Two different products from the reaction of 1-aryl-5-chloro-3-methyl-1H-pyrazole-4-carbaldehyde with cyclohexylamine when the aryl substituent is phenyl or pyridin-2-yl: hydrogen-bonded sheets versus dimers

Jessica Orrego Hernez; Jaime Portilla; Justo Cobo; Christopher Glidewell

首页> 外文期刊>Acta crystallographica. Section C, Structural chemistry. >Two different products from the reaction of 1-aryl-5-chloro-3-methyl-1H-pyrazole-4-carbaldehyde with cyclohexylamine when the aryl substituent is phenyl or pyridin-2-yl: hydrogen-bonded sheets versus dimers

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Two different products from the reaction of 1-aryl-5-chloro-3-methyl-1H-pyrazole-4-carbaldehyde with cyclohexylamine when the aryl substituent is phenyl or pyridin-2-yl: hydrogen-bonded sheets versus dimers

机译：当芳基取代基为苯基或吡啶-2-基时，1-芳基-5-氯-3-甲基-1H-吡唑-4-甲醛与环己胺反应生成的两种不同产物：氢键合的片层与二聚体

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Cyclohexylamine reacts with 5-chloro-3-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde to give 5-cyclohexylamino-3-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde, C16H20N4O, (I), formed by nucleophilic substitution, but with 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde the product is (Z)-4-[(cyclohexylamino)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, C17H21N3O, (II), formed by condensation followed by hydrolysis. Compound (II) crystallizes with Z′ = 2, and in one of the two independent molecular types the cyclohexylamine unit is disordered over two sets of atomic sites having occupancies of 0.65?(3) and 0.35?(3). The vinylogous amide portion in each compound shows evidence of electronic polarization, such that in each the O atom carries a partial negative charge and the N atom of the cyclohexylamine portion carries a partial positive charge. The molecules of (I) contain an intramolecular N—H...N hydrogen bond, and they are linked by C—H...O hydrogen bonds to form sheets. Each of the two independent molecules of (II) contains an intramolecular N—H...O hydrogen bond and each molecular type forms a centrosymmetric dimer containing one R22(4) ring and two inversion-related S(6) rings.

机译：环己胺与5-氯-3-甲基-1-（吡啶-2-基）-1H-吡唑-4-甲醛反应生成5-环己基氨基-3-甲基-1-（吡啶-2-基）-1H-吡唑-4-甲醛，C16H20N4O，（I），通过亲核取代形成，但与5-氯-3-甲基-1-苯基-1H-吡唑-4-甲醛反应生成的是（Z）-4-[[（环己基氨基））亚甲基] -3-甲基-1-苯基-1H-吡唑-5（4H）-1，C17H21N3O，（II），通过缩合然后水解形成。化合物（II）以Z′＝ 2结晶，并且在两种独立分子类型之一中，环己胺单元在两组具有0.65π（3）和0.35π（3）的原子位点上是无序的。每个化合物中的乙烯基酰胺部分显示出电子极化的迹象，因此每个O原子带有部分负电荷，而环己胺部分的N原子带有部分正电荷。（I）的分子包含分子内的NH ... N氢键，并且它们通过CH ... O氢键连接以形成片。（II）的两个独立分子中的每一个均包含分子内N-H ... O氢键，并且每种分子类型形成一个包含一个R22（4）环和两个与转化相关的S（6）环的中心对称二聚体。

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《Acta crystallographica. Section C, Structural chemistry.》 |2015年第5期|共6页
作者
Jessica Orrego Hernez; Jaime Portilla; Justo Cobo; Christopher Glidewell;
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正文语种 eng
中图分类晶体学;
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pharmaceutical compounds; condensation reaction; nucleophilic substitution; crystal structure; hydrogen bonding;

机译：药物化合物;缩合反应;亲核取代;晶体结构;氢键;

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Two different products from the reaction of 1-aryl-5-chloro-3-methyl-1H-pyrazole-4-carbaldehyde with cyclohexylamine when the aryl substituent is phenyl or pyridin-2-yl: hydrogen-bonded sheets versus dimers

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