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A polar/π model of interactions explains face-to-face stacked quinoid rings: a case study of the crystal of potassium hydrogen chloranilate dihydrate (CROSBI ID 221779)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Molčanov, Krešimir ; Stare, Jernej ; Kojić-Prodić, Biserka ; Lecomte, Claude ; Dahaoui, Slimane ; Jelsch, Christian ; Wenger, Emmanuel ; Šantić, Ana ; Zarychta, Bartosz A polar/π model of interactions explains face-to-face stacked quinoid rings: a case study of the crystal of potassium hydrogen chloranilate dihydrate // Crystengcomm, 17 (2015), 8645-8656. doi: 10.1039/c5ce01037c

Podaci o odgovornosti

Molčanov, Krešimir ; Stare, Jernej ; Kojić-Prodić, Biserka ; Lecomte, Claude ; Dahaoui, Slimane ; Jelsch, Christian ; Wenger, Emmanuel ; Šantić, Ana ; Zarychta, Bartosz

engleski

A polar/π model of interactions explains face-to-face stacked quinoid rings: a case study of the crystal of potassium hydrogen chloranilate dihydrate

The nature of interactions between face-to-face staggered stacked quinoid rings with π-systems, observed with short inter-ring centroid∙∙∙centroid distance is analyzed by experimental and theoretical methods. Charge density studies based on X-ray diffraction and DFT calculations, complemented by impedance spectroscopy were employed to define the electronic and structural characteristics of the quinoid rings responsible for their interactions within the crystal packing. The crystal packing is mainly stabilized by strong electrostatic interactions between K+ cation and the hydrogen chloranilate anion. The proximity and orientation of the stacked quinoid rings in parallel glide-plane arrangement is partly governed by the non-covalent interactions within the dimer. The estimated contribution of dispersion energy to the stacking of the rings about -10 kcal mol-1, as calculated by DFT methods, is comparable to medium-strong hydrogen bonding. The electronic structure of 2, 5-dihydroxyquinonate monoanion exhibits alternating electron-rich and electron-poor regions. The calculated electrostatic energy shows variations with the relative orientation of rings within dimers reaching ca. 10-15 kcal mol-1. Thus, the nature of interactions between π-systems of quinoid rings can be described by a polar/π model where electrostatic complementarity plays a determinant role in π-stacking orientation. These interactions have a great potential in crystal engineering and may be employed in design of functional materials.

pi-interactions ; chloranilic acid ; X-ray charge density ; periodic DFT ; intermolecular interaction

Djelomično financirala Zaklada HAZU (za 2014. godinu) i hrvatsko-francuska bilaterala - Cogito.

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Podaci o izdanju

17

2015.

8645-8656

objavljeno

1466-8033

10.1039/c5ce01037c

Povezanost rada

Kemija

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