Orthogonal hydrogen/halogen bonding in 1-(2-methoxyphenyl)-1H-imidazole-2(3H)-thione-I2 adduct: an experimental and theoretical study.
The molecular complex between 1-(2-methoxyphenyl)-1H-imidazole-2(3H)-thione (Hmim(OMe)) and iodine (I2) was investigated. Single crystal of [(Hmim(OMe))I2] adduct was grown by slow evaporation technique from chloroform at room temperature. Spectroscopic techniques such as FT-IR and Raman techniques, as well as elemental and thermal analysis were used to characterize the complex. The crystal structure shows that the formed adduct stabilized by two noncovalent interactions, namely, hydrogen bond (HB) and halogen bond (XB). Orthogonal HB/XB associated with iodine atom (I) was observed and fully characterized. The ability of iodine to behave as hydrogen bond acceptor and halogen bond donor was held responsible for the orthogonal HB/XB presence. In addition, the structure of Hmim(OMe)I2 was investigated theoretically using MP2/aug-cc-pVDZ level of theory. Natural bond orbital analysis (NBO) was used to investigate the molecular orbitals interactions and orbitals stabilization energies.
Biotechnology and Fish Processing Department, Faculty of Aquatic and Fisheries Sciences, Kafrelsheikh University, 33516 Kafr ElSheikh, Egypt; Nanochemistry Laboratory, Chemistry Department, Faculty of Science, Kafrelsheikh University, 33516 Kafr ElSheikh, Egypt. Electronic address: h.elsheshtawy@fsh.kfs.edu.eg.
Hamdy S
HS
El-Sheshtawy
Chemistry Department, Faculty of Science, Kafrelsheikh University, 33516 Kafr ElSheikh, Egypt; Chemistry Department, Faculty of Science, Taif University, Taif, Saudi Arabia.
Mohamed M
MM
Ibrahim
Chemistry Department, Faculty of Science, Kafrelsheikh University, 33516 Kafr ElSheikh, Egypt; Nanochemistry Laboratory, Chemistry Department, Faculty of Science, Kafrelsheikh University, 33516 Kafr ElSheikh, Egypt.
Ibrahim
I
El-Mehasseb
Chemistry Department, Faculty of Science, Kafrelsheikh University, 33516 Kafr ElSheikh, Egypt; Nanochemistry Laboratory, Chemistry Department, Faculty of Science, Kafrelsheikh University, 33516 Kafr ElSheikh, Egypt.
Maged
M
El-Kemary
D003460:Crystallization; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D013816:Thermodynamics; D013871:Thiones / Q000737:chemistry*
C000604641:1-(2-methoxyphenyl)-1H-imidazole-2(3H)-thione; D007093:Imidazoles; D013871:Thiones; D007455:Iodine
1-(2-Methoxyphenyl)-1H-imidazole-2(3H)-thione; Halogen bond; Hydrogen bond; Theoretical calculations; X-ray crystal structure