Evaluation of dispersion type metal (...) pi arene interaction in arylbismuth compounds - an experimental and theoretical study

Ana-Maria Preda, Malgorzata Krasowska, Lydia Wrobel, Philipp Kitschke, Phil C. Andrews, Jonathan G. MacLellan, Lutz Mertens, Marcus Korb, Tobias Rueffer, Heinrich Lang, Alexander A. Auer, Michael Mehring

Research output: Contribution to journalArticle

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Abstract

The dispersion type Bi (...) pi arene interaction is one of the important structural features in the assembly process of arylbismuth compounds. Several triarylbismuth compounds and polymorphs are discussed and compared based on the analysis of single crystal X-ray diffraction data and computational studies. First, the crystal structures of polymorphs of Ph3Bi (1) are described emphasizing on the description of London dispersion type bismuth (...) pi arene interactions and other van der Waals interactions in the solid state and the effect of it on polymorphism. For comparison we have chosen the substituted arylbismuth compounds (C6H4-CH = CH2-4)(3)Bi (2), (C6H4-OMe-4)(3)Bi (3), (C6H3-t-Bu2-3,5)(3)Bi (4) and (C6H3-t-Bu-2-3,5)(2)BiCl (5). The structural analyses revealed that only two of them show London dispersion type bismuth ... pi arene interactions. One of them is the styryl derivative 2, for which two polymorphs were isolated. Polymorph 2a crystallizes in the orthorhombic space group P2(1)2(1)2(1), while polymorph 2b exhibits the monoclinic space group P2(1/c). The general structure of 2a is similar to the monoclinic C2/c modification of Ph3Bi (1a), which leads to the formation of zig-zag Bi-arene(centroid) ribbons formed as a result of bismuth (...) pi arene interactions and pi (...) pi intermolecular contacts. In the crystal structures of the polymorph 2b as well as for 4 bismuth (...) pi arene interactions are not observed, but both compounds revealed C-HPh (...) pi intermolecular contacts, as likewise observed in all of the three described polymorphs of Ph3Bi. For compound 3 intermolecular contacts as a result of coordination of the methoxy group to neighboring bismuth atoms are observed overruling Bi (...) pi arene contacts. Compound 5 shows a combination of donor acceptor Bi (...) Cl and Bi (...) pi arene interactions, resulting in an intermolecular pincer-type coordination at the bismuth atom. A detailed analysis of three polymorphs of Ph3Bi (1), which were chosen as model systems, at the DFT-D level of theory supported by DLPNO-CCSD(T) calculations reveals how van der Waals interactions between different structural features balance in order to stabilize molecular arrangements present in the crystal structure. Furthermore, the computational results allow to group this class of compounds into the range of heavy main group element compounds which have been characterized as dispersion energy donors in previous work.

Original languageEnglish
Pages (from-to)2125-2145
Number of pages21
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
Publication statusPublished - 15 Aug 2018
Externally publishedYes

