Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-σ and p-π interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes

Mikhail E. Gurskii; Alexei V. Gueiderikh; Yuri N. Bubnov; Mikhail Yu Antipin; Konstantin A. Lyssenko; Ilya D. Gridnev; Roland Boese; Dieter Blaeser

doi:10.1016/S0022-328X(01)00759-8

Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-σ and p-π interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes

Mikhail E. Gurskii, Alexei V. Gueiderikh, Yuri N. Bubnov, Mikhail Yu Antipin, Konstantin A. Lyssenko, Ilya D. Gridnev, Roland Boese, Dieter Blaeser

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

Intramolecular interactions between the unoccupied p-orbital of the boron atom and the σ- (Me) or π-orbital (Ph) of the 7-endo-substituent lead to an unusual stability of the chair-chair conformation in 3-borabicyclo[3.3.1]nonanes. X-ray analysis of 3,7α-dimethyl-3-borabicyclo[3.3.1]nonane (7) and 3-methyl-7α-phenyl-3-borabicyclo[3.3.1]nonane (8), and single point ab initio calculation (B3LYP/6-31G*) of 8 have confirmed the existence of this specific attractive interaction.

Original language	English
Pages (from-to)	3-6
Number of pages	4
Journal	Journal of Organometallic Chemistry
Volume	636
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(01)00759-8
Publication status	Published - 2001 Nov 25
Externally published	Yes

Keywords

3-Borabicyclo[3.3.1]nonanes
Conformation analysis
P-σ and p-π interactions
X-ray analysis

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(01)00759-8

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Gurskii, M. E., Gueiderikh, A. V., Bubnov, Y. N., Antipin, M. Y., Lyssenko, K. A., Gridnev, I. D., Boese, R., & Blaeser, D. (2001). Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-σ and p-π interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes. Journal of Organometallic Chemistry, 636(1-2), 3-6. https://doi.org/10.1016/S0022-328X(01)00759-8

Gurskii, ME, Gueiderikh, AV, Bubnov, YN, Antipin, MY, Lyssenko, KA, Gridnev, ID, Boese, R & Blaeser, D 2001, 'Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-σ and p-π interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes', Journal of Organometallic Chemistry, vol. 636, no. 1-2, pp. 3-6. https://doi.org/10.1016/S0022-328X(01)00759-8

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title = "Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-σ and p-π interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes",

abstract = "Intramolecular interactions between the unoccupied p-orbital of the boron atom and the σ- (Me) or π-orbital (Ph) of the 7-endo-substituent lead to an unusual stability of the chair-chair conformation in 3-borabicyclo[3.3.1]nonanes. X-ray analysis of 3,7α-dimethyl-3-borabicyclo[3.3.1]nonane (7) and 3-methyl-7α-phenyl-3-borabicyclo[3.3.1]nonane (8), and single point ab initio calculation (B3LYP/6-31G*) of 8 have confirmed the existence of this specific attractive interaction.",

keywords = "3-Borabicyclo[3.3.1]nonanes, Conformation analysis, P-σ and p-π interactions, X-ray analysis",

author = "Gurskii, {Mikhail E.} and Gueiderikh, {Alexei V.} and Bubnov, {Yuri N.} and Antipin, {Mikhail Yu} and Lyssenko, {Konstantin A.} and Gridnev, {Ilya D.} and Roland Boese and Dieter Blaeser",

note = "Funding Information: This work was carried out with the financial support of the Russian Foundation for Basic Research (Project Nos. 98-03-32993a, 00-15-97378 and 00-03-32807a). ",

year = "2001",

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day = "25",

doi = "10.1016/S0022-328X(01)00759-8",

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journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

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AU - Gurskii, Mikhail E.

AU - Gueiderikh, Alexei V.

AU - Bubnov, Yuri N.

AU - Antipin, Mikhail Yu

AU - Lyssenko, Konstantin A.

AU - Gridnev, Ilya D.

AU - Boese, Roland

AU - Blaeser, Dieter

N1 - Funding Information: This work was carried out with the financial support of the Russian Foundation for Basic Research (Project Nos. 98-03-32993a, 00-15-97378 and 00-03-32807a).

PY - 2001/11/25

Y1 - 2001/11/25

N2 - Intramolecular interactions between the unoccupied p-orbital of the boron atom and the σ- (Me) or π-orbital (Ph) of the 7-endo-substituent lead to an unusual stability of the chair-chair conformation in 3-borabicyclo[3.3.1]nonanes. X-ray analysis of 3,7α-dimethyl-3-borabicyclo[3.3.1]nonane (7) and 3-methyl-7α-phenyl-3-borabicyclo[3.3.1]nonane (8), and single point ab initio calculation (B3LYP/6-31G*) of 8 have confirmed the existence of this specific attractive interaction.

AB - Intramolecular interactions between the unoccupied p-orbital of the boron atom and the σ- (Me) or π-orbital (Ph) of the 7-endo-substituent lead to an unusual stability of the chair-chair conformation in 3-borabicyclo[3.3.1]nonanes. X-ray analysis of 3,7α-dimethyl-3-borabicyclo[3.3.1]nonane (7) and 3-methyl-7α-phenyl-3-borabicyclo[3.3.1]nonane (8), and single point ab initio calculation (B3LYP/6-31G*) of 8 have confirmed the existence of this specific attractive interaction.

KW - 3-Borabicyclo[3.3.1]nonanes

KW - Conformation analysis

KW - P-σ and p-π interactions

KW - X-ray analysis

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Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-σ and p-π interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes

Abstract

Keywords

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