B=N Bonds and BCN Rings - Reactivity and Charge Density Studies
(F5C6)2BNMe2 (1) was prepared and (F3C)2BNMe2 (2) was resynthesized. The crystal structures of both compounds were determined. In contrast to 2, compound 1 does not react with diazomethanes under carbine insertion into the BN bond. In this way the known (F3C)2BCH(SiMe3)NMe2 (3) was resynthesized fro...
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| Published in | Zeitschrift für anorganische und allgemeine Chemie (1950) Vol. 639; no. 11; pp. 2086 - 2095 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English German |
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Weinheim
WILEY-VCH Verlag
01.09.2013
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
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| Abstract | (F5C6)2BNMe2 (1) was prepared and (F3C)2BNMe2 (2) was resynthesized. The crystal structures of both compounds were determined. In contrast to 2, compound 1 does not react with diazomethanes under carbine insertion into the BN bond. In this way the known (F3C)2BCH(SiMe3)NMe2 (3) was resynthesized from 2 and its solid‐state structure was determined. The electron densities of compounds 1, 2, and 3 and those of the simpler model compound (F3C)2BCH2NMe2 (4) as well as that of the BN/CC isoelectronic compound (F3C)2CCH2CMe2 (5) for comparison were calculated and their topologies analysed in terms of the Quantum Theory of Atoms in Molecules (QTAIM). Despite 2 has a shorter B–N bond in calculations and in the crystal than 1, the atomic charges and electron density parameters to QTAIM are very similar for both compounds and cannot explain the different reactivity. The three‐membered rings 3 and 4 do not show bond‐critical points for their B–N bonds. The nature of the B–N bond region was also analysed in terms of the source function contributions in QTAIM, which demonstrated the importance of the close proximity of a third atom in three‐membered rings for the charge density topologies in such systems. |
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| AbstractList | (F5C6)2BNMe2 (1) was prepared and (F3C)2BNMe2 (2) was resynthesized. The crystal structures of both compounds were determined. In contrast to 2, compound 1 does not react with diazomethanes under carbine insertion into the BN bond. In this way the known (F3C)2BCH(SiMe3)NMe2 (3) was resynthesized from 2 and its solid‐state structure was determined. The electron densities of compounds 1, 2, and 3 and those of the simpler model compound (F3C)2BCH2NMe2 (4) as well as that of the BN/CC isoelectronic compound (F3C)2CCH2CMe2 (5) for comparison were calculated and their topologies analysed in terms of the Quantum Theory of Atoms in Molecules (QTAIM). Despite 2 has a shorter B–N bond in calculations and in the crystal than 1, the atomic charges and electron density parameters to QTAIM are very similar for both compounds and cannot explain the different reactivity. The three‐membered rings 3 and 4 do not show bond‐critical points for their B–N bonds. The nature of the B–N bond region was also analysed in terms of the source function contributions in QTAIM, which demonstrated the importance of the close proximity of a third atom in three‐membered rings for the charge density topologies in such systems. (F5C6)2BNMe2 (1) was prepared and (F3C)2BNMe2 (2) was resynthesized. The crystal structures of both compounds were determined. In contrast to 2, compound 1 does not react with diazomethanes under carbine insertion into the BN bond. In this way the known (F3C)2BCH(SiMe3)NMe2 (3) was resynthesized from 2 and its solid-state structure was determined. The electron densities of compounds 1, 2, and 3 and those of the simpler model compound (F3C)2BCH2NMe2 (4) as well as that of the BN/CC isoelectronic compound (F3C)2CCH2CMe2 (5) for comparison were calculated and their topologies analysed in terms of the Quantum Theory of Atoms in Molecules (QTAIM). Despite 2 has a shorter B-N bond in calculations and in the crystal than 1, the atomic charges and electron density parameters to QTAIM are very similar for both compounds and cannot explain the different reactivity. The three-membered rings 3 and 4 do not show bond-critical points for their B-N bonds. The nature of the B-N bond region was also analysed in terms of the source function contributions in QTAIM, which demonstrated the importance of the close proximity of a third atom in three-membered rings for the charge density topologies in such systems. [PUBLICATION ABSTRACT] Abstract (F 5 C 6 ) 2 BNMe 2 ( 1 ) was prepared and (F 3 C) 2 BNMe 2 ( 2 ) was resynthesized. The crystal structures of both compounds were determined. In contrast to 2 , compound 1 does not react with diazomethanes under carbine insertion into the BN bond. In this way the known (F 3 C) 2 BCH(SiMe 3 )NMe 2 ( 3 ) was resynthesized from 2 and its solid‐state structure was determined. The electron densities of compounds 1 , 2 , and 3 and those of the simpler model compound (F 3 C) 2 BCH 2 NMe 2 ( 4 ) as well as that of the BN/CC isoelectronic compound (F 3 C) 2 CCH 2 CMe 2 ( 5 ) for comparison were calculated and their topologies analysed in terms of the Quantum Theory of Atoms in Molecules (QTAIM). Despite 2 has a shorter B–N bond in calculations and in the crystal than 1 , the atomic charges and electron density parameters to QTAIM are very similar for both compounds and cannot explain the different reactivity. The three‐membered rings 3 and 4 do not show bond‐critical points for their B–N bonds. The nature of the B–N bond region was also analysed in terms of the source function contributions in QTAIM, which demonstrated the importance of the close proximity of a third atom in three‐membered rings for the charge density topologies in such systems. |
| Author | Neumann, Beate Mitzel, Norbert W. Winkelhaus, Daniel Berger, Raphael J. F. Stammler, Hans-Georg Vishnevskiy, Yuri V. |
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| Notes | In Memoriam Richard F. W. Bader Deutsche Forschungsgemeinschaft Fonds der Chemischen Industrie istex:C583F191E4D71BCF246EAAC32DD6503BBB9EA6B4 Supporting Information for this article is available on the WWW under http://dx.doi.org/10.1002/zaac.201200483 or from the author. ark:/67375/WNG-SQD0GKT0-Z ArticleID:ZAAC201200483 or from the author. http://dx.doi.org/10.1002/zaac.201200483 Supporting Information for this article is available on the WWW under |
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| Snippet | (F5C6)2BNMe2 (1) was prepared and (F3C)2BNMe2 (2) was resynthesized. The crystal structures of both compounds were determined. In contrast to 2, compound 1... Abstract (F 5 C 6 ) 2 BNMe 2 ( 1 ) was prepared and (F 3 C) 2 BNMe 2 ( 2 ) was resynthesized. The crystal structures of both compounds were determined. In... |
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| SubjectTerms | Boron Chemical bonding Electron density Nitrogen Three-membered rings |
| Title | B=N Bonds and BCN Rings - Reactivity and Charge Density Studies |
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