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

Sutradhar, Dipankar; Chandra, Asit K.; Zeegers‐Huyskens, Th.

doi:10.1002/qua.25083

Cited by 17 publications

(23 citation statements)

References 80 publications

(104 reference statements)

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“…The charge on the N atom also decreases when the H atoms of NH 3 are substituted by CH 3 groups, being equal to −0.807 e in NH 2 CH 3 and −0.391 e in N(CH 3 ) 3 . Our calculations are in quantitative agreement with previous calculations carried out at the HF level with a 3‐21G basis set . These calculations have shown that the Mulliken charges and the V s,min values decrease with increasing methyl substitution on NH 3 .…”

Section: Resultssupporting

confidence: 91%

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: Resultssupporting

confidence: 91%

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 an effort to comprehend this behavior, the redshift in the acetylenic C−H stretching frequencies were plotted against other components of the SAPT2 interaction energy, such as induction, dispersion, and exchange repulsion, and the results are presented in Figure A–C. Similar correlations between various energy components for a variety of hydrogen‐bonded systems have been reported in the literature . It can be seen from Figure that the frequency shifts are linearly correlated with induction energy, which is a second‐order electrostatic effect.…”

Section: Resultssupporting

confidence: 65%

“…Similar correlations between various energy componentsfor avariety of hydrogen-bondeds ystems have been reported in the literature. [45][46][47][48][49][50] It can be seen from Figure 7t hat the frequency shifts are linearly correlated with induction energy,w hich is as econd-order electrostatic effect. The linear correlation suggestst hat even second-order electrostatic effects can influence the vibrational frequency shift.…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic and Ab Initio Investigation of C−H⋅⋅⋅N Hydrogen‐Bonded Complexes of Fluorophenylacetylenes: Frequency Shifts and Correlations

et al. 2016

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The C-H⋅⋅⋅N hydrogen-bonded complexes of several fluorophenyacetylenes with ammonia and methylamine were characterized by a redshift in the acetylenic C-H stretching vibration of the phenylacetylene moiety. These redshifts were linearly correlated with the stabilization energies calculated at the CCSD(T)/CBS//MP2-aug-cc-pVDZ level. Analysis of various components of the interaction energy indicated that the observed redshifts were weakly correlated with the electrostatic component. The weaker linear correlation between the frequency shifts and the electrostatic component between two data sets can perhaps be attributed to the marginal differences in the Stark tuning rate and zero-field shifts. The induction and exchange-repulsion components were linearly correlated. However, the dispersion component depends on the nature of the hydrogen-bond acceptor and shows a quantum jump when the hydrogen-bond acceptor is changed from ammonia to methylamine. The observed linear correlation between the redshifts in the C-H stretching frequencies and the total stabilization energies is due to mutual cancellation of deviations from linearity between various components.

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“…SAPT method slightly overestimated the interaction energy compared with MP2 method while the change trend is the same. The interaction energies E int of the complexes are decomposed into four aspects: electrostatic interaction E elst , exchangeenergies E exch , induction energies E ind , and dispersion energies E disp . As shown in Table , all the E elst , E ind , and E disp are attractive while the E exch is repulsive as expected.…”

Section: Resultsmentioning

confidence: 99%

Theoretical study on the interactions of halogen‐bonds and pnicogen‐bonds in phosphine derivatives with Br₂, BrCl, and BrF

Jiao

Liu

Zhao

et al. 2017

Int J of Quantum Chemistry

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The MP2 ab initio quantum chemistry methods were utilized to study the halogen-bond and pnicogen-bond system formed between PH 2 X (X 5 Br, CH 3 , OH, CN, NO 2 , CF 3 ) and BrY (Y 5 Br, Cl, F). Calculated results show that all substituent can form halogen-bond complexes while part substituent can form pnicogen-bond complexes. Traditional, chlorine-shared and ion-pair halogenbonds complexes have been found with the different substituent X and Y. The halogen-bonds are stronger than the related pnicogen-bonds. For halogen-bonds, strongly electronegative substituents which are connected to the Lewis acid can strengthen the bonds and significantly influenced the structures and properties of the compounds. In contrast, the substituents which connected to the Lewis bases can produce opposite effects. The interaction energies of halogen-bonds are 2.56 to 32.06 kcalÁmol 21 ; The strongest halogen-bond was found in the complex of PH 2 OH···BrF. The interaction energies of pnicogen-bonds are in the range 1.20 to 2.28 kcalÁmol 21 ; the strongest pnicogen-bond was found in PH 2 Br···Br 2 complex. The charge transfer of lp(P) Ar*(BrAY), lp(F) Ar*(BrAP), and lp(Br) Ar*(XAP) play important roles in the formation of the halogen-bonds and pnicogen-bonds, which lead to polarization of the monomers. The polarization caused by the halogen-bond is more obvious than that by the pnicogen-bond, resulting in that some halogenbonds having little covalent character. The symmetry adapted perturbation theory (SAPT) energy decomposition analysis showes that the halogen-bond and pnicogen-bond interactions are predominantly electrostatic and dispersion, respectively. K E Y W O R D Sab initio calculation, halogen-bond, interaction energy, pnicogen-bond, symmetry adapted perturbation theory 1 | I N TR ODU C TI ON Noncovalent interactions often play an important role in the stabilization of macromolecular, such as proteins and nucleic acids. Typically, noncovalent interactions include van der Waals forces, electrostatic interactions, hydrophobic interactions, and hydrogen bonds, in which the hydrogen bonding has been extensively investigated partially due to its high importance in systems involving water molecules. There are still some other types of noncovalent bonding, such as halogen bonding and lithium bonding. [1] These interactions have some similarities to the hydrogen bonding, but the details are not very clear and much effort has been put into revealing the nature of these interactions during the past decades. In our previous Int J Quantum Chem. 2017;117:e25443.

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

Cited by 17 publications

References 80 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

Spectroscopic and Ab Initio Investigation of C−H⋅⋅⋅N Hydrogen‐Bonded Complexes of Fluorophenylacetylenes: Frequency Shifts and Correlations

Theoretical study on the interactions of halogen‐bonds and pnicogen‐bonds in phosphine derivatives with Br₂, BrCl, and BrF

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

Cited by 17 publications

References 80 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

Spectroscopic and Ab Initio Investigation of C−H⋅⋅⋅N Hydrogen‐Bonded Complexes of Fluorophenylacetylenes: Frequency Shifts and Correlations

Theoretical study on the interactions of halogen‐bonds and pnicogen‐bonds in phosphine derivatives with Br2, BrCl, and BrF

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Theoretical study on the interactions of halogen‐bonds and pnicogen‐bonds in phosphine derivatives with Br₂, BrCl, and BrF