Hydrogen-bonded structures of the 1:1 and 1:2 compounds of chloranilic acid with pyrrolidin-2-one and piperidine-2-one
Hydrogen-bonded structures of the 1:1 and 1:2 compounds of chloranilic acid with pyrrolidin-2-one and piperidine-2-one
复制标题
氯苯甲酸与吡咯烷-2-酮和哌啶-2-酮的1:1和1:2化合物的氢键结构
DOI：
10.1107/s0108270111048165
复制
发表时间：
2011
期刊：
影响因子：
--
通讯作者：
Kazuma Gotohand Hiroyuki Ishida
中科院分区：
文献类型：
--
作者：
熊谷嘉晃;他;Kazuma Gotohand Hiroyuki Ishida
在氯冉酸的四种化合物中（2，5-二氯-3，6-二羟基环己-2，5-二烯-1，4-二酮）与吡咯烷-2-酮和哌啶-2-酮，即氯冉酸-吡咯烷-2-酮（1/1），C6 H2 Cl 2 O 4·C4 H7 NO，（I），氯冉酸-吡咯烷-2-酮（1/2），C6 H2 Cl 2 O 4·2C 4 H7 NO，（II），氯冉酸-哌啶-2-酮（1/1），C6 H2 Cl 2 O 4·C5 H9 NO，（III）和氯冉酸-哌啶-2-酮（1/2），C6 H2 Cl 2 O 4·2C 5 H9 NO，（IV），两组分间最短的相互作用是O-H-O氢键，它是晶体结构中主要的分子间相互作用。在（II）、（III）和（IV）中，氯冉酸分子位于反转中心附近。 对于（III），这需要存在两个独立的酸分子。在（I）中，在不对称单元中存在两个式单元。O → O距离分别为2.4728（11）和2.4978（11）in（I），2.5845（11）in（II），2.6223（11）和2.5909（10）in（III），以及2.4484（10）in（IV）。 在（IV）的氢键中，H原子在两个位置上是无序的，位置占有率为0.44（3）和0.56（3）。 这表明酸和碱之间发生了部分质子转移，形成了离子对。在（I）和（II）中，N-H-O氢键（二级分子间相互作用）将吡咯烷-2-酮分子连接成二聚体，而在（III）和（IV）中，这些氢键分别连接酸和碱以提供三维和二维氢键网络。
In the four compounds of chloranilic acid (2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione) with pyrrolidin-2-one and piperidin-2-one, namely, chloranilic acid–pyrrolidin-2-one (1/1), C6H2Cl2O4·C4H7NO, (I), chloranilic acid–pyrrolidin-2-one (1/2), C6H2Cl2O4·2C4H7NO, (II), chloranilic acid–piperidin-2-one (1/1), C6H2Cl2O4·C5H9NO, (III), and chloranilic acid–piperidin-2-one (1/2), C6H2Cl2O4·2C5H9NO, (IV), the shortest interactions between the two components are O—H⋯O hydrogen bonds, which act as the primary intermolecular interaction in the crystal structures. In (II), (III) and (IV), the chloranilic acid molecules lie about inversion centres. For (III), this necessitates the presence of two independent acid molecules. In (I), there are two formula units in the asymmetric unit. The O⋯O distances are 2.4728 (11) and 2.4978 (11) Å in (I), 2.5845 (11) Å in (II), 2.6223 (11) and 2.5909 (10) Å in (III), and 2.4484 (10) Å in (IV). In the hydrogen bond of (IV), the H atom is disordered over two positions with site occupancies of 0.44 (3) and 0.56 (3). This indicates that proton transfer between the acid and base has partly taken place to form ion pairs. In (I) and (II), N—H⋯O hydrogen bonds, the secondary intermolecular interactions, connect the pyrrolidin-2-one molecules into a dimer, while in (III) and (IV) these hydrogen bonds link the acid and base to afford three- and two-dimensional hydrogen-bonded networks, respectively.