Comparative Structural Study of Three Tetrahalophthalic Anhydrides: Recognition of X•••O(anhydride) Halogen Bond and πh•••O(anhydride) Interaction

被引:2
作者
Baykov, Sergey V. [1 ]
Semenov, Artem V. [2 ,3 ]
Katlenok, Eugene A. [1 ]
Shetnev, Anton A. [4 ]
Bokach, Nadezhda A. [1 ]
机构
[1] St Petersburg State Univ, Inst Chem, 7-9 Univ Skaya Nab, St Petersburg 199034, Russia
[2] MIREA Russian Technol Univ, MV Lomonosov Inst Fine Chem Technol, 86 Vernadskogo Pr, Moscow 119571, Russia
[3] Shemyakin Ovchinnikov Inst Bioorgan Chem, 16-10 Miklukho Maklaya St, Moscow 117997, Russia
[4] Yaroslavl State Pedag Univ, Pharmaceut Technol Transfer Ctr, 108 Respublikanskaya St, Yaroslavl 150000, Russia
来源
MOLECULES | 2021年 / 26卷 / 11期
基金
俄罗斯科学基金会;
关键词
noncovalent interactions; halogen bond; tetrahalophthalic anhydrides; X-ray diffraction studies; computational studies; CHARGE-TRANSFER COMPLEX; TETRACHLOROPHTHALIC ANHYDRIDE; PERTURBATION-THEORY; MOLECULAR-STRUCTURES; DISPERSION; CRYSTAL; FERROELECTRICITY; APPROXIMATION; GRADIENT; ELECTRON;
D O I
10.3390/molecules26113119
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Structures of three tetrahalophthalic anhydrides (TXPA: halogen = Cl (TCPA), Br (TBPA), I (TIPA)) were studied by X-ray diffraction, and several types of halogen bonds (HaB) and lone pair center dot center dot center dot pi-hole (lp center dot center dot center dot pi h) contacts were revealed in their structures. HaBs involving the central oxygen atom of anhydride group (further X center dot center dot center dot O(anhydride) were recognized in the structures of TCPA and TBPA. In contrast, for the O(anhydride) atom of TIPA, only interactions with the pi system (pi-hole) of the anhydride ring (further lp(O)center dot center dot center dot pi h) were observed. Computational studies by a number of theoretical methods (molecular electrostatic potentials, the quantum theory of atoms in molecules, the independent gradient model, natural bond orbital analyses, the electron density difference, and symmetry-adapted perturbation theory) demonstrated that the X center dot center dot center dot O(anhydride) contacts in TCPA and TBPA and lp(O)center dot center dot center dot pi h in TIPA are caused by the packing effect. The supramolecular architecture of isostructural TCPA and TBPA was mainly affected by X center dot center dot center dot O(acyl) and X center dot center dot center dot X HaBs, and, for TIPA, the main contribution provided I center dot center dot center dot I HaBs.
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页数:15
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