3,6-Diamino-1,2,4,5-tetrazine: an example of strong intermolecular hydrogen bonding

Krieger, Claus; Fischer, Hans; Neugebauer, F. A.

doi:10.1107/s0108270187092011

Cited by 10 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…10 compounds are planar layer-stacked and coded as FITXIP, WANDUL, PMELIM, DAYBIO, CYURAC03, TATNBZ, RAVSOW, BARBOL, CEHQEM and VUGSIZ (see their chemical names in S3 of Supporting Information). It exhibits a limitation in the number of the D 2 h and D 3 h molecules stacked in the planar layer style.…”

Section: Resultsmentioning

confidence: 99%

Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D_2h and D_3h Molecules in Planar Layer-Stacked Crystals

Liu

Rong

et al. 2021

Crystal Growth & Design

View full text Add to dashboard Cite

The molecular structure and stacking mode relationship is the core of creating planar layer-stacked materials by crystal engineering. However, it remains highly challenging to clarify the relationship. By exhaustively extracting 50 compounds with D 2h or D 3h molecular point groups from the Cambridge Structural Database, we study in this work, the characteristics of planar layer-stacked molecules and those of others for comparison. For a hydrogenous molecule, it requires both a strong donor and acceptor of hydrogen bonds (HBs) therein and both large positive and negative electrostatic potential extremes (e.g., ≥35 kcal/mol at the theoretical level of B3LYP/6-311G(d)) situated on its edge for planar layer stacking, while regarding the H free molecules stacked in planar layers, they are prone to be sparsely arranged, and the intralayer intermolecular interactions belong to weak halogen bonding or other weak van der Waals attraction, with rather small electrostatic potential extremes on their edges and/or faces. Additionally, we first propose the definitions of six types of stacking modes to scientifically and exactly classify them based on the relative orientations and arrangement of molecular planes in the crystal. Accordingly, a strategy for constructing planar layer stacking with strong HBs is proposed. This work is expected to benefit the crystal engineering of planar layer-stacked materials.

show abstract

Section: Resultsmentioning

confidence: 99%

Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D_2h and D_3h Molecules in Planar Layer-Stacked Crystals

Liu

Rong

et al. 2021

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…BTAT crystallises in the space group Pna2 1 with one molecule in the asymmetric unit. The planar geometry reported for 3,6-diamino-1,2,3,5-tetrazine [46] is retained in the structure of BTAT. The two trinitroethyl groups bonded to the sp 2 -type amino nitrogen atoms are oriented trans to each other and are located on different sides of the tetrazine plane (Fig.…”

Section: Crystal Structure Analysismentioning

confidence: 86%

Development and Testing of Energetic Materials: The Concept of High Densities Based on the Trinitroethyl Functionality

Göbel

Klapötke

2009

Adv Funct Materials

212

116

View full text Add to dashboard Cite

The development of new energetic materials is an emerging area of materials chemistry facilitated by a worldwide need to replace materials used at present, due to environmental considerations and safety requirements, while at the same time securing high performance. The development of such materials is complex, owing to the fact that several different and apparently mutually exclusive material properties have to be met in order for a new material to become widely accepted. In turn, understanding the basic principles of structure property relationships is highly desirable, as such an understanding would allow for a more rational design process to yield the desired properties. This article covers the trinitroethyl functionality and its potential for the design of next generation energetic materials, and describes relevant aspects of energetic materials chemistry including theoretical calculations capable of reliably predicting material properties. The synthesis, characterization, energetic properties, and structure property relationships of several new promising compounds displaying excellent material properties are reported with respect to different kinds of applications and compared to standard explosives currently used. Based on a review of trinitroethyl‐containing compounds available in the literature, as well as this new contribution, it is observed that high density can generally be obtained in a more targeted manner in energetic materials taking advantage of noncovalent bonding interactions, a prerequisite for the design of next generation energetic materials.

show abstract

“…11 Figure 4 illustrates six π-conjugated energetic molecules, among which ICM-101 34 and NTO, 35 DAAF 36 and DAAzF, 37 More attention is paid to the planar layer π−π stacking, because it has been widely verified to be beneficial to low impact sensitivity or impact insensitivity. [9][10][11]14 Here, four planar layer-stacked compounds of RAVSOW, 40 CYUR-AC03, 41 FITXIP, 42 and TATNBZ (TATB) 31 are adopted for discussing the dependence of the characteristics of Hirshfeld surface and interlayered distance. After all, the interlayered distance governs the sliding barrier 43 and further the impact sensitivity.…”

Section: Applicationmentioning

confidence: 99%

Hirshfeld Surface Method and Its Application in Energetic Crystals

Gou

et al. 2021

Crystal Growth & Design

View full text Add to dashboard Cite

Understanding intermolecular interactions is fundamental to understanding the molecular stacking structures and some properties of energetic crystals, such as density, energy, mechanics, and sensitivity. The Hirshfeld surface method is a straightforward tool to reveal intermolecular interactions and nowadays has become increasingly popular in the field of energetic materials. This article highlights a wide range of applications of this method in describing intermolecular interactions including hydrogen bonding, π-stacking, halogen bonding, and lone pair−π (n−π) stacking, and molecular stacking patterns, and in predicting shear sliding characteristic and further impact sensitivity. Meanwhile, the roughness of the quantitative description of intermolecular interaction strength of the method, as a main shortcoming, is pointed out herein. Thus, this work is expected to guide the right and full use of the method. Besides, we present a perspective about using the Hirshfeld surface method to rapidly screen the molecular stacking mode and further impact sensitivity; thus, the fast screening of the two most important properties can be implemented, in combination with the existing mature energy prediction methods based on components. Thereby, a more reliable prediction procedure with an additional consideration of molecular stacking pattern will be produced, setting a basis for data-driven and crystal engineering research of energetic materials.

show abstract

3,6-Diamino-1,2,4,5-tetrazine: an example of strong intermolecular hydrogen bonding

Cited by 10 publications

References 0 publications

Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D_2h and D_3h Molecules in Planar Layer-Stacked Crystals

Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D_2h and D_3h Molecules in Planar Layer-Stacked Crystals

Development and Testing of Energetic Materials: The Concept of High Densities Based on the Trinitroethyl Functionality

Hirshfeld Surface Method and Its Application in Energetic Crystals

Contact Info

Product

Resources

About

3,6-Diamino-1,2,4,5-tetrazine: an example of strong intermolecular hydrogen bonding

Cited by 10 publications

References 0 publications

Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D2h and D3h Molecules in Planar Layer-Stacked Crystals

Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D2h and D3h Molecules in Planar Layer-Stacked Crystals

Development and Testing of Energetic Materials: The Concept of High Densities Based on the Trinitroethyl Functionality

Hirshfeld Surface Method and Its Application in Energetic Crystals

Contact Info

Product

Resources

About

Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D_2h and D_3h Molecules in Planar Layer-Stacked Crystals

Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D_2h and D_3h Molecules in Planar Layer-Stacked Crystals