Hybrid Boron-Carbon Chemistry

Abstract

The recently proved one-to-one structural equivalence between a conjugated hydrocarbon CnHm and the corresponding borane BnHm+n is applied here to hybrid systems, where each C=C double bond in the hydrocarbon is consecutively substituted by planar B(H2)B moieties from diborane(6). Quantum chemical computations with the B3LYP/cc-pVTZ method show that the structural equivalences are maintained along the substitutions, even for non-planar systems. We use as benchmark aromatic and antiaromatic (poly)cyclic conjugated hydrocarbons: cyclobutadiene, benzene, cyclooctatetraene, pentalene, benzocyclobutadiene, naphthalene and azulene. The transformation of these conjugated hydrocarbons to the corresponding boranes is analyzed from the viewpoint of geometry and electronic structure.

A Quantum-Chemical Study of Boro-Fullerenes B₆₀H₆₀, B₆₀F₃₀H₃₀ , and B₆₀F₆₀

“…In an attempt to relate boron and carbon 2D chemistries, a recent experimental finding calls for a potential new 2D boron chemistry: the isolation from the superconductor MgB2 of a borophane 2D layer (BH)1 isostructural and isoelectronic with graphene [46]. Previous theoretical works on the prediction of planarity in boron molecules and boron compounds have been published [1,6,10,11,47]. The simple link between hydrocarbon and borane chemistries [5] can be applied to conjugated hydrocarbons CnHm and the corresponding boranes BnHm+n [10,11].…”

“…Previous theoretical works on the prediction of planarity in boron molecules and boron compounds have been published [1,6,10,11,47]. The simple link between hydrocarbon and borane chemistries [5] can be applied to conjugated hydrocarbons CnHm and the corresponding boranes BnHm+n [10,11]. If we set m = 0, the transformation Cn  BnHn can be established.…”

“…On the other hand, a simple link between hydrocarbon and borohydride (borane) chemistries [5] can be drawn, in particular within conjugated hydrocarbon chemistry [10,11]: CnHm  BnHm+n ; namely, to any planar or non-planar conjugated hydrocarbon CnHm there corresponds an isostructural and isoelectronic borane BnHm+n. This transformation is easily carried out by substituting all C=C double bonds by the B(H2)B central moiety in diborane (6).…”

“…This transformation is easily carried out by substituting all C=C double bonds by the B(H2)B central moiety in diborane (6). Up to date, all transformations of known conjugated hydrocarbons lead to the same structures as compared to the equivalent boranes [10,11]. However, with the exception of the ethylene  diborane (6) and the 2D graphene  2D (BH)1 borophane sheet correspondences, most of these planar boranes do not exist or have not yet been isolated.…”

Celebrating Todd Marder: 65th Birthday and His Contributions to Inorganic Chemistry

“…Professor Todd B. Marder has contributed significantly to expand the scope of boron chemistry, and it is an honor to celebrate his achievements, and mark his 65th birthday with a Special Issue of Molecules : “Boron in Catalysis and Materials Chemistry: A Themed Issue in Honor of Professor Todd B. Marder on the Occasion of His 65th Birthday”. It includes excellent review articles on conjugated N^C-organoboron materials, and tri(boryl)-alkanes and -alkenes as versatile reagents in organic synthesis [ 31 , 32 ], and research articles depicting diversity [ 33 , 34 , 35 , 36 , 37 , 38 , 39 ], as noted in the research interests of Professor Marder. We thank all the authors for joining us to congratulate Todd, and for making this issue a successful one through their excellent scientific contributions.…”