The nature of p-hole interactions between iodide anions and quinoid rings in the crystalline state

被引：9

作者：

Milasinovic, Valentina ^{[1
]}

Vukovic, Vedran ^{[2
]}

Krawczuk, Anna ^{[3
]}

Molcanov, Kresimir ^{[1
]}

Hennig, Christoph ^{[4
,5
]}

Bodensteiner, Michael ^{[2
]}

机构：

[1] Rudjer Boskovic Inst, Dept Phys Chem, Bijenicka 54, Zagreb 10000, Croatia

[2] Univ Regensburg, Univ Str 31, D-93053 Regensburg, Germany

[3] Univ Gottingen, Inst Anorgan Chem, Tammanstr 4, D-37077 Gottingen, Germany

[4] European Synchrotron Radiat Facil, Rossendori Beamline BM20, 71 Ave Martyrs, F-38043 Grenoble, France

[5] Helmholz Zentrum Dresden Rosendori, Inst Resource Ecol, Baurtner Landstr 400, D-01328 Dresden, Germany

来源：

IUCRJ | 2023年 / 10卷

关键词：

pi-hole interactions; charge transfer; quinone; charge density; Atoms In Molecule; analysis; CHARGE-DENSITY ANALYSIS; ELECTRONIC-STRUCTURE; SOLID-STATE; BASIS-SETS; COMPLEXES; SIGMA; HALOGEN; QUALITY; SURFACE; BOND;

D O I：

10.1107/S2052252523000052

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The investigated co-crystal of 3-chloro-N-methylpyridinium iodide with tetrabromoquinone (3-Cl-N-MePy center dot I center dot Br(4)Q) reveals a pi-hole interaction between an iodide anion and a quinoid ring involving an n -> pi* charge transfer. The quinoid ring has a partial negative charge (estimated to be in the range 0.08-0.11e) and a partial radical character, which is related to the black colour of the crystals (crystals of neutral tetrabromoquinone are yellow). A detailed X-ray charge density study revealed two symmetry-independent bond critical points between the iodide anions and carbon atoms of the ring. Their maximum electron density of 0.065 e angstrom(-3) was reproduced by quantum chemical modelling. The energy of the interaction is estimated to be -11.16 kcal mol(-1), which is comparable to the strength of moderate hydrogen bonding (about -10 kcal mol(-1)); it is dominantly electrostatic in nature, with a considerable dispersion component.

引用

页码：156 / 163

页数：8

共 48 条

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