Aromaticity in small rings containing boron and carbon, ((CH)2(BH)n, n = 1,2): comarisons with isoelectronic carbocations. The decisive roles of orbital mixing and nonbonded 1,3-interactions in the structures of four-membered rings

Krogh‐Jespersen, Karsten; Cremer, Dieter; Dill, James D.; Pople, John A.; Schleyer, P. R.

doi:10.1021/ja00400a018

Cited by 155 publications

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“…Theoretically these small heterocycles are of special interest. A detailed ab initio study of the structure and the stability of thirty three-membered heterocycles composed of nitrogen, carbon, and oxygen has been published recently [27] and an ab initio study of aromaticity in small ring molecules containing boron and carbon has just been reported [28]. Nevertheless no attention has been given to a three membered partially unsaturated heterocycle composed of boron, nitrogen, and carbon BNCH4 synthesized by Casanova and Schuster [7], for its two cyclic isomers or for the homologous of cyclopropene, unknown up until now.…”

Section: B Odd Numbered Boron-nitrogen Compoundsmentioning

confidence: 99%

Quantum study of the ground state of a series of unsaturated boron–nitrogen compounds by the MNDO method. I. Geometries and stabilities

Maouche

Gayoso

1983

Int J of Quantum Chemistry

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A MNDO study of molecular geometries, enthalpies, formation, atomization, bond separation, and hydrogenation of a series of unsaturated boron-nitrogen compounds, linear with two and three members and cyclic with three, four, five, and six members are presented. For all these molecules, MNDO calculations are in excellent agreement with available ab initio calculations or experimental data. The high rotational barrier in aminoborane HlBNH2, 30.6 kcal/mol, and the length of bond in iminoborane HBNH, 1.1 83 A, imply strong double and triple BN bond character in these two molecules. In the odd membered heterocycles, examination of the molecular geometries and energies of equilibrium states shows that in all cases, the stability of the compounds grows with the number of boron atoms and decreases with that of the nitrogen atoms. Moreover, compared study of the two BN-fulvenes with their homologous hydrocarbon shows that only BN (BB)-fulvene has a polyenic structure similar to that of fulvene.

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Section: B Odd Numbered Boron-nitrogen Compoundsmentioning

confidence: 99%

Quantum study of the ground state of a series of unsaturated boron–nitrogen compounds by the MNDO method. I. Geometries and stabilities

Maouche

Gayoso

1983

Int J of Quantum Chemistry

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“…Before experimental data became available, theoreticians had predicted that the cyclic, 2p-Hückel aromatic compound borirene, (CH) 2 BH, is thermodynamically stable [ Figure 1, (1)]. [7][8][9][10] Efforts have also been made to understand the effect of boronsubstitution and insertion reactions into hydrocarbon molecules. [11][12][13][14][15] For instance, Andrews and co-workers successfully conducted the reactions of boron atoms with acetylene, [16][17][18] ethylene, [19,20] and ethane [20] utilizing the matrix isolation and infrared (IR) spectroscopy coupled with theoretical calculations on the normal modes of the newly formed molecules.…”

Section: Introductionmentioning

confidence: 99%

A Crossed Molecular Beam Study on the Reaction of Boron Atoms with Methylacetylene and Partially Deuterated Methylacetylene

Zhang¹,

Kao²,

Chang³

et al. 2008

ChemPhysChem

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The reactions of ground-state boron atoms, B((2)P(j)), with methylacetylene, CH3CCH(X(1)A(1)), and its [D3]-substituted isotopomer, CD3CCH(X(1)A(1)), are studied under single collision conditions using the crossed molecular beam technique at collision energies of 21.6 and 21.9 kJ mol(-1), respectively. Utilizing the CD3CCH reactant, detailed information on the dynamics is obtained. The reaction followed indirect scattering dynamics and proceeded through at least two reaction channels via atomic deuterium and hydrogen atom elimination pathways leading eventually to two isotopomers, that is, the C(2v) symmetric D2CCCBH(X(1)A(1)) and D2CCCBD(X(1)A(1)) structures via statistical and non-statistical reaction pathways, respectively.

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“…In allen Verbindungen liegt daher Rotationshinderung um die B-N-Bindungen vor. [*] (9), Bl-N1 l.RRY(8). B2-N2 1.386 (6).…”

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1‐Hetero‐3,4‐diborolane und zwei neue Wege zu 1,2‐Diboretanen

Littger¹,

Nöth²,

Thomann³

1993

Angewandte Chemie

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A, /i = 326.90(5) , Z = 4, V = 4599 A'; Vierkreisdiffrdktometer (Mo,,-Strahlung, (o-Scan), 291 3 beobdchtete Reflexe (I > 2q), Nichtwasserstoffatoine anisotrop, H-Atome (bis auf Methylgruppen) in gefundenen Lagen isotrop verfeinert. R = 0.041. Eine Verfeinerung in Cc zeigte starke Korrelation und konvergierte nicht [12]. 112) Weitere Einzelheiten ZLI den Kristdllstrukturuntersuchnngen konnen helm Fachinforniationszentrum Karlsruhe, Gesellschaft fur wissenschaftiichtechnische Information mbH, W-7514 Eggenstein-Leopoldshafen 2, unter Angdbe der Hinterlegungsnuminer CSD-56771, der Autoren uiid des Zeitschriftenzitdts angefordert werdcn.

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Aromaticity in small rings containing boron and carbon, ((CH)2(BH)n, n = 1,2): comarisons with isoelectronic carbocations. The decisive roles of orbital mixing and nonbonded 1,3-interactions in the structures of four-membered rings

Cited by 155 publications

References 0 publications

Quantum study of the ground state of a series of unsaturated boron–nitrogen compounds by the MNDO method. I. Geometries and stabilities

Quantum study of the ground state of a series of unsaturated boron–nitrogen compounds by the MNDO method. I. Geometries and stabilities

A Crossed Molecular Beam Study on the Reaction of Boron Atoms with Methylacetylene and Partially Deuterated Methylacetylene

1‐Hetero‐3,4‐diborolane und zwei neue Wege zu 1,2‐Diboretanen

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