Ab initio and DFT studies of the interaction between carbonyl and thiocarbonyl groups: the role of S···O chalcogen bonds

Zierkiewicz, Wiktor; Fanfrlík, Jindřich; Hobza, Pavel; Michalska, Danuta; Zeegers‐Huyskens, Th.

doi:10.1007/s00214-016-1972-z

Cited by 14 publications

(11 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is surprising that despite the fact that the LP(N)→σ*(C=S) charge transfer is sensitive to the substitution, the elongation of the C=S bond remains more or less constant. A possible explanation is that the increase of σ*(C=S) occupation is nearly compensated by a decrease in π*(C=S) occupation [23]. Another explanation is an electrostatic attractive interaction between the C and S atoms [55].…”

Section: A-complexes Of Pyridinesocsmentioning

confidence: 99%

“…These complexes involve the interaction of the XB...YZ type where Y possesses one or more electron pairs. They have been classified into halogen bonds where B is a halogen [5][6][7][8][9][10][11][12][13][14][15], chalcogen bonds where B = O, S, Se [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34], and more recently, tetrel bonds where B = C, Si [35][36][37][38][39][40][41][42]. These bonds are unusual in that they involve a close approach of two electronegative atoms such as Cl, O, C on the one hand, and Y atoms such as N on the other hand.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

et al. 2020

View full text Add to dashboard Cite

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.

show abstract

Section: A-complexes Of Pyridinesocsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The interactions between CS 2 and Cl ‐ , neutral bases (NH 3 , H 2 O, PH 3 , H 2 S) and FH have been investigated. Recently, the interaction between CS 2 and carbonyl derivatives has been studied by theoretical methods . Let us notice that the CS 2 molecule is one of the main pollutants in the atmosphere and from this point of view, its interaction with other molecules is interesting to investigate.…”

Section: Introductionmentioning

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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…For instance, a hydrogen bonding pattern composed of four S···H interactions to a thiocarbonyl group was observed in the crystal structure of thiourea [68]. Based on previous theoretical studies of model complexes [69,70], a single S···H interaction is expected to be rather weak. However, the stabilizing effect of S···H interactions in Fc 2 CS should be strengthened to a certain extent, remembering that a given S atom can be involved in more than one S···H interaction simultaneously.…”

Section: Resultsmentioning

confidence: 99%

Structure of Diferrocenyl Thioketone: From Molecule to Crystal

et al. 2019

View full text Add to dashboard Cite

Ferrocenyl-functionalized thioketones have recently been recognized as useful building blocks for sulfur-containing compounds with potential applications in materials chemistry. This work is devoted to a single representative of such thioketones, namely diferrocenyl thioketone (Fc2CS), whose structure has been determined here for the first time. Both X-ray crystallography and a wide variety of quantum-chemical methods were used to explore the structure of Fc2CS. In addition to the X-ray structure determination, intermolecular interactions occurring in the crystal structure of Fc2CS were examined in detail by quantum-chemical methods. These methods were also an invaluable tool in studying the molecular structure of Fc2CS, from the gas phase to solutions and to its crystal. Intramolecular interactions governing the conformational behavior of an isolated Fc2CS molecule were deduced from quantum-chemical analyses carried out in orbital space and real space. Our experimental and theoretical results indicate that the main structural features of an isolated Fc2CS molecule in its lowest-energy geometry are retained both upon solvation and in the crystal. The tilt of ferrocenyl groups is only slightly affected by crystal packing forces that are dominated by dispersion. Nonetheless, a network of intermolecular interactions, such as H···H, C···H and S···H, was detected in the Fc2CS crystal but each of them is fairly weak.

show abstract

Ab initio and DFT studies of the interaction between carbonyl and thiocarbonyl groups: the role of S···O chalcogen bonds

Abstract: A SAPT decomposition of the interaction energies allows to conclude that the electrostatic energy is the predominant component in the stronger complexes and that the dispersion energy becomes more important in the weaker van der Waals complexes.

Cited by 14 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

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

Structure of Diferrocenyl Thioketone: From Molecule to Crystal

Contact Info

Product

Resources

About