Halogen Bonding in the Complexes of CH₃I and CCl₄ with Oxygen-Containing Halogen-Bond Acceptors

Abstract

Methyl iodine (CHI) and carbon tetrachloride (CCl) are both important volatile precursors for atmospheric ozone destruction. CHI and CCl can act as halogen bond donors to form molecular complexes with atmospheric organic species, such as 2,5-dihydrofuran, tetrahydrofuran, and acetone. This study characterized the halogen bonds in the CHI and CCl complexes using matrix isolation infrared spectroscopy and density functional theory calculations. With the combination of vibrational frequencies in spectra and the calculated interaction energies, frequencies and atoms-in-molecules analyses, we confirmed the formation of halogen-bonded complexes. CHI as a halogen-bond donor is comparable or slightly weaker than CCl, and furans involving ether oxygens are better halogen acceptors than acetone. The results help to understand the possibilities of formation of atmospheric molecular complexes that may influence the atmospheric chemical activities and enhance the aerosol formation.

The C–I···–O–N+ Halogen Bonds with Tetraiodoethylene and Aromatic N-Oxides

“…It has been previously observed in systems of small XB-donors displaying multiple XB-interactions that the presence of a second or third halogen bond can enhance the overall strengths of halogen bonds. [54][55][56] ). Our results show that tetraiodoethylene has not gained the attention it deserves in halogen bonding, and there remains a great deal to be explored in using tetraiodoethylene as a non-fluorinated halogen bond donor for supramolecular design.…”

Molecular interaction between MeOH and genistein during soy extraction

“…The ESP maps can present the distribution of the electron density. 36 The hydrogen atom of the OH group of genistein (Mulliken spin densities on H a , H b , H e ¼ 0.21-0.24 e À ) and MeOH (Mulliken spin density on H ¼ 0.20 e À ) show positive ESPs (blue color in Fig. 3), and these enables genistein, and MeOH to be a hydrogen bond donor.…”

Halogen Bonds Formed between Substituted Imidazoliums and N Bases of Varying N-Hybridization

“…As in H-bonds, electron donors/halogen acceptors can be varied, not only classical lone pairs, but π-bonds and aromatic systems [ 36 , 44 , 45 , 46 , 47 , 48 ], carbenes [ 49 ], σ-bonds [ 50 ], and even metal atoms [ 47 , 51 , 52 ]. Numerous studies [ 20 , 53 , 54 ] have led to a set of general rules concerning halogen bonds. There is a tendency for this bond to strengthen as one moves down the periodic table: Cl < Br < I; F is a reluctant participant.…”