Synthesis, X-ray characterization and computational Studies of N-imidazolyl and N-pyrazolyl pyrimidine derivatives

Autor:	Ignasi Mata, Elies Molins, Carolina Estarellas, Pere M. Deyà, Marta Torres, Angel García-Raso, Juan J. Fiol, Pablo Cañellas, Francisca M. Albertí, Antonio Frontera
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Chemistry Organic Chemistry Stacking Protonation Biochemistry Crystal Ab initio quantum chemistry methods Computational chemistry Drug Discovery Outer sphere electron transfer Non-covalent interactions Counterion Lone pair
Zdroj:	Tetrahedron. 68:2374-2382
ISSN:	0040-4020
DOI:	10.1016/j.tet.2012.01.023
Popis:	In this manuscript we report the synthesis and X-ray characterization of neutral 2-(1H-imidazol-1-yl)-pyrimidine (1), 2-(1H-pyrazol-1-yl)-pyrimidine (2) and 1-(2-pyrimidinyl)-1H-benzimidazole (3). We have also obtained crystals of the corresponding hydrochlorides of compounds 1 and 3. Finally, the outer sphere complex of protonated 2-(1H-imidazol-1-yl)-pyrimidine with [CoCl4]2− as counterion is described. In several charged structures interesting anion–π interactions determine the crystal packing. Moreover, in neutral systems some stacking interactions are governed by double lone pair–π interactions. High level ab initio calculations (RI-MP2/def2-TZVP) have been used to evaluate the noncovalent interactions observed in the solid state and the interplay between them.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1a3d6776ecec7575b80af81898ed91fe https://doi.org/10.1016/j.tet.2012.01.023 Zobrazit plný text záznamu Full Text from ScienceDirect