolecular hydrogen bond formation in Mannich bases, for the non-bonded interactions within the molecules.…”

Section: Hydrogen Bonding Energymentioning

confidence: 99%

“…This type of hydrogen bond is called the resonanceassisted hydrogen bond (RAHB) and has been a subject of extensive experimental and computational studies [19][20][21][22][23][24][25][26][27][28][29][30][31]. Gilli et al [19][20][21][22][23][24][25][26][27][28][29][30][31] defined RAHB as the hydrogen bond where donor and acceptor are connected by a p-conjugated system, which establishes an interplay between p-delocalization effect and strengthening of the hydrogen-bond.…”

Section: Introductionmentioning

confidence: 99%

“…Gilli et al [19][20][21][22][23][24][25][26][27][28][29][30][31] defined RAHB as the hydrogen bond where donor and acceptor are connected by a p-conjugated system, which establishes an interplay between p-delocalization effect and strengthening of the hydrogen-bond. RAHBs were sub-classified further to homonuclear and heteronuclear type of H-bonds.…”

Section: Introductionmentioning

confidence: 99%

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DFT studies and AIM analysis of intramolecular N–H···O hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2,3-dihydro-2λ5-[1,2]oxaphosphinin-4-one and its derivatives

Małecka

2009

Struct Chem

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The intramolecular N-HÁÁÁO hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2, 3-dihydro-2k 5 -[1,2]oxaphosphinin-4-one and its derivatives (F, H, Li, -BeH) were studied by DFT (density functional theory) methods. The results of calculations were obtained at B3LYP/6-311??G(d,p) level on model species, with the resonance-assisted hydrogen bonds (RAHB). Topological parameters such an electron density, its Laplacian, kinetic electron energy density, potential electron energy density, and total electron energy density at the bond critical points (BCP) of HÁÁÁO/N-H contact bonds from Bader's 'Atoms in molecules' (AIM) theory were analyzed in details. The energy of the N-HÁÁÁO interactions studied here was found rather weak (E HB = 2.53-12.08 kcal/mol). The results of AIM ellipticity indicated p-delocalization over all six atoms within ring.

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Chemical Bonding in Polarised Push–Pull Ethylenes

et al. 2019

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1,1‐Diamino‐2,2‐bis(triflyl)ethylenes with both twisted and planar structures around the partial “C=C” bond were synthesised. Bonding properties in these compounds were analysed by an experimental approach using high‐resolution X‐ray diffraction data treated with X‐ray wavefunction refinement (XWR). In the twisted compound, a dominant contribution of the charge‐separated resonance structure was revealed. On the contrary, the nearly planar compound still showed π‐bonding character, however, with a considerable contribution of the charge‐separated resonance structure.

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DFT and AIM studies on two-ring resonance assisted hydrogen bonds

Cited by 62 publications

References 27 publications

Stacking Interactions in Benzene and Cytosine Dimers: From Molecular Electron Density Perspective

Stacking Interactions in Benzene and Cytosine Dimers: From Molecular Electron Density Perspective

DFT studies and AIM analysis of intramolecular N–H···O hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2,3-dihydro-2λ5-[1,2]oxaphosphinin-4-one and its derivatives

Chemical Bonding in Polarised Push–Pull Ethylenes

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