Effects of Supramolecular Architecture on Halogen Bonding between Diiodine and Heteroaromatic N-Oxides
| Autor: | Sergiy V. Rosokha, Alex Sons, Matthias Zeller, Yakov P. Nizhnik |
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| Rok vydání: | 2018 |
| Předmět: |
Halogen bond
010405 organic chemistry Supramolecular chemistry General Chemistry Dihedral angle 010402 general chemistry Condensed Matter Physics 01 natural sciences 0104 chemical sciences Adduct chemistry.chemical_compound Crystallography chemistry Acridine Pyridine Halogen Molecule General Materials Science |
| Zdroj: | Crystal Growth & Design. 18:1198-1207 |
| ISSN: | 1528-7505 1528-7483 |
| DOI: | 10.1021/acs.cgd.7b01734 |
| Popis: | Cocrystallization of diiodine with a series of heteroaromatic N-oxides produced three types of halogen-bonded associates: (a) alternating chains comprising I2 molecules bridged by oxygen atoms of N-oxides of pyridine, quinoline, or 4-methylpyridine; (b) discrete 2:1 complexes, in which diiodine links a pair of acridine N-oxide molecules; and (c) amphoteric 1:1 adducts, in which one end of each diiodine molecule is halogen-bonded to N-oxide of 4-methoxypyridine or 4-chloroquinoline, and another diiodine’s end forms contacts with the other I2 molecules. In all cases, halogen bonds between diiodine and N-oxides are characterized by nearly linear I–I···O angles, close to perpendicular dihedral C–N–O···I angles and N–O···I angles of about 110°. The halogen bond length in the 1:1 adducts is about 0.3 A shorter than those in the 2:1 associates and in the infinite chains. Computational analyses confirmed that the variations in I···O separations are related predominantly to the distinct effects of halogen bond com... |
| Databáze: | OpenAIRE |
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