Theoretical study of noncovalent interactions between triple bonds and chlorine atoms in complexes of acetylene and some chloromethanes

Tomura, Masaaki

doi:10.1016/j.chemphys.2009.03.015

Cited by 10 publications

(8 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It should be noted that in isolated complexes of halomethanes with acetylene, the C-halogen bond is oriented exactly toward the center of the triple bond. 35 However, other intermolecular interactions acting in several directions induce deformations of the ideal geometry, and in the complexes under consideration, the Cl atom is always closer to one of the C sp carbon atoms than to the center of triple bond. A similar situation was also found in the case of halogen bonds to a benzene ring.…”

Section: Hm6p:dcm Host-guest Interactionsmentioning

confidence: 99%

See 1 more Smart Citation

The C–Cl⋯π interactions inside supramolecular nanotubes of hexaethynylhexamethoxy[6]pericyclyne

Шишкин

Zubatyuk

Dyakonenko

et al. 2011

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

Model complexes of hexaethynylhexamethoxy[6]pericyclyne (HM6P) molecules, with or without dichloromethane (DCM) guests, have been calculated at the M05-2X/6-311G(d,p) DFT level. Analysis of nonbonding interactions shows that the cohesion of the supramolecular tubular assemblies previously observed in the crystal state, relies mainly on C-H···O hydrogen bonds between axial ethynyl and equatorial methoxy substituents of stacked HM6P C(18) macrocycles in a cyclohexane-like chair conformation. The intrinsic binding energy of one HM6P molecule with two neighbors is calculated to be more than 40 kcal mol(-1). The inner channel of the stacks (of ca. 8 Å diameter) are suitable for hosting DCM molecules. Using the Atoms In Molecules (AIM) theory, the interaction between DCM molecules and surrounding triple bonds is analyzed in terms of σ-hole-directed C-Cl···π halogen bonds. A σ-hole-directed Cl···Cl interaction between two chlorine atoms of different DCM molecules is also evidenced.

show abstract

Section: Hm6p:dcm Host-guest Interactionsmentioning

confidence: 99%

“…[26][27][28] Such interactions were found in many crystals. 9,29,30 Formation of s-hole bonds is also observed between halogen atoms and conjugatively isolated double 31 and triple [32][33][34][35] bonds. However, the interactions of halogen atoms with p-systems are more complicated than with heteroatomic lone pairs.…”

Section: Introductionmentioning

confidence: 96%

The C–Cl⋯π interactions inside supramolecular nanotubes of hexaethynylhexamethoxy[6]pericyclyne

Шишкин

Zubatyuk

Dyakonenko

et al. 2011

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

show abstract

“…Structure 3 is stabilized by so-called halogen bonding, which has been recently predicted and discussed by Tomura. 44 All these structures are the real minima on the PES. Besides structure 4 which corresponds to the global minimum, the calculations predict only a slightly smaller (B0.5 kJ mol À1 ) absolute value of DE e for the so called T-shaped structure.…”

Section: Results Of Measurementsmentioning

confidence: 95%

Strong and weak effects caused by non covalent interactions between chloroform and selected electron donor molecules

Rutkowski

Меликова

Роспенк

et al. 2011

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

The FTIR spectra of chloroform (Cl(3)CH) in mixtures with various electron donors (B = CH(3)CCH, HCCH, NCCD(3), ClCD(3) and CO) have been studied in liquefied Kr. Spectroscopic evidence of weak H-bond formation has been found. The relative stability of some complexes has been evaluated from temperature studies of integrated intensities of vibrational bands attributed to monomer and complex species. A weak red shift of the stretching vibration of chloroform involved in H-bonding with CH(3)CCH and HCCH having π-electron area was observed. However, in the case of interactions with NCCD(3) and CO, a weak blue shift was detected. In most of the cases, a noticeable increase in the integrated intensity of the CH stretching band was found. Ab initio MP2/6-311++G(2d,2p) a priori counterpoise corrected calculations have been performed for a series of Cl(3)CH and B. Stationary points at the potential energy surface were examined and the structures related to the real minima have been found. The calculations reproduce the majority of experimental results. It has been found that the commonly used correlation between the frequency shift of the CH stretching vibration of the proton donor subunit and the change in CH bond length can fail in the case of the complexes characterized by a weak frequency shift effect.

show abstract

“…Halogen bonding (XB) in recent time has gathered a tremendous amount of attention because of its importance in liquid crystals, polymerization, crystal engineering, and biomedical applications . Besides, in the atoms having a lone pair of electrons such as O, N, and S, the halogen acceptor in XBs include π systems, metal hydrides, radicals, and carbenes . Halogen bonding can generally be depicted as RX···B interactions, where X represents an halogen atom, R can be an halogen atom or an organic or inorganic residue, and B is a Lewis base .…”

Section: Introductionmentioning

confidence: 99%

“…[4] Besides, in the atoms having a lone pair of electrons such as O, N, and S, the halogen acceptor in XBs include p systems, metal hydrides, radicals, and carbenes. [5][6][7][8][9] Halogen bonding can generally be depicted as RAXÁÁÁB interactions, where X represents an halogen atom, R can be an halogen atom or an organic or inorganic residue, and B is a Lewis base. [10] This bonding has been discussed in several recent works.…”

mentioning

confidence: 99%

Halogen bonding between substituted chlorobenzene and trimethylamine: Decisive role of σ–hole and CCl bond breaking energy

Sutradhar

Chandra

2017

Int J of Quantum Chemistry

View full text Add to dashboard Cite

Theoretical studies have been carried out on the halogen bonding interaction between para substituted chlorobenzene (YC6H4Cl, Y = H, NH2, CH3, F, CN, NO2) and N(CH3)3 using ab initio MP2/aug‐cc‐pVDZ and DFT based wB97XD/6‐311++G(d,p) methods. The positive electrostatic potential (VS,max) on the Cl atom and the heterolytic bond breaking enthalpy of the CCl bond have been calculated and their role on halogen bonding is discussed. The heterolytic bond breaking enthalpy of the CCl bond is proposed as a measure of the strength of the σ‐hole on Cl atom. The binding strength of the complexes ranging between −6.13 kJ mol−1 and −9.29 kJ mol−1 are linearly related to the VS,max of the Cl atom and the bond breaking enthalpy of the CCl bond. In addition, energy decomposition analysis was performed on the halogen bonded complexes via symmetry adapted perturbation theory (SAPT) to predict the dominant energy component and the nature of the N···Cl interaction.

show abstract

Theoretical study of noncovalent interactions between triple bonds and chlorine atoms in complexes of acetylene and some chloromethanes

Cited by 10 publications

References 47 publications

The C–Cl⋯π interactions inside supramolecular nanotubes of hexaethynylhexamethoxy[6]pericyclyne

The C–Cl⋯π interactions inside supramolecular nanotubes of hexaethynylhexamethoxy[6]pericyclyne

Strong and weak effects caused by non covalent interactions between chloroform and selected electron donor molecules

Halogen bonding between substituted chlorobenzene and trimethylamine: Decisive role of σ–hole and CCl bond breaking energy

Contact Info

Product

Resources

About