A theoretical investigation of the interaction between substituted pyridines and CS2. Versatility of the CS2 molecule

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

doi:10.1016/j.molstruc.2019.127309

Cited by 5 publications

(18 citation statements)

References 59 publications

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“…As illustrated in Figure 2, the structures of the A, B, and C complexes are very different and therefore their characteristics will be discussed in different sections. Let us notice that these structures are very similar to those reported for the same pyridine derivatives complexed with CS 2 [46].…”

Section: Binding Energiessupporting

confidence: 82%

“…A positive electrostatic potential belt around the C atom is predicted with a V s,max value of 86.1 kJ/mol. The V s,max values of the S and C atom of OCS are much greater than that for the S-atom (70.9 kJ/mol) and of the C atom (23.1 kJ/mol) of CS 2 molecule [46] because of the presence of O atom in OCS. Interestingly, the S atom develops a belt of negative electrostatic potential with a V s,min value of −6.3 kJ/mol.…”

Section: Pyridinesmentioning

confidence: 78%

“…The values of the molecular electrostatic potentials of the substituted pyridines and OCS which are relevant for the discussion of the results are listed in Table 1. As outlined in a recent work [46], the negative electrostatic potential at the N-atom of substituted pyridines is very sensitive to the substituents, decreasing in the order NH 2 > CH 3 > H > F > CN > NO 2 which is also the order of the p.Hammett constants (−0.660, −0.170, 0.062, 0.660, 0.778) [51]. Table 1.…”

Section: Electrostatic Potential Of the Componentsmentioning

confidence: 96%

“…The structures of A, B, and C complexes of pyridine.OCS are illustrated in Figure 2 where the intermolecular distances are indicated for the unsubstituted pyridine.OCS complex. These structures are the most stable ones and are very similar to those recently predicted for the pyridines.CS 2 complexes [46]. Table 2 reports the binding energies calculated at the MP2=full/aug-cc-pVTZ//aug-cc-pVDZ level.…”

Section: Binding Energiesmentioning

confidence: 99%

“…In a recent work [46], where the interaction between para-substituted pyridine derivatives and CS 2 was investigated, the versatility of the CS 2 molecule which forms with pyridines four types of complexes with different structure was demonstrated. This present work deals with the interaction of para-substituted pyridines with OCS.…”

Section: Introductionmentioning

confidence: 99%

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Nature of the Interaction of Pyridines with OCS. A Theoretical Investigation

et al. 2020

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Ab initio calculations were carried out to investigate the interaction between para-substituted pyridines (X-C5H4N, X=NH2, CH3, H, CN, NO2) and OCS. Three stable structures of pyridine.OCS complexes were detected at the MP2=full/aug-cc-pVDZ level. The A structure is characterized by N…S chalcogen bonds and has binding energies between −9.58 and −12.24 kJ/mol. The B structure is bonded by N…C tetrel bond and has binding energies between −10.78 and −11.81 kJ/mol. The C structure is characterized by π-interaction and has binding energies between −10.76 and −13.33 kJ/mol. The properties of the systems were analyzed by AIM, NBO, and SAPT calculations. The role of the electrostatic potential of the pyridines on the properties of the systems is outlined. The frequency shift of relevant vibrational modes is analyzed.

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Section: Binding Energiessupporting

confidence: 82%

Section: Pyridinesmentioning

confidence: 78%

Section: Electrostatic Potential Of the Componentsmentioning

confidence: 96%

Section: Binding Energiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Nature of the Interaction of Pyridines with OCS. A Theoretical Investigation

et al. 2020

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Strongly Bound π‐Hole Tetrel Bonded Complexes between H₂SiO and Substituted Pyridines. Influence of Substituents

2022

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Ab initio calculation at the MP2/aug-cc-pVTZ level has been performed on the π-hole based N … Si tetrel bonded complexes between substituted pyridines and H 2 SiO. The primary aim of the study is to find out the effect of substitution on the strength and nature of this tetrel bond, and its similarity/difference with the N … C tetrel bond. Correlation between the strength of the N … Si bond and several molecular properties of the Lewis acid (H 2 SiO) and base (pyridines) are explored. The properties of the tetrel bond are analyzed using AIM, NBO, and symmetry-adapted perturbation theory calculations. The complexes are characterized with short N … Si intermolecular distances and high binding energies ranging between À 142.72 and À 115.37 kJ/ mol. The high value of deformation energy indicates significant geometrical distortion of the monomer units. The AIM and NBO analysis reveal significant coordinate covalent bond character of the N•••Si π-hole bond. Sharp differences are also noticed in the orbital interactions present in the N•••Si and N•••C tetrel bonds.

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Nature and Strength of the π‐Hole Chalcogen Bonded Complexes between Substituted Pyridines and SO₃ Molecule

et al. 2021

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A theoretical study has been carried out on the π‐hole based chalcogen bonding interaction between SO3 and various pyridines (XC5H4N), at the MP2=full/aug‐cc‐pVTZ level, to obtain a better insight into the nature and strength of N…S bond. Our calculations predict two different types of chalcogen bonded complexes: (1) Type‐A complex is formed via lone pair‐ π‐hole (N…S) interaction, and (2) Type‐B complex is stabilized through π‐hole‐π‐electron interaction. The binding energy of the Type‐A complexes varies between −109.78 and ‐81.56 kJ/mol whereas it ranges between −28.93 and −17.82 kJ/mol for Type‐B complexes. The nature of the N…S bond and the changes in its properties on the influence of electron donating and electron withdrawing substituents have been discussed with the help of various computational tools like AIM, NCI, SAPT and NBO analysis. The binding energy of the Type‐A complexes are found to correlate with the basicity parameters such as PA and Vs,min of the substituted pyridines. The binding energies of the pyridine complexes with SF2, SO2, CS2 and OCS are also computed for finding the effect of variation of Vs,max value of the S‐atom on the binding energy. The 2nd order hyperconjugation interaction energy between LP(N) and σ*(S−O)/LP*(S) is well correlated to the binding energy as: −ΔE=0.11E(2) −20.08. The variation in the bond distances and their corresponding vibrational frequencies of both the interacting partners (XC5H4N and SO3) are discussed in detail.

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A theoretical investigation of the interaction between substituted pyridines and CS2. Versatility of the CS2 molecule

Cited by 5 publications

References 59 publications

Nature of the Interaction of Pyridines with OCS. A Theoretical Investigation

Nature of the Interaction of Pyridines with OCS. A Theoretical Investigation

Strongly Bound π‐Hole Tetrel Bonded Complexes between H₂SiO and Substituted Pyridines. Influence of Substituents

Nature and Strength of the π‐Hole Chalcogen Bonded Complexes between Substituted Pyridines and SO₃ Molecule

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A theoretical investigation of the interaction between substituted pyridines and CS2. Versatility of the CS2 molecule

Cited by 5 publications

References 59 publications

Nature of the Interaction of Pyridines with OCS. A Theoretical Investigation

Nature of the Interaction of Pyridines with OCS. A Theoretical Investigation

Strongly Bound π‐Hole Tetrel Bonded Complexes between H2SiO and Substituted Pyridines. Influence of Substituents

Nature and Strength of the π‐Hole Chalcogen Bonded Complexes between Substituted Pyridines and SO3 Molecule

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Product

Resources

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Strongly Bound π‐Hole Tetrel Bonded Complexes between H₂SiO and Substituted Pyridines. Influence of Substituents

Nature and Strength of the π‐Hole Chalcogen Bonded Complexes between Substituted Pyridines and SO₃ Molecule