Characteristics of planar and planar layer-stacked CHON-containing molecules

Guo, Shitai; Xue, Kairui; Huang, Jing; Zhu, Weihua; Zhang, Chaoyang

doi:10.1039/d3ce01177a

Cited by 2 publications

(13 citation statements)

References 60 publications

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“…Very recently, we focused upon it based on the existing experimentally observed crystal packing and filled in the blank. 41,42 We constructed a data set comprising 65 planar layer-stacked molecules and confirmed that six point groups are covered therein with C s weighting the most heavily, high planarity tends to result in planar layer-stacking, and intermolecular HBs and the C�O group appear frequently to maintain the layers. 41 Still, the crystal packing of the remaining 55 molecules with lower symmetry remains unclear.…”

Section: Introductionmentioning

confidence: 73%

“…Notably, molecules containing exclusively O−H bonds appear rarely, with only one sample of KECYBU02. 41 3.1. Stacking of H-free Molecules.…”

Section: Resultsmentioning

confidence: 99%

“…In fact, there is no such relationship that is highly desired. Very recently, we focused upon it based on the existing experimentally observed crystal packing and filled in the blank. , We constructed a data set comprising 65 planar layer-stacked molecules and confirmed that six point groups are covered therein with C s weighting the most heavily, high planarity tends to result in planar layer-stacking, and intermolecular HBs and the CO group appear frequently to maintain the layers . It richens the insight about the planar layer-stacking, in addition to an earlier work by Bu et al, in which 10 molecules with high symmetry of D 2 h or D 3 h were studied, and a strategy for constructing the planar layer-stacked molecules was proposed, discerned by hydrogenous and H-free molecules …”

Section: Introductionmentioning

confidence: 81%

“…42 In fact, we recently confirmed that the planar layer-stacked molecules are not limited in high symmetry, and all the 59 hydrogenous molecules form C/N/ O−H•••N/O HBs, regardless of the molecular symmetry. 41 Weak HBs with length of 2.501 to 2.941 Å are exclusively exhibited in DCHXAL, IHOQIH, MIJJAR, and VENDOH, as depicted in Figure S2 of the Supporting Information. Thus, it is a compliment to the previous insight.…”

Section: Stacking Of Hydrogenous Moleculesmentioning

confidence: 99%

“…The object data includes 65 planar layer-stacked CHON-containing molecules, as collected in our recent work 41 and shown in Figure 1. It exhibits five types of elemental combinations for these molecules, including CN, CHN, CHO, CNO, and CHON.…”

Section: Data Collection and Objectsmentioning

confidence: 99%

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Planar Layer-Stacking of CHON-Containing Molecules

Guo,

Xue,

Zuo

et al. 2024

Crystal Growth & Design

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Understanding the relationship between the molecular structure and crystal packing is fundamental while challenging crystal engineering. Planar layer-stacking structures have attracted widespread attention for their potential to enhance the charge transport performance of organic semiconductors and reduce the sensitivity of energetic molecules. Still, it lacks insights into such stacking. We conduct in this work a comprehensive understanding of 65 planar layer-stacked CHON-containing molecules based on intermolecular interaction. All the 59 hydrogenous molecules each always form HB in crystal packing, ascribed to the H atoms possessing the largest positive electrostatic potential extremes, and it requires negative ones against them to enhance intermolecular attraction and consolidate the planar layers. Meanwhile, the intralayer intermolecular interaction strength is not a decisive factor of the planar layer-stacking for either H-free or hydrogenous molecules, and its dependence on interlayer distance or packing coefficient is found, even though there seemingly exist some rough trends. It seems that we can hardly understand the planar layer-stacking based on CHON-containing alone, and further study covering other compositions is required.

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Section: Introductionmentioning

confidence: 73%

“…Notably, molecules containing exclusively O−H bonds appear rarely, with only one sample of KECYBU02. 41 3.1. Stacking of H-free Molecules.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 81%

Section: Stacking Of Hydrogenous Moleculesmentioning

confidence: 99%

Section: Data Collection and Objectsmentioning

confidence: 99%

See 3 more Smart Citations

Planar Layer-Stacking of CHON-Containing Molecules

Guo,

Xue,

Zuo

et al. 2024

Crystal Growth & Design

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Crystal Packing of Planar Organic Azide Molecules

Xue,

Zuo,

Guo

et al. 2024

Crystal Growth & Design

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Organic azides possess the potential for green primary explosives, gas generators, and propellants. This work focuses on the crystal packing of 34 planar organic azides and presents an understanding of their properties and performances. As the functional group of azides, −N 3 is wholly weakly charged, and individually, the outer, middle, and inner N atoms thereof are weakly negatively, rather strongly positively, and negatively charged, respectively. This weak polarity leads to weak intermolecular interactions, stemming from the generally lower packing coefficients and lower packing densities of azide crystals, compared with some typical hydrogen bond (HB)-containing nitro compounds. −N 3 is mostly lonely in crystal packing, as its outer N atom is seldom observed as an intermolecular HB acceptor, and the inner N atom acts as an intramolecular HB acceptor in only one case out of a total of 16. Introducing strong HB acceptor/donor groups to azides generally facilitates the enhancement of intermolecular interaction and molecular/crystal stability. Ascribed to the extremely low molecular stability, no evident dependence of impact sensitivity on molecular stacking mode is found for the whole azides. The top three azides with the lowest impact sensitivity all contain dense or moderately strong HBs, implying that HB introduction could be a strategy for enhancing the safety of azides.

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Characteristics of planar and planar layer-stacked CHON-containing molecules

Abstract: This paper unveils the characteristics of planar and planar layer-stacked CHON-containing molecules.

Cited by 2 publications

References 60 publications

Planar Layer-Stacking of CHON-Containing Molecules

Planar Layer-Stacking of CHON-Containing Molecules

Crystal Packing of Planar Organic Azide Molecules

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