On the nature of halogen bonded complexes between carbonyl bases and chlorotrifluoromethane

Zierkiewicz, Wiktor; Bieńko, Dariusz C.; Michalska, Danuta; Zeegers‐Huyskens, Th.

doi:10.1007/s00214-015-1706-7

Cited by 7 publications

(4 citation statements)

References 73 publications

(96 reference statements)

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“…The interaction energies of halogen bonded complexes involving ethers or carbonyl derivatives are linearly correlated to the proton affinities of the base. This is also the case for the present systems.…”

Section: Resultsmentioning

confidence: 99%

Nature of the interaction between ammonia derivatives and carbon disulfide. A theoretical investigation

Zierkiewicz

Michalczyk

Bieńko

et al. 2017

Int J of Quantum Chemistry

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The interactions between NH 3 , its methylated and chlorinated derivatives and CS 2 are investigated by ab initio CCSD(T) and density functional BLYP-D3 methods. The CCSD(T)/aug-cc-pVTZ calculated interaction energies of complexes characterized by the SÁÁÁN chalcogen bonds range between 21.71 and 22.78 kcal mol 21 . The SÁÁÁN bonds are studied by atoms in molecules, natural bond orbital, and noncovalent interaction methods. The lack of correlation between the interaction energies of methylated amines complexes and the electrostatic potential results from the lone pair effect in aliphatic amines. Different structures of CS 2 complexed with ammonia derivatives, stabilized by other than the SÁÁÁN chalcogen bonds, are also predicted. These structures are characterized by interaction energies ranging between 1.15 and 3.46 kcal mol 21 . The results show that the complexing ability of CS 2 is not very high but this molecule is able to attack the electrophilic or nucleophilic sites of a guest molecule. K E Y W O R D S BLYP-D3, CCSD(T), chalcogen bond, lone pair effect, SÁÁÁN bond Int J Quantum Chem. 2017;117:e25369.

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Section: Resultsmentioning

confidence: 99%

Nature of the interaction between ammonia derivatives and carbon disulfide. A theoretical investigation

Zierkiewicz

Michalczyk

Bieńko

et al. 2017

Int J of Quantum Chemistry

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“…In the same way, complex formation between F 3 CCl and various electron donors results in an increase of the positive charge on the Cl atom . The increase of these charges is linearly related to the increase of s‐character of the C(Cl) atom …”

Section: Nbo Analysismentioning

confidence: 89%

Theoretical study of the interaction of fluorinated dimethyl ethers and the ClF and HF molecules. Comparison between halogen and hydrogen bonds

Sutradhar

Chandra

Zeegers‐Huyskens

2016

Int J of Quantum Chemistry

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A theoretical study of the halogen-bonded complexes formed between fluorinated dimethyl ethers (n F 5 0-4) and ClF is carried out using the wB97XD method combined with the 6-31111G(d,p) basis set. The properties of the complexes are compared with the corresponding properties of the hydrogenbonded complexes formed between the same electron donors and HF. The optimized geometries, the interaction energies, relevant natural bonding orbital characteristics along with some vibrational data are calculated. The analyzed properties also include the symmetry adapted perturbation theory decomposition of the energies along with the atoms-in molecule analysis. For both the halogen and hydrogen bonds, the interaction energies are ruled by the intermolecular hyperconjugation energies. In contrast, the correlations between the binding energies and the basic properties of the ethers or the charge transfer are different for the halogen and hydrogen bonds. The applicability of the Bent's rule to these systems is discussed.

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“…To test the applicability of the simplified electrostatic model for describing N−X⋅⋅⋅ − O−N + (X=Br, I) XBs, energies (Δ E model ) obtained from the double regression of the local positive maxima of electrostatic surface potential, V S,max of donor molecules and the local negative maxima of electrostatic surface potential, V S,min of acceptor molecules were correlated with Δ E int values of 32 XB complexes (Figure b) . A reasonably good correlation, R 2 =0.896, was obtained but the data points formed two distinct groups, matching the donor σ‐hole strengths (Supporting Information, Figure S8).…”

Section: Resultsmentioning

confidence: 96%

Strong N−X⋅⋅⋅O−N Halogen Bonds: A Comprehensive Study on N‐Halosaccharin Pyridine N‐Oxide Complexes

2019

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A study of the strong N−X⋅⋅⋅−O−N+ (X=I, Br) halogen bonding interactions reports 2×27 donor×acceptor complexes of N‐halosaccharins and pyridine N‐oxides (PyNO). DFT calculations were used to investigate the X⋅⋅⋅O halogen bond (XB) interaction energies in 54 complexes. A simplified computationally fast electrostatic model was developed for predicting the X⋅⋅⋅O XBs. The XB interaction energies vary from −47.5 to −120.3 kJ mol−1; the strongest N−I⋅⋅⋅−O−N+ XBs approaching those of 3‐center‐4‐electron [N−I−N]+ halogen‐bonded systems (ca. 160 kJ mol−1). 1H NMR association constants (KXB) determined in CDCl3 and [D6]acetone vary from 2.0×100 to >108 m−1 and correlate well with the calculated donor×acceptor complexation enthalpies found between −38.4 and −77.5 kJ mol−1. In X‐ray crystal structures, the N‐iodosaccharin‐PyNO complexes manifest short interaction ratios (RXB) between 0.65–0.67 for the N−I⋅⋅⋅−O−N+ halogen bond.

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On the nature of halogen bonded complexes between carbonyl bases and chlorotrifluoromethane

Cited by 7 publications

References 73 publications

Nature of the interaction between ammonia derivatives and carbon disulfide. A theoretical investigation

Nature of the interaction between ammonia derivatives and carbon disulfide. A theoretical investigation

Theoretical study of the interaction of fluorinated dimethyl ethers and the ClF and HF molecules. Comparison between halogen and hydrogen bonds

Strong N−X⋅⋅⋅O−N Halogen Bonds: A Comprehensive Study on N‐Halosaccharin Pyridine N‐Oxide Complexes

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