Role of intermolecular interactions in formation of mono- and diaminopyridine crystals: study from the energetic viewpoi
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ORIGINAL RESEARCH
Role of intermolecular interactions in formation of monoand diaminopyridine crystals: study from the energetic viewpoint Irina S. Konovalova 1,2 & Ekaterina N. Muzyka 2 & Victoriya V. Urzhuntseva 3 & Svitlana V. Shishkina 1,2,3 Received: 13 July 2020 / Accepted: 20 August 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract The regularities of crystal structure organization in a series of mono- and diaminopyridines possessing biological activities were studied using an approach based on comparison of interaction energies between molecules calculated by ab initio quantum chemical method. The presence of the pyridine nitrogen atom causes the formation of N–H…Npyr hydrogen bond which is the strongest in all the studied structures. Being amphiphilic in hydrogen bond formation, the amino group possesses acceptor properties only in meta-position to the pyridine nitrogen atom in mono-aminopyridines. The presence of the two amino groups results in increasing of acceptor properties of both ones. The N–H…Nlp hydrogen bonds bind primary BSM (basic structural motif) in the structures of 2,5-diaminopyridine, 2,4-diaminopyridine and 3,4-diamonpyridine and form the primary BSM alongside with N–H…Npyr hydrogen bond in the structure of 2,3-diaminopyridine. The helical primary basic structural motif and double helical secondary basic structural motif in the 2,3-diaminopyridine crystal structure are very similar to the DNA helix and double helix. Keywords Aminopyridine . Crystal packing . Hydrogen bond . Pairwise interaction energy . Energy vector diagram . Quantum-chemical calculations
Introduction Formation of various systems of the molecule arrangement in a crystal is the result of the molecule ability to participate in different types of specific intermolecular interactions caused by the presence of different functional groups in a molecule. The knowledge about definite functional group ability to participate in intermolecular interactions is very important from the viewpoint of supramolecular synthon conception, which is the basis of modern crystal engineering [1–3]. According to Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11224-020-01625-6) contains supplementary material, which is available to authorized users. * Svitlana V. Shishkina [email protected] 1
SSI “Institute for Single Crystals”, National Academy of Science of Ukraine, 60 Nauky Ave., Kharkiv 61001, Ukraine
2
National University of Radio Electronics, 14 Nauky Ave., Kharkiv 61001, Ukraine
3
V. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv 61077, Ukraine
this conception, molecules form some stable motifs in the crystal phase due to a set of standard, mostly strong, intermolecular interactions. Hence, regulating the ability of the molecule to form certain types of intermolecular interactions is an appropriate tool used for designing the supramolecular architecture of crystals. The benzene, its heterocyclic analogues and the simplest deriv
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