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

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• 作者：Marta Torres^a ; Pablo Cañ ; ellas^a ; Carolina Estarellas^a ; Angel Garcí ; a-Raso^a ; ^{angel.garcia-raso@uib.es} ; Juan J. Fiol^a ; Francisca M. Albertí ; ^a ; Antonio Frontera^a ; ^{toni.frontera@uib.es} ; Elies Molins^b ; Ignasi Mata^b ; Pere M. Deyà ; ^a
• 关键词：Pyrimidines ; Imidazole and benzimidazole ; Ab initio calculations ; X-ray crystal structures ; Anion&ndash ; ¦Ð interactions
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：11 March, 2012
• 年：2012
• 卷：68
• 期：10
• 页码：2374-2382
• 全文大小：1122 K

文摘

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?/sup> as counterion is described. In several charged structures interesting anion-¦Ð interactions determine the crystal packing. Moreover, in neutral systems some stacking interactions are governed by double lone pair-¦Ð 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.}