Interplay between N∙∙∙H, N∙∙∙X and π∙∙∙X interactions in the complex pairing of pyrazine with hypohalous acids: A NBO and QTAIM (quantum theory of atoms in molecules)  analysis

Zabardasti, Abedien; Tyula, Yunes Abbasi; Goudarziafshar, Hamid

doi:10.4314/bcse.v31i2.6

Cited by 6 publications

(2 citation statements)

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“…The presence of a σ hole on the iodine atoms of I 2 and HOI is known to promote halogen bonding, − likely with the NO 3 – anion. In this vein, we propose that IONO 2 is formed in the gas phase via reactions and . Supporting I 2 and HOI in the ionization region is the observation in mass spectra (Figure b) of I 2 – , OI – , (H 2 O)OI – , (HOI)I – , and (HOI)OI – .…”

Section: Resultsmentioning

confidence: 99%

Role of Gas-Phase Halogen Bonding in Ambient Chemical Ionization Mass Spectrometry Utilizing Iodine

Ganske

Wingen

Perraud

et al. 2019

ACS Earth Space Chem.

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Ambient ionization processes are becoming more widely used for the measurement of atmospherically relevant particles and gases. We report here ambient ionization mass spectra utilizing a commercial tincture of iodine and a piezoelectric discharge gun (PDG) to generate the ionizing reagents. Analytes include Cl 2 , Br 2 , HNO 3 , the C 1 −C 9 series of saturated monocarboxylic acids, benzoic acid, 2,2-dimethylpropanoic acid, 9-decenoic acid, and trichloroacetic acid. While Cl 2 and Br 2 form the [M + I] − iodide adducts, HNO 3 and the organic acids show unexpected peaks corresponding to [2M − 2H + I] −. For HNO 3 , the new ion formed is interpreted as the [NO 3 − •••IONO 2 ] complex, where IONO 2 is likely formed upon reaction of HOI with gaseous NO 3 −. Similarly, for the organic acids, the [2M − 2H + I] − peaks are interpreted as [RC(O)O − •••IOC(O)R] complexes formed by association of RC(O)O − with acyl hypoiodites [RC(O)OI]. It is proposed that the association of (1) Cl 2 and Br 2 with I − , (2) IONO 2 with NO 3 − ions, and (3) RC(O)OI with carboxylate ions occurs via non-covalent halogen bonding. The results suggest the possibility that halogen bonding may play a role in chemical transformations in the atmosphere, particularly in particles where concentrations of iodinated species may be significant.

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Section: Resultsmentioning

confidence: 99%

Role of Gas-Phase Halogen Bonding in Ambient Chemical Ionization Mass Spectrometry Utilizing Iodine

Ganske

Wingen

Perraud

et al. 2019

ACS Earth Space Chem.

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“…Theoretical studies on intermolecular interactions between HOX and a variety of chemical species have been conducted [96–105] . A majority of the studies utilized Møller–Plesset second‐order perturbation (MP2) theory with Dunning basis sets.…”

Section: Introductionmentioning

confidence: 99%

The HOX⋯SO₂ (X=F, Cl, Br, I) Binary Complexes: Implications for Atmospheric Chemistry

et al. 2020

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Sulfur dioxide and hypohalous acids (HOX, X=F, Cl, Br, I) are ubiquitous molecules in the atmosphere that are central to important processes like seasonal ozone depletion, acid rain, and cloud nucleation. We present the first theoretical examination of the HOX⋯SO2 binary complexes and the associated trends due to halogen substitution. Reliable geometries were optimized at the CCSD(T)/aug‐cc‐pV(T+d)Z level of theory for HOF and HOCl complexes. The HOBr and HOI complexes were optimized at the CCSD(T)/aug‐cc‐pV(D+d)Z level of theory with the exception of the Br and I atoms which were modeled with an aug‐cc‐pwCVDZ‐PP pseudopotential. 27 HOX⋯SO2 complexes were characterized and the focal point method was employed to produce CCSDT(Q)/CBS interaction energies. Natural Bond Orbital analysis and Symmetry Adapted Perturbation Theory were used to classify the nature of each principle interaction. The interaction energies of all HOX⋯SO2 complexes in this study ranged from 1.35 to 3.81 kcal mol−1. The single‐interaction hydrogen bonded complexes spanned a range of 2.62 to 3.07 kcal mol−1, while the single‐interaction halogen bonded complexes were far more sensitive to halogen substitution ranging from 1.35 to 3.06 kcal mol−1, indicating that the two types of interactions are extremely competitive for heavier halogens. Our results provide insight into the interactions between HOX and SO2 which may guide further research of related systems.

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Ab initio investigation of the competition of pnicogen, halogen, and hydrogen bonds resulting from the interactions between cyanophosphine and hypohalous acids

Moradkhani,

Naghipour,

Tyula

2023

J Mol Model

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Interplay between N∙∙∙H, N∙∙∙X and π∙∙∙X interactions in the complex pairing of pyrazine with hypohalous acids: A NBO and QTAIM (quantum theory of atoms in molecules) analysis

Cited by 6 publications

References 46 publications

Role of Gas-Phase Halogen Bonding in Ambient Chemical Ionization Mass Spectrometry Utilizing Iodine

Role of Gas-Phase Halogen Bonding in Ambient Chemical Ionization Mass Spectrometry Utilizing Iodine

The HOX⋯SO₂ (X=F, Cl, Br, I) Binary Complexes: Implications for Atmospheric Chemistry

Ab initio investigation of the competition of pnicogen, halogen, and hydrogen bonds resulting from the interactions between cyanophosphine and hypohalous acids

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Interplay between N∙∙∙H, N∙∙∙X and π∙∙∙X interactions in the complex pairing of pyrazine with hypohalous acids: A NBO and QTAIM (quantum theory of atoms in molecules) analysis

Cited by 6 publications

References 46 publications

Role of Gas-Phase Halogen Bonding in Ambient Chemical Ionization Mass Spectrometry Utilizing Iodine

Role of Gas-Phase Halogen Bonding in Ambient Chemical Ionization Mass Spectrometry Utilizing Iodine

The HOX⋯SO2 (X=F, Cl, Br, I) Binary Complexes: Implications for Atmospheric Chemistry

Ab initio investigation of the competition of pnicogen, halogen, and hydrogen bonds resulting from the interactions between cyanophosphine and hypohalous acids

Contact Info

Product

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The HOX⋯SO₂ (X=F, Cl, Br, I) Binary Complexes: Implications for Atmospheric Chemistry