The influence of carbon hybridization on coupling constants across C X⋯Cl F dihalogen bond: A computational study

Masoodi, Hamid Reza; Bagheri, Sotoodeh

doi:10.1016/j.cplett.2015.08.016

Cited by 6 publications

(3 citation statements)

References 45 publications

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“…[3] It is not only H-bonds that hold together these metastable complexes, as the forgoing represents a more general scenario . [4][5][6][7][8][9][10][11][12]14] An interesting parallel is offered by the dihydrogen bond which occurs between two H atoms: an acidic H atom in the proton donor interacts with an alkaline H atom in the electron donor, as for example in metal hydrides. [7][8][9] The dihydrogen bond has potential for alkane recognition and hexane isomer separation.…”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9] The dihydrogen bond has potential for alkane recognition and hexane isomer separation. [9] An attractive interaction also occurs between two halogen atoms, [10][11][12] due in part to the existence of a region with positive molecular electrostatic potential (MEP) along the extension of the RÀ X bond (X = halogen), commonly termed a σ-hole. [13] Recently, Scheiner [14] proposed a ditetrel bond between neutral tetrel atoms by introducing an alkali metal atom into TMH 3 (T = tetrel), finding bonds that vary in strength up to 10 kcal/mol.…”

Section: Introductionmentioning

confidence: 99%

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Diboron Bonds Between BX₃ (X=H, F, CH₃) and BYZ₂ (Y=H, F; Z=CO, N₂, CNH)

Yang

Scheiner

2021

ChemPhysChem

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The ability of B atoms on two different molecules to engage with one another in a noncovalent diboron bond is studied by ab initio calculations. Due to electron donation from its substituents, the trivalent B atom of BYZ 2 (Z=CO, N 2 , and CNH; Y=H and F) has the ability to in turn donate charge to the B of a BX 3 molecule (X=H, F, and CH 3 ), thus forming a B•••B diboron bond. These bonds are of two different strengths and character. BH(CO) 2 and BH(CNH) 2 , and their fluorosubstituted analogues BF(CO) 2 and BF(CNH) 2 , engage in a typical noncovalent bond with B(CH 3 ) 3 and BF 3 , with interaction energies in the 3-8 kcal/ mol range. Certain other combinations result in a much stronger diboron bond, in the 26-44 kcal/mol range, and with a high degree of covalent character. Bonds of this type occur when BH 3 is added to BH(CO) 2 , BH(CNH) 2 , BH(N 2 ) 2 , and BF(CO) 2 , or in the complexes of BH(N 2 ) 2 with B(CH 3 ) 3 and BF 3 . The weaker noncovalent bonds are held together by roughly equal electrostatic and dispersion components, complemented by smaller polarization energy, while polarization is primarily responsible for the stronger ones.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Diboron Bonds Between BX₃ (X=H, F, CH₃) and BYZ₂ (Y=H, F; Z=CO, N₂, CNH)

Yang

Scheiner

2021

ChemPhysChem

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“…The chemical and physical properties of an organic molecule can be modified by replacing the hydrogen atom with halogens in the aromatic ring (Puttreddy et al, 2018). Halogens which are directly connected to the aromatic ring (Masoodi & Bagheri, 2015) are involved in a variety of noncovalent interactions, e.g. C-HÁ Á ÁX hydrogen bonds (Arunan et al, 2011), XÁ Á ÁX interactions (Saha et al, 2018; Desiraju et al, 2013) and C-XÁ Á Á interactions (Metrangolo et al, 2008;Pang et al, 2013;Adhikari & Roy, 2018;Shukla et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Role of halogen-involved intermolecular interactions and existence of isostructurality in the crystal packing of —CF₃ and halogen (Cl or Br or I) substituted benzamides

Mondal

Shukla

Biswas

et al. 2018

Acta Crystallogr Sect B

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A total of 23 benzamides are obtained through a simple reaction between chloro-/bromo-/iodoaniline and trifluoromethylbenzoyl chloride and characterized using single-crystal X-ray diffraction. Crystal structures of three series of benzamides based on N-chlorophenyl-trifluoromethyl-benzamide (nine compounds), N-bromophenyl-trifluoromethyl-benzamide (six compounds), and N-iodophenyl-trifluoromethyl-benzamide (eight compounds) are prepared to analyse the halogen-mediated noncovalent interactions. The influences of Cl/Br/I and trifluoromethyl substituents on the respective interactions are examined in the presence of a strong N-HÁ Á ÁO hydrogen bond. This exercise has resulted in the documentation of frequently occurring supramolecular synthons involving halogen atoms in the crystal packing of benzamide molecules in the solid state. In the present study, a detailed quantitative evaluation has been performed on the nature, energetics, electrostatic contributions, and topological properties of short and directional intermolecular interactions derived from the electron density on halogenated benzamides in the solid state. Besides these, the occurrence of three-, two-and one-dimensional isostructurality in halogen (Cl or Br or I) substituted benzamide analogues is also investigated. A 'region of co-existence' involving halogen-based intermolecular interactions in the vicinity of the sum of the van der Waals radii has been identified. Thus, the nature of the halogen (effective size), type of interaction and the packing characteristics via presence of additional interactions establish the subtle, yet important, role of cooperativity in intermolecular interactions in crystal packing.

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Stability and electronic properties of binary systems involving hydrogen and halogen bonded [12]cyclacenes: a DFT study

Masoodi

Bagheri

2020

Struct Chem

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The influence of carbon hybridization on coupling constants across C X⋯Cl F dihalogen bond: A computational study

Cited by 6 publications

References 45 publications

Diboron Bonds Between BX₃ (X=H, F, CH₃) and BYZ₂ (Y=H, F; Z=CO, N₂, CNH)

Diboron Bonds Between BX₃ (X=H, F, CH₃) and BYZ₂ (Y=H, F; Z=CO, N₂, CNH)

Role of halogen-involved intermolecular interactions and existence of isostructurality in the crystal packing of —CF₃ and halogen (Cl or Br or I) substituted benzamides

Stability and electronic properties of binary systems involving hydrogen and halogen bonded [12]cyclacenes: a DFT study

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The influence of carbon hybridization on coupling constants across C X⋯Cl F dihalogen bond: A computational study

Cited by 6 publications

References 45 publications

Diboron Bonds Between BX3 (X=H, F, CH3) and BYZ2 (Y=H, F; Z=CO, N2, CNH)

Diboron Bonds Between BX3 (X=H, F, CH3) and BYZ2 (Y=H, F; Z=CO, N2, CNH)

Role of halogen-involved intermolecular interactions and existence of isostructurality in the crystal packing of —CF3 and halogen (Cl or Br or I) substituted benzamides

Stability and electronic properties of binary systems involving hydrogen and halogen bonded [12]cyclacenes: a DFT study

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Diboron Bonds Between BX₃ (X=H, F, CH₃) and BYZ₂ (Y=H, F; Z=CO, N₂, CNH)

Diboron Bonds Between BX₃ (X=H, F, CH₃) and BYZ₂ (Y=H, F; Z=CO, N₂, CNH)

Role of halogen-involved intermolecular interactions and existence of isostructurality in the crystal packing of —CF₃ and halogen (Cl or Br or I) substituted benzamides