A bond-length-bond-order relationship for intermolecular interactions based on the topological properties of molecular charge distributions

Boyd, Russell J.; Choi, S. C.

doi:10.1016/0009-2614(85)87017-2

Cited by 123 publications

(61 citation statements)

References 21 publications

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“…In the analysis of qðrÞ, characterization of bonding interactions is often performed in terms of local properties at this critical point. In the case of the hydrogen bond (HB), empirical dependencies between some of these properties at BCP and the energy ðE HB Þ of this intermolecular interaction have been reported [2][3][4]. While these dependencies were initially observed from theoretical calculations on simple dimers in gas phase, similar ones derived from experimental charge density studies established that bonding distance and properties at BCP can be used for the estimation of the HB energy in solid state [5].…”

Section: Introductionmentioning

confidence: 94%

Relationships between interaction energy, intermolecular distance and electron density properties in hydrogen bonded complexes under external electric fields

Mata

Alkorta

Espinosa

et al. 2011

Chemical Physics Letters

327

186

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Section: Introductionmentioning

confidence: 94%

Relationships between interaction energy, intermolecular distance and electron density properties in hydrogen bonded complexes under external electric fields

Mata

Alkorta

Espinosa

et al. 2011

Chemical Physics Letters

327

186

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“…[11] This method was applied for the first time to a large set of 83 experimentally determined XÀH···O (X = O, N, C) hydrogen bonds [12] and its validity tested against a set of 32 theoretically calculated XÀH···FÀY interactions. [13] Dependencies between topological properties and bonding distances were first observed for HBs, [14] and after for other interactions, [15] by means of theoretical calculations on molecules and complexes in gas phase. Since then, many dependencies involving 1(r) properties at the BCP have been reported and used in theoretical analyses of complexes in the gas phase, such as those given in the detailed study of NÀH···N interactions.…”

Section: Introductionmentioning

confidence: 98%

Universal Features of the Electron Density Distribution in Hydrogen‐Bonding Regions: A Comprehensive Study Involving H⋅⋅⋅X (X=H, C, N, O, F, S, Cl, π) Interactions

Mata

Alkorta

Molins

et al. 2010

Chemistry A European J

236

124

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Topological analyses of the theoretically calculated electron densities for a large set of 163 hydrogen-bonded complexes show that HX interactions can be classified in families according to X (X=atom or pi orbital). Each family is characterised by a set of intrinsic dependencies between the topological and energetic properties of the electron density at the hydrogen-bond critical point, as well as between each of them and the bonding distance. Comparing different atom-acceptor families, these dependencies are classified as a function of the van der Waals radius r(X) or the electronegativity chi(X), which can be explained in terms of the molecular orbitals involved in the interaction. According to this ordering, the increase of chi(X) leads to a larger range of HX distances for which the interaction is of pure closed-shell type. Same dependencies observed for HO interactions experimentally characterised by means of high-resolution X-ray diffraction data show a good agreement with those obtained from theoretical calculations, in spite of a larger dispersion of values around the expected fitting functions in the experimental case. Theoretical dependencies can thus be applied to the analysis of the experimental electron density for detecting either unconventional hydrogen bonds or problems in the modelling of the experimental electron density.

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“…This last point is of special importance as a reminder that hydrogen bonds are mainly due to electrostatic interactions. Figures 3 and 4, respectively, present the isodensity con- As noted by Boyd and Choi (19), the charge density at the bond critical point of the hydrogen bond is paralleled by the increase in the hydrogen bond strength. In this sense, the ').…”

Section: Resultsmentioning

confidence: 70%

Intramolecular hydrogen bonding in ribonucleoside sugar hydroxyls. An abinitio study

Bosch¹,

Moreno²,

Lluch³

1992

Can. J. Chem.

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. 70, 1640 (1 992).Ab initio self-consistent field (SCF) calculations were done for a model of a ribonucleoside where only the ring part of the furanoside form of D-ribose is considered. Full geometry optimization and direct location of stationary points were used in order to characterize the geometry of the minimum energy structure and of the transition state for the proton transfer reaction in the anion. Topological analysis of the charge density and its Laplacian for the minimum energy structure allow us to find clear electronic and geometrical evidence of an intramolecular hydrogen bond. On the other hand, our results show a very low energy barrier for the proton transfer so that the proton jumps easily between the two oxygen atoms.ENRIC BOSCH, MIQUEL MORENO et JOSE M. LLUCH. Can. J. Chem. 70, 1640Chem. 70, (1992.On a effectuC des calculs ab initio en champ auto-cohCrent (SCF) sur un modkle de ribonuclCoside dans lequel on ne considkre que la partie cyclique de la forme furanoside du D-ribose. On a utilisC une optimisation compltte de la gComCtrie et une location directe des points stationnaires pour caractkriser la gComCtrie de la structure posskdant une tnergie minimale et de 1'Ctat de transition de la rCaction du transfert de proton dans l'anion. Une analyse topologique de la densit6 de charge et de son laplacien pour la structure d'Cnergie minimale nous permet d'obtenir des donnCes Clectronique et gComCtrique non-ambigues concernant une liaison hydrogkne intramolCculaire. Par ailleurs, nos rCsultats montrent que la barritre d'energie pour le transfert du proton est faible; il en rksulte que le proton passe facilement d'un oxygtne 2 l'autre.[Traduit par la rCdaction]

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A bond-length-bond-order relationship for intermolecular interactions based on the topological properties of molecular charge distributions

Cited by 123 publications

References 21 publications

Relationships between interaction energy, intermolecular distance and electron density properties in hydrogen bonded complexes under external electric fields

Relationships between interaction energy, intermolecular distance and electron density properties in hydrogen bonded complexes under external electric fields

Universal Features of the Electron Density Distribution in Hydrogen‐Bonding Regions: A Comprehensive Study Involving H⋅⋅⋅X (X=H, C, N, O, F, S, Cl, π) Interactions

Intramolecular hydrogen bonding in ribonucleoside sugar hydroxyls. An abinitio study

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