Cite this

Preda, Ana-Maria ; Krasowska, Malgorzata ; Wrobel, Lydia ; Kitschke, Philipp ; Andrews, Phil C. ; MacLellan, Jonathan G. ; Mertens, Lutz ; Korb, Marcus ; Rueffer, Tobias ; Lang, Heinrich ; Auer, Alexander A. ; Mehring, Michael. / Evaluation of dispersion type metal (...) pi arene interaction in arylbismuth compounds - an experimental and theoretical study. In: Beilstein Journal of Organic Chemistry. 2018 ; Vol. 14. pp. 2125-2145.
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abstract = "The dispersion type Bi (...) pi arene interaction is one of the important structural features in the assembly process of arylbismuth compounds. Several triarylbismuth compounds and polymorphs are discussed and compared based on the analysis of single crystal X-ray diffraction data and computational studies. First, the crystal structures of polymorphs of Ph3Bi (1) are described emphasizing on the description of London dispersion type bismuth (...) pi arene interactions and other van der Waals interactions in the solid state and the effect of it on polymorphism. For comparison we have chosen the substituted arylbismuth compounds (C6H4-CH = CH2-4)(3)Bi (2), (C6H4-OMe-4)(3)Bi (3), (C6H3-t-Bu2-3,5)(3)Bi (4) and (C6H3-t-Bu-2-3,5)(2)BiCl (5). The structural analyses revealed that only two of them show London dispersion type bismuth ... pi arene interactions. One of them is the styryl derivative 2, for which two polymorphs were isolated. Polymorph 2a crystallizes in the orthorhombic space group P2(1)2(1)2(1), while polymorph 2b exhibits the monoclinic space group P2(1/c). The general structure of 2a is similar to the monoclinic C2/c modification of Ph3Bi (1a), which leads to the formation of zig-zag Bi-arene(centroid) ribbons formed as a result of bismuth (...) pi arene interactions and pi (...) pi intermolecular contacts. In the crystal structures of the polymorph 2b as well as for 4 bismuth (...) pi arene interactions are not observed, but both compounds revealed C-HPh (...) pi intermolecular contacts, as likewise observed in all of the three described polymorphs of Ph3Bi. For compound 3 intermolecular contacts as a result of coordination of the methoxy group to neighboring bismuth atoms are observed overruling Bi (...) pi arene contacts. Compound 5 shows a combination of donor acceptor Bi (...) Cl and Bi (...) pi arene interactions, resulting in an intermolecular pincer-type coordination at the bismuth atom. A detailed analysis of three polymorphs of Ph3Bi (1), which were chosen as model systems, at the DFT-D level of theory supported by DLPNO-CCSD(T) calculations reveals how van der Waals interactions between different structural features balance in order to stabilize molecular arrangements present in the crystal structure. Furthermore, the computational results allow to group this class of compounds into the range of heavy main group element compounds which have been characterized as dispersion energy donors in previous work.",
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author = "Ana-Maria Preda and Malgorzata Krasowska and Lydia Wrobel and Philipp Kitschke and Andrews, {Phil C.} and MacLellan, {Jonathan G.} and Lutz Mertens and Marcus Korb and Tobias Rueffer and Heinrich Lang and Auer, {Alexander A.} and Michael Mehring",
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Preda, A-M, Krasowska, M, Wrobel, L, Kitschke, P, Andrews, PC, MacLellan, JG, Mertens, L, Korb, M, Rueffer, T, Lang, H, Auer, AA & Mehring, M 2018, 'Evaluation of dispersion type metal (...) pi arene interaction in arylbismuth compounds - an experimental and theoretical study' Beilstein Journal of Organic Chemistry, vol. 14, pp. 2125-2145. https://doi.org/10.3762/bjoc.14.187

Evaluation of dispersion type metal (...) pi arene interaction in arylbismuth compounds - an experimental and theoretical study. / Preda, Ana-Maria; Krasowska, Malgorzata; Wrobel, Lydia; Kitschke, Philipp; Andrews, Phil C.; MacLellan, Jonathan G.; Mertens, Lutz; Korb, Marcus; Rueffer, Tobias; Lang, Heinrich; Auer, Alexander A.; Mehring, Michael.

In: Beilstein Journal of Organic Chemistry, Vol. 14, 15.08.2018, p. 2125-2145.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Evaluation of dispersion type metal (...) pi arene interaction in arylbismuth compounds - an experimental and theoretical study

AU - Preda, Ana-Maria

AU - Krasowska, Malgorzata

AU - Wrobel, Lydia

AU - Kitschke, Philipp

AU - Andrews, Phil C.

AU - MacLellan, Jonathan G.

AU - Mertens, Lutz

AU - Korb, Marcus

AU - Rueffer, Tobias

AU - Lang, Heinrich

AU - Auer, Alexander A.

