Topological analysis of electron localisation function: Unlocking the nature of B C chemical bond. Possible existence of multiple bonds B C and B C

Mierzwa, Grzegorz; Gordon, Agnieszka J.; Berski, Sławomir

doi:10.1016/j.poly.2019.05.035

Cited by 9 publications

(4 citation statements)

References 36 publications

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“…The present study is a part of a larger project, comparing properties of the BB, BC [21], BO [22], BN [23] BF, BCl [24], and BCu [25] bonds, investigated by topological analysis of ELF.…”

Section: Introductionmentioning

confidence: 99%

The nature of multiple boron-nitrogen bonds studied using electron localization function (ELF), electron density (AIM), and natural bond orbital (NBO) methods

2020

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Local nature of the boron-nitrogen (BN) bonding with different formal multiplicities (B≡N, B=N, B-N) have been investigated for 25 experimentally established organoboron molecules in both real and the Hilbert space, using topological analysis of electron localization function (ELF), electron density (AIM), and natural bond orbital (NBO) method. Each BN bond has been represented (ELF) by the bonding disynaptic attractor V(B,N), with the basin electron population between 5.72e and 1.83e, confirming possible existence of all the three bond types. A covalent character of bonding can be associated with the dative mechanism due to the V(B,N) bonding basin formed mainly (91-96%) by the N electron density. Similarly, the NBO method shows 2-center natural orbitals, consisting largely of the hybrids from the N atom. The AIM analysis yields the features typical for shared (H (3,−1) (r) < 0) and closed-shell (∇ 2 ρ (3,−1) (r) > 0) interactions. The delocalization indices, describing electron exchanges between B and N quantum atoms, are smaller than 1.5, even for formally very short triple B≡N bonds.

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“…The present study is a part of a larger project, comparing properties of the BB, BC [21], BO [22], BN [23] BF, BCl [24], and BCu [25] bonds, investigated by topological analysis of ELF.…”

Section: Introductionmentioning

confidence: 99%

The nature of multiple boron-nitrogen bonds studied using electron localization function (ELF), electron density (AIM), and natural bond orbital (NBO) methods

2020

Self Cite

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“…In the 5 a/b Mes derivatives the B1−C21, C21−N2 and N2−B2 distances (ca. 1.45, 1.17 and 1.41 Å, respectively) are all within the range of double bonds,[ 33 , 34 ] while the C1−B1 and N1−C1 bond lengths (ca. 1.51 and 1.34 Å, respectively) suggest only a small amount of π backbonding from the electron‐rich boron to the CAAC ligand.…”

Section: Resultsmentioning

confidence: 99%

Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes

Gärtner

Marek

Arrowsmith

et al. 2021

Chemistry A European J

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Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of hitherto unknown linear 2‐aza‐1,4‐diborabutatrienes.

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“…Where EI frag1 , EI frag1 ref , EI frag2 and EI frag2 ref are the energy indices for fragment 1, fragment 1 reference, fragment 2 and fragment 2 reference, respectively [ 51 ]. The thermodynamic properties; Enthalpy and Gibbs free energy of formation of the various complexes were considered in this study.…”

Section: Methodsmentioning

confidence: 99%

Understanding the aqueous chemistry of quinoline and the diazanaphthalenes: insight from DFT study

Enudi

Louis

Edim

et al. 2021

Heliyon

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The inter-fragment interactions at various binding sites and the overall cluster stability of quinolone (QNOL), cinnoline (CNOL), quinazoline (QNAZ), and quinoxaline (QNOX) complexes with H 2 O were studied using the density functional theory (DFT) approach. The adsorption and H-bond binding energies, and the energy decomposition mechanism was considered to determine the relative stabilization status of the studied clusters. Scanning tunneling microscopy (STM), natural bonding orbitals (NBO) and charge decomposition were studied to expose the electronic distribution and interaction between fragments. The feasibility of formations of the various complexes were also studied by considering their thermodynamic properties. Results from adsorption studies confirmed the actual adsorption of H 2 O molecules on the various binding sites studied, with QNOX clusters exhibiting the best adsorptions. Charge decomposition analysis (CDA) revealed significant charge transfer from substrate to H 2 O fragment in most complexes, except in QNOL, CNOL and QNAZ clusters with H 2 O at binding position 4, where much charges are back-donated to substrate. The O-H inter-fragment bonds was discovered to be stronger than counterpart N-H bonds in the complexes, whilst polarity indices confirmed N-H as more polar covalent than O-H bonds. Thermodynamic considerations revealed that the formation process of all studied complexes are endothermic (þve ΔH f ) and non-spontaneous (þve ΔG f ).

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Topological analysis of electron localisation function: Unlocking the nature of B C chemical bond. Possible existence of multiple bonds B C and B C

Cited by 9 publications

References 36 publications

The nature of multiple boron-nitrogen bonds studied using electron localization function (ELF), electron density (AIM), and natural bond orbital (NBO) methods

The nature of multiple boron-nitrogen bonds studied using electron localization function (ELF), electron density (AIM), and natural bond orbital (NBO) methods

Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes

Understanding the aqueous chemistry of quinoline and the diazanaphthalenes: insight from DFT study

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