Nalazite se na CroRIS probnoj okolini. Ovdje evidentirani podaci neće biti pohranjeni u Informacijskom sustavu znanosti RH. Ako je ovo greška, CroRIS produkcijskoj okolini moguće je pristupi putem poveznice www.croris.hr
izvor podataka: crosbi

Contribution of Different Crystal Packing Forces in π‑Stacking: From Noncovalent to Covalent Multicentric Bonding (CROSBI ID 269329)

Prilog u časopisu | pregledni rad (znanstveni) | međunarodna recenzija

Molčanov, Krešimir ; Milašinović, Valentina ; Kojić-Prodić, Biserka Contribution of Different Crystal Packing Forces in π‑Stacking: From Noncovalent to Covalent Multicentric Bonding // Crystal growth & design, 19 (2019), 5976-5980. doi: 10.1021/acs.cgd.9b00540

Podaci o odgovornosti

Molčanov, Krešimir ; Milašinović, Valentina ; Kojić-Prodić, Biserka

engleski

Contribution of Different Crystal Packing Forces in π‑Stacking: From Noncovalent to Covalent Multicentric Bonding

The present review is aimed to compare crystal packing interactions contributing to stacking arrangements of primarily nonaromatic systems referring only briefly to classical aromatic stacking. The classical aromatic stacking is mainly based on weak dispersion interactions (E ≤ 1 kcal mol–1) whereas heteroaromatics reveal more electrostatic (or specifically dipolar) contributions (E = 5–10 kcal mol–1). Based mainly on our charge density studies and DFT calculations, the results show that (i) all planar rings stack, regardless of aromaticity (or delocalization of π electrons) and (ii) stacking interactions cover a wide continuum ranging from weak, mainly dispersion interactions (E < 5 kcal mol–1) to unlocalized two-electron multicentric (2e/mc) covalent bonds (“pancake bonds”, E > 15 kcal mol–1). Our recent studies showed that quinones form face-to-face stacks and the energies of interactions exceed 10 kcal mol–1 ; ours and other authors’ results indicate that interactions between planar radicals involve a significant contribution of covalent bonding. Thus, π-interactions cover a broad range of energies, ranging from ≤1 to ≥20 kcal mol–1, and the interactions span from weak dispersion to multicentric covalent bonding. Therefore, development of a universal model of stacking is needed. In this respect, stacking can be compared to hydrogen bonding, which also ranges between dispersion (weakest hydrogen bonds, such as C–H···S and C–H···Cl) and two-electron/three-centric covalent bonding (the strongest “symmetrical” hydrogen bonds).

π-interactions ; aromatic ; non-aromatic ; multicentric covalent bonding-'pancake' bonding ; crystal engineering

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

Podaci o izdanju

19

2019.

5976-5980

objavljeno

1528-7483

1528-7505

10.1021/acs.cgd.9b00540

Povezanost rada

Kemija

Poveznice
Indeksiranost