Vahdani Alviri Banafsheh, Pourayoubi Mehrdad, Farhadipour Abolghasem, Nečas Marek, Bertolasi Valerio
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran.
Department of Chemistry, Masaryk University, Kotlarska 2, Brno CZ-6113, Czech Republic.
Acta Crystallogr C Struct Chem. 2018 Dec 1;74(Pt 12):1610-1621. doi: 10.1107/S2053229618014006. Epub 2018 Nov 13.
The crystal structures of N,N'-(cyclohexane-1,4-diyl)bis(O,O'-diphenylphosphoramide), CHNOP or (CHO)P(O)(1-NH)(CH)(4-NH)P(O)(OCH), (I), and N,N'-(1,4-phenylene)bis(O,O'-dimethylthiophosphoramide), CHNOPS or (CHO)P(S)(1-NH)(CH)(4-NH)P(S)(OCH), (II), have been investigated. In the structure of (I), with an (O)(N)P(O) skeleton, two symmetry-independent phosphoramide molecules are linked through N-H...O=P hydrogen bonds. In the structure of (II), with an (O)(N)P(S) skeleton, the ester O atoms take part in N-H...O-C hydrogen bonds as acceptors; the P=S groups do not participate in hydrogen-bonding interactions. The strengths of these hydrogen bonds were evaluated, using quantum chemical calculations with the GAUSSIAN09 software package at the B3LYP/6-311G(d,p) level of theory. For this, LP(O) to σ*(NH) charge transfers were studied, according to the second-order perturbation theory in natural bond orbital (NBO) methodology, for a three-component cluster of hydrogen-bonded molecules for both structures, including all of the independent N-H...O hydrogen bonds observed in the crystal packing. The details of the intermolecular interactions were studied by Hirshfeld surface maps and two-dimensional fingerprint plots.
已对N,N'-（环己烷-1,4-二基）双（O,O'-二苯基磷酰胺），即CHNOP或(CHO)P(O)(1-NH)(CH)(4-NH)P(O)(OCH)，（I），以及N,N'-（1,4-亚苯基）双（O,O'-二甲基硫代磷酰胺），即CHNOPS或(CHO)P(S)(1-NH)(CH)(4-NH)P(S)(OCH)，（II）的晶体结构进行了研究。在（I）的结构中，具有(O)(N)P(O)骨架，两个对称独立的磷酰胺分子通过N-H...O=P氢键相连。在（II）的结构中，具有(O)(N)P(S)骨架，酯O原子作为受体参与N-H...O-C氢键；P=S基团不参与氢键相互作用。使用GAUSSIAN09软件包在B3LYP/6-311G(d,p)理论水平下通过量子化学计算评估了这些氢键的强度。为此，根据自然键轨道（NBO）方法中的二阶微扰理论，对两种结构的氢键分子的三组分簇进行了LP(O)到σ*(NH)电荷转移的研究，包括在晶体堆积中观察到的所有独立的N-H...O氢键。通过Hirshfeld表面图和二维指纹图谱研究了分子间相互作用的细节。
