On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms
This manuscript reports the synthesis and X-ray characterization of two octahydro-1H-4,6-epoxycyclopenta[<i>c</i>]pyridin-1-one derivatives that contain the four most abundant halogen atoms (Ha) in the structure with the aim of studying the formation of Ha···Ha halogen bonding interactio...
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MDPI AG
2021
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oai:doaj.org-article:e4c9e4c8d2234528af7be5e39d60b7bd2021-11-25T17:19:28ZOn the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms10.3390/cryst111114062073-4352https://doaj.org/article/e4c9e4c8d2234528af7be5e39d60b7bd2021-11-01T00:00:00Zhttps://www.mdpi.com/2073-4352/11/11/1406https://doaj.org/toc/2073-4352This manuscript reports the synthesis and X-ray characterization of two octahydro-1H-4,6-epoxycyclopenta[<i>c</i>]pyridin-1-one derivatives that contain the four most abundant halogen atoms (Ha) in the structure with the aim of studying the formation of Ha···Ha halogen bonding interactions. The anisotropy of electron density at the heavier halogen atoms provokes the formation of multiple Ha···Ha contacts in the solid state. That is, the heavier Ha-atoms exhibit a region of positive electrostatic potential (σ-hole) along the C–Ha bond and a belt of negative electrostatic potential (σ-lumps) around the atoms. The halogen bonding assemblies in both compounds were analyzed using density functional theory (DFT) calculations, molecular electrostatic potential (MEP) surfaces, the quantum theory of “atom-in-molecules” (QTAIM), the noncovalent interaction plot (NCIplot), and the electron localization function (ELF).Dmitriy F. MertsalovRosa M. GomilaVladimir P. ZaytsevMikhail S. GrigorievEugeniya V. NikitinaFedor I. ZubkovAntonio FronteraMDPI AGarticlehalogen bondingcrystal engineeringsupramolecular chemistryσ-holeCrystallographyQD901-999ENCrystals, Vol 11, Iss 1406, p 1406 (2021) |
| institution |
DOAJ |
| collection |
DOAJ |
| language |
EN |
| topic |
halogen bonding crystal engineering supramolecular chemistry σ-hole Crystallography QD901-999 |
| spellingShingle |
halogen bonding crystal engineering supramolecular chemistry σ-hole Crystallography QD901-999 Dmitriy F. Mertsalov Rosa M. Gomila Vladimir P. Zaytsev Mikhail S. Grigoriev Eugeniya V. Nikitina Fedor I. Zubkov Antonio Frontera On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms |
| description |
This manuscript reports the synthesis and X-ray characterization of two octahydro-1H-4,6-epoxycyclopenta[<i>c</i>]pyridin-1-one derivatives that contain the four most abundant halogen atoms (Ha) in the structure with the aim of studying the formation of Ha···Ha halogen bonding interactions. The anisotropy of electron density at the heavier halogen atoms provokes the formation of multiple Ha···Ha contacts in the solid state. That is, the heavier Ha-atoms exhibit a region of positive electrostatic potential (σ-hole) along the C–Ha bond and a belt of negative electrostatic potential (σ-lumps) around the atoms. The halogen bonding assemblies in both compounds were analyzed using density functional theory (DFT) calculations, molecular electrostatic potential (MEP) surfaces, the quantum theory of “atom-in-molecules” (QTAIM), the noncovalent interaction plot (NCIplot), and the electron localization function (ELF). |
| format |
article |
| author |
Dmitriy F. Mertsalov Rosa M. Gomila Vladimir P. Zaytsev Mikhail S. Grigoriev Eugeniya V. Nikitina Fedor I. Zubkov Antonio Frontera |
| author_facet |
Dmitriy F. Mertsalov Rosa M. Gomila Vladimir P. Zaytsev Mikhail S. Grigoriev Eugeniya V. Nikitina Fedor I. Zubkov Antonio Frontera |
| author_sort |
Dmitriy F. Mertsalov |
| title |
On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms |
| title_short |
On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms |
| title_full |
On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms |
| title_fullStr |
On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms |
| title_full_unstemmed |
On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms |
| title_sort |
on the importance of halogen bonding interactions in two x-ray structures containing all four (f, cl, br, i) halogen atoms |
| publisher |
MDPI AG |
| publishDate |
2021 |
| url |
https://doaj.org/article/e4c9e4c8d2234528af7be5e39d60b7bd |
| work_keys_str_mv |
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| _version_ |
1718412501867036672 |