A quantum chemical study of conformational and tautomeric preferences, intramolecular hydrogen bonding and π-electron delocalization on dinitrosomethane; in gas phase and water solution

Jahani, Peyman Mohammadzadeh; Nowroozi, Alireza; Hajiabadi, H.; Hassani, Majid

doi:10.1007/s11224-012-9997-y

Cited by 6 publications

(1 citation statement)

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“…Different empirical approaches have been used to estimate the energies of individual hydrogen bonds in molecular crystals using electron density, geometrical and spectral parameters. For example, an empirical correlation between E int (in kJ/mol) and the O···O distance (Å) has been suggested for intramolecular hydrogen bonds: italicE int = prefix− 23.255 × 10 5 .25em exp ( − 4.12 R false( normalO · · · normalO false) ) This equation provides a successful estimation of the energy of intramolecular hydrogen bonds in the solid state. , …”

Section: Theoreticalmentioning

confidence: 99%

Noncovalent Interactions in Crystalline Picolinic Acid N-Oxide: Insights from Experimental and Theoretical Charge Density Analysis

Shishkina

Zhurov

Сташ

et al. 2013

Crystal Growth & Design

104

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This study provides a detailed description of noncovalent interactions of different types and strengths in the title crystal using a combined experimental and theoretical study of the charge density distribution. The nature of the noncovalent interactions is visualized using information theory and through the superposition of the gradient fields in the electron density and electrostatic potential. The energy of the intramolecular O–H···O bond, intermolecular C–H···O bonds, and π-stacking interactions, E int, are evaluated from empirical correlations between E int and geometrical and electron-density bond critical point parameters. The complete set of noncovalent interactions including the strong intramolecular O–H···O (E int > 90 kJ/mol) and weak C–H···O (E int < 10 kJ/mol) hydrogen bonds, and π-stacking interactions (E int < 4 kJ/mol) is quantitatively described. The results from the experimental charge density analysis are compared with periodic quantum calculations using density functional theory with the Grimme dispersion correction. It was found that the Grimme dispersion correction did not provide a good simultaneous description of both weak and strong noncovalent interactions in the studied crystal. It is shown that the obtained energies of noncovalent interactions lead to a reasonable value of the lattice energy. The latter is treated as the total intermolecular interaction energy.

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