Halogen Bonding and Other Iodine Interactions in Crystals of Dihydrothiazolo(oxazino)quinolinium Oligoiodides from the Electron-Density Viewpoint

被引:52
作者
Bartashevich, Ekaterina V. [1 ]
Yushina, Irina D. [1 ]
Stash, Adam I. [2 ]
Tsirelson, Vladimir G. [3 ]
机构
[1] South Ural State Univ, Chelyabinsk 454080, Russia
[2] L Ya Karpov Inst Phys Chem, Moscow 103064, Russia
[3] DI Mendeleev Univ Chem Technol, Moscow 125047, Russia
基金
俄罗斯基础研究基金会;
关键词
EXPERIMENTAL CHARGE-DENSITY; INTERMOLECULAR INTERACTIONS; TOPOLOGICAL ANALYSIS; LOCALIZATION FUNCTION; DIFFRACTION DATA; MODEL; DISTRIBUTIONS; COMPLEXES; FEATURES; HETEROCYCLES;
D O I
10.1021/cg500958q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The spatial organization of electron density in dihydrothiazolo(oxazino)quinolinium crystals with oligoiodide anions of various structures has been studied on the basis of 3D periodic KohnSham calculations. The combination of QTAIMC and the analysis of one-electron potential and electrostatic potential has revealed the significant differences between halogen bonds (Type II interactions) and van der Waals (Type I) interactions for iodine atoms in crystalline environment. The traces of s-holes in electrostatic potential on the zero-flux interatomic surfaces of iodine moieties are the distinctive feature of halogen bonding; they do not appear in the weak van der Waals I...I interactions at all. The analysis of superposition of the gradient fields of the electron density and electrostatic potential has allowed detection of the strong electron redistribution along the oligoiodide chain [I-3...I-I...I-3]; the electron density is shifted from I-3 moiety to the cation via iodine molecule I-2 as a mediator. The quantitative relationship between the experimentally measured dissociation energy D-e(I-I/I...I) and the kinetic energy density at the bond critical point in the whole range of observed iodine interactions has been established.
引用
收藏
页码:5674 / 5684
页数:11
相关论文
共 100 条
[1]   The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388
[2]  
[Anonymous], 2011, CAMBRIDGE STRUCTURAL
[3]  
[Anonymous], CHEM HETEROCYCL COMP
[4]   A Green's function for the density [J].
Bader, RFW ;
Gatti, C .
CHEMICAL PHYSICS LETTERS, 1998, 287 (3-4) :233-238
[5]   PROPERTIES OF ATOMS IN MOLECULES - ATOMIC VOLUMES [J].
BADER, RFW ;
CARROLL, MT ;
CHEESEMAN, JR ;
CHANG, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) :7968-7979
[6]   VIRIAL FIELD RELATIONSHIP FOR MOLECULAR CHARGE DISTRIBUTIONS AND SPATIAL PARTITIONING OF MOLECULAR PROPERTIES [J].
BADER, RFW ;
BEDDALL, PM .
JOURNAL OF CHEMICAL PHYSICS, 1972, 56 (07) :3320-+
[7]   Characterizing the multiple non-covalent interactions in N, S-heterocycles-diiodine complexes with focus on halogen bonding [J].
Bartashevich, E. V. ;
Matveychuk, Y. V. ;
Troitskaya, E. A. ;
Tsirelson, V. G. .
COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2014, 1037 :53-62
[8]   Complex structure tri- and polyiodides of iodocyclization products of 2-allylthioquinoline [J].
Bartashevich, E. V. ;
Yushina, I. D. ;
Vershinina, E. A. ;
Slepukhin, P. A. ;
Kim, D. G. .
JOURNAL OF STRUCTURAL CHEMISTRY, 2014, 55 (01) :112-119
[9]   Atomic dipole polarization in charge-transfer complexes with halogen bonding [J].
Bartashevich, E. V. ;
Tsirelson, V. G. .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2013, 15 (07) :2530-2538
[10]  
Bartashevich E. V., 2012, 16 S INT INT CONF MO, P31