Organic Bismuth Compounds. I. Preparation of Tricarboxy-Triphenylbismuth Dichlorides and Certain Nitro-Triaryl Bismuth Compounds

Supniewski, J; Adams, Roger

doi:10.1021/ja01413a031

Cited by 43 publications

(29 citation statements)

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“…In order to develop a better understanding with regard to the effects of substituents, (C 6 H 4 -OMe-4) 3 Bi ( 3 ) [50–51] was prepared starting from BiCl 3 and the corresponding organolithium reagent following a general method as reported by Wang et al [52]. Compound 3 was obtained as colorless block-shaped crystals in yields of 83%.…”

Section: Resultsmentioning

confidence: 99%

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

Preda¹,

Krasowska²,

Wrobel³

et al. 2018

Beilstein J. Org. Chem.

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The dispersion type Bi···π 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···π 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)3Bi (2), (C6H4-OMe-4)3Bi (3), (C6H3-t-Bu2-3,5)3Bi (4) and (C6H3-t-Bu2-3,5)2BiCl (5). The structural analyses revealed that only two of them show London dispersion type bismuth···π arene interactions. One of them is the styryl derivative 2, for which two polymorphs were isolated. Polymorph 2a crystallizes in the orthorhombic space group P212121, while polymorph 2b exhibits the monoclinic space group P21/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–arenecentroid ribbons formed as a result of bismuth···π arene interactions and π···π intermolecular contacts. In the crystal structures of the polymorph 2b as well as for 4 bismuth···π arene interactions are not observed, but both compounds revealed C–HPh···π 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···π arene contacts. Compound 5 shows a combination of donor acceptor Bi···Cl and Bi···π 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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Section: Resultsmentioning

confidence: 99%

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

Preda¹,

Krasowska²,

Wrobel³

et al. 2018

Beilstein J. Org. Chem.

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“…This is evidence against artefactual production of acetaldehyde. Finding such a reactive aldehyde in urine and plasma was surprising, but it has been well documented in man and animals [12,14,15]. Raised levels may be due to increased production and/or to decreased metabolism to acetic acid.…”

Section: Discussionmentioning

confidence: 99%

3-Penten-2-one, a novel aldehyde adduct, is a biomarker for increased acetaldehyde in urine

Walker

Mills

Stansbridge

2009

Journal of Chromatography B

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“…Compounds 3b-3d were prepared in a similar manner, yields for 3b, 50%; 3c, 53%; 3d, 54%; hp for 3b, 174-176"/20 m m [13]; 3c, 30-33O11 mm; 3d, 90O10.2 mm; ir (potassium bromide): for 3c, 1753; 3d, 1749.…”

Section: -Phenanthrenecarbonyl Chloridementioning

confidence: 99%

Synthesis of 2‐ and 3‐substituted‐1,2,3,4‐tetrahydrodibenzo[f,h]isoquinolines

Grande

Trigo

Söllhuber

1986

Journal of Heterocyclic Chem

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Some 2‐ and 3‐substituted‐1,2,3,4‐tetrahydrodibenzo[f,h]isoquinolines were prepared by a synthetic scheme involving a selective Borch reduction of an amide to the corresponding amine and a Friedel‐Crafts cyclization to obtain the dibenzo[f,h]isoquinoline system. The title compounds, which have a similarity to the cell growth inhibitory alkaloid cryptopleurine, failed to exhibit significant protein synthesis inhibitory activity.

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Organic Bismuth Compounds. I. Preparation of Tricarboxy-Triphenylbismuth Dichlorides and Certain Nitro-Triaryl Bismuth Compounds

Abstract: ORGANIC BISMUTH COMPOUNDS. I 507 conditions. The reversal of the relative speeds of hydrolysis of lactose and maltose that was predicted by E. F. Armstrong and Caldwell has been realized. Washington, D. C.

Cited by 43 publications

References 0 publications

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

3-Penten-2-one, a novel aldehyde adduct, is a biomarker for increased acetaldehyde in urine

Synthesis of 2‐ and 3‐substituted‐1,2,3,4‐tetrahydrodibenzo[f,h]isoquinolines

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