AU - Mehring, Michael

PY - 2018/8/15

Y1 - 2018/8/15

N2 - The dispersion type Bi (...) pi arene interaction is one of the important structural features in the assembly process of arylbismuth compounds. Several triarylbismuth compounds and polymorphs are discussed and compared based on the analysis of single crystal X-ray diffraction data and computational studies. First, the crystal structures of polymorphs of Ph3Bi (1) are described emphasizing on the description of London dispersion type bismuth (...) pi arene interactions and other van der Waals interactions in the solid state and the effect of it on polymorphism. For comparison we have chosen the substituted arylbismuth compounds (C6H4-CH = CH2-4)(3)Bi (2), (C6H4-OMe-4)(3)Bi (3), (C6H3-t-Bu2-3,5)(3)Bi (4) and (C6H3-t-Bu-2-3,5)(2)BiCl (5). The structural analyses revealed that only two of them show London dispersion type bismuth ... pi arene interactions. One of them is the styryl derivative 2, for which two polymorphs were isolated. Polymorph 2a crystallizes in the orthorhombic space group P2(1)2(1)2(1), while polymorph 2b exhibits the monoclinic space group P2(1/c). The general structure of 2a is similar to the monoclinic C2/c modification of Ph3Bi (1a), which leads to the formation of zig-zag Bi-arene(centroid) ribbons formed as a result of bismuth (...) pi arene interactions and pi (...) pi intermolecular contacts. In the crystal structures of the polymorph 2b as well as for 4 bismuth (...) pi arene interactions are not observed, but both compounds revealed C-HPh (...) pi intermolecular contacts, as likewise observed in all of the three described polymorphs of Ph3Bi. For compound 3 intermolecular contacts as a result of coordination of the methoxy group to neighboring bismuth atoms are observed overruling Bi (...) pi arene contacts. Compound 5 shows a combination of donor acceptor Bi (...) Cl and Bi (...) pi arene interactions, resulting in an intermolecular pincer-type coordination at the bismuth atom. A detailed analysis of three polymorphs of Ph3Bi (1), which were chosen as model systems, at the DFT-D level of theory supported by DLPNO-CCSD(T) calculations reveals how van der Waals interactions between different structural features balance in order to stabilize molecular arrangements present in the crystal structure. Furthermore, the computational results allow to group this class of compounds into the range of heavy main group element compounds which have been characterized as dispersion energy donors in previous work.

AB - The dispersion type Bi (...) pi arene interaction is one of the important structural features in the assembly process of arylbismuth compounds. Several triarylbismuth compounds and polymorphs are discussed and compared based on the analysis of single crystal X-ray diffraction data and computational studies. First, the crystal structures of polymorphs of Ph3Bi (1) are described emphasizing on the description of London dispersion type bismuth (...) pi arene interactions and other van der Waals interactions in the solid state and the effect of it on polymorphism. For comparison we have chosen the substituted arylbismuth compounds (C6H4-CH = CH2-4)(3)Bi (2), (C6H4-OMe-4)(3)Bi (3), (C6H3-t-Bu2-3,5)(3)Bi (4) and (C6H3-t-Bu-2-3,5)(2)BiCl (5). The structural analyses revealed that only two of them show London dispersion type bismuth ... pi arene interactions. One of them is the styryl derivative 2, for which two polymorphs were isolated. Polymorph 2a crystallizes in the orthorhombic space group P2(1)2(1)2(1), while polymorph 2b exhibits the monoclinic space group P2(1/c). The general structure of 2a is similar to the monoclinic C2/c modification of Ph3Bi (1a), which leads to the formation of zig-zag Bi-arene(centroid) ribbons formed as a result of bismuth (...) pi arene interactions and pi (...) pi intermolecular contacts. In the crystal structures of the polymorph 2b as well as for 4 bismuth (...) pi arene interactions are not observed, but both compounds revealed C-HPh (...) pi intermolecular contacts, as likewise observed in all of the three described polymorphs of Ph3Bi. For compound 3 intermolecular contacts as a result of coordination of the methoxy group to neighboring bismuth atoms are observed overruling Bi (...) pi arene contacts. Compound 5 shows a combination of donor acceptor Bi (...) Cl and Bi (...) pi arene interactions, resulting in an intermolecular pincer-type coordination at the bismuth atom. A detailed analysis of three polymorphs of Ph3Bi (1), which were chosen as model systems, at the DFT-D level of theory supported by DLPNO-CCSD(T) calculations reveals how van der Waals interactions between different structural features balance in order to stabilize molecular arrangements present in the crystal structure. Furthermore, the computational results allow to group this class of compounds into the range of heavy main group element compounds which have been characterized as dispersion energy donors in previous work.

KW - arylbismuth compounds

KW - DFT-D

KW - dispersion type Bi (...) pi arene interaction

KW - DLPNO-CCSD(T)

KW - electronic structure calculations

KW - polymorphism

KW - single crystal X-ray structure

KW - ORBITAL COUPLED-CLUSTER

KW - GROUP VB ELEMENTS

KW - BISMUTH COMPOUNDS

KW - ORGANIC DERIVATIVES

KW - MOLECULAR-STRUCTURE

KW - CRYSTAL-STRUCTURE

KW - MAIN-GROUP

KW - CHEMISTRY

KW - TRIPHENYLBISMUTH

KW - COORDINATION

U2 - 10.3762/bjoc.14.187

DO - 10.3762/bjoc.14.187

M3 - Article

VL - 14

SP - 2125

EP - 2145

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -