Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues

doi:10.1134/S1063774506030126

Title: Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues

Full Record
Similar

Abstract

A comparative study of the molecular geometry and crystal packing of crown-containing styryl heterocycles and their dimethoxy substituted analogues is performed. It is established that all the compounds exhibit an identical type of distortions of the geometry of the central styryl fragment. These are the localization of the {pi}-electron density at the ethylene bond and the bond alternation in a half of the phenyl ring due to the conjugation of lone electron pairs of the oxygen substituents with the chromophore system of the molecule. A comparative analysis of the crystal packings of the compounds reveals extended separate hydrophilic and hydrophobic regions. The hydrophilic regions are built of crown ether fragments, and the hydrophobic regions consist of {pi}-conjugated and aromatic molecular fragments. The hydrophobic regions are characterized by a wide variety of packing motifs, among which stacking packing is absent. For two compounds, the formation of sandwich dimers that are preorganized to enter into the photochemical [2 + 2]cycloaddition reaction is observed.

Authors:

Kuz'mina, L. G. ^[1]; Fedorova, O. A.; Andryukhina, E. N.; Mashura, M. M.; Gromov, S. P.; Alfimov, M. V. ^[2]

Russian Academy of Sciences, Kurnakov Institute of General and Inorganic Chemistry (Russian Federation), E-mail: kuzmina@igic.ras.ru
Russian Academy of Sciences, Photochemistry Center (Russian Federation)

Publication Date:: Mon May 15 00:00:00 EDT 2006

OSTI Identifier:: 21091479

Resource Type:: Journal Article

Resource Relation:: Journal Name: Crystallography Reports; Journal Volume: 51; Journal Issue: 3; Other Information: DOI: 10.1134/S1063774506030126; Copyright (c) 2006 Nauka/Interperiodica; Article Copyright (c) 2006 Pleiades Publishing, Inc; Country of input: International Atomic Energy Agency (IAEA)

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; CROWN ETHERS; CRYSTALS; ELECTRON DENSITY; ELECTRON PAIRS; ETHYLENE; MOLECULAR STRUCTURE; PHOTOCHEMISTRY

Citation Formats


                    Kuz'mina, L. G., Fedorova, O. A., Andryukhina, E. N., Mashura, M. M., Gromov, S. P., and Alfimov, M. V. Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues.  United States: N. p., 2006. 
        Web.  doi:10.1134/S1063774506030126.

Copy to clipboard


                    Kuz'mina, L. G., Fedorova, O. A., Andryukhina, E. N., Mashura, M. M., Gromov, S. P., & Alfimov, M. V. Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues.  United States.  doi:10.1134/S1063774506030126.

Copy to clipboard


                    Kuz'mina, L. G., Fedorova, O. A., Andryukhina, E. N., Mashura, M. M., Gromov, S. P., and Alfimov, M. V. Mon .  
        "Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues".  United States.  
        doi:10.1134/S1063774506030126.

Copy to clipboard


                    
@article{osti_21091479,

  title        = {Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues},

  author       = {Kuz'mina, L. G. and Fedorova, O. A. and Andryukhina, E. N. and Mashura, M. M. and Gromov, S. P. and Alfimov, M. V.},

  abstractNote = {A comparative study of the molecular geometry and crystal packing of crown-containing styryl heterocycles and their dimethoxy substituted analogues is performed. It is established that all the compounds exhibit an identical type of distortions of the geometry of the central styryl fragment. These are the localization of the {pi}-electron density at the ethylene bond and the bond alternation in a half of the phenyl ring due to the conjugation of lone electron pairs of the oxygen substituents with the chromophore system of the molecule. A comparative analysis of the crystal packings of the compounds reveals extended separate hydrophilic and hydrophobic regions. The hydrophilic regions are built of crown ether fragments, and the hydrophobic regions consist of {pi}-conjugated and aromatic molecular fragments. The hydrophobic regions are characterized by a wide variety of packing motifs, among which stacking packing is absent. For two compounds, the formation of sandwich dimers that are preorganized to enter into the photochemical [2 + 2]cycloaddition reaction is observed.},

  doi          = {10.1134/S1063774506030126},

  journal      = {Crystallography Reports},

  number       = 3,

  volume       = 51,

  place        = {United States},

  year         = {Mon May 15 00:00:00 EDT 2006},

  month        = {Mon May 15 00:00:00 EDT 2006}

}

Copy to clipboard

Journal Article:

DOI: 10.1134/S1063774506030126

Other availability

Find in Google Scholar

Search WorldCat to find libraries that may hold this journal

Save / Share:

Export Metadata

Save to My Library

Crystal and molecular structure of [Cp[sub 2]Mo[sub 2](CO)[sub 4]([mu]-[eta][sup 1]:[eta][sup 2]-C[triple bond]CCH[sub 2]OMe)][Na(15-crown-5)]

Curtis, M.D. ; Meyer, A. ; Butler, W.M. - Organometallics; (United States)

The transformations of hydrogen-poor hydrocarbyls (C[sub n]H[sub x], x [le] n) on multimetallic sites are of interest in connection with the study of surface cokes and carbides formed during catalytic reactions of hydrocarbons or CO on metal surfaces. The authors have shown previously that an [alpha]-substituted alkyne complex is a convenient precursor to a metal-stabilized carbo-cation upon reaction with protic acids. During studies of the deprotonation reactions of dimolybdenum alkyne complexes, Green et al. published the results of their thorough investigation on this topic. In this paper, the authors report on the structure and fluxional behavior of the [sigma],[pi]-acetylide formedmore »« less
DOI: 10.1021/om00060a061
Crown ether alcohols. 1. Crystal and molecular structure of the complex between sym-hydroxydibenzo-14-crown-4- and water molecules ((C sub 18 H sub 20 O sub 5 )ter dot 1. 25(H sub 2 O)ter dot 0. 125(CH sub 3 OH)) including interesting water-methanol channels

Olsher, U. ; Frolow, F. ; Bartsch, R.A. ; ... - Journal of the American Chemical Society; (USA)

The synthesis and crystal structure of the title compound are described. Single-crystal x-ray structure analysis indicates 8 formula units in the unit cell of parameters a = 16.024 (1) {angstrom} and c = 13.076 (1) {angstrom}. The space group is I{bar 4}. Direct methods yielded the structure, which was refined by least-squares techniques to a final R factor of 0.038 for 1533 independent observations. Unusual water-methanol channels are found in this structure. The crystal packing of the complex includes hydrophilic water-methanol channels which are surrounded by hydrophobic cylinders consisting mainly of benzo rings and methylene groups. The crystal structure providesmore »« less
DOI: 10.1021/ja00208a015
f-Element/crown ether complexes. 10. Oxidation of UCl/sub 4/ to (UO/sub 2/Cl/sub 4/)/sup 2/minus// in the presence of crown ethers: Structural characterization of crown ether complexed ammonium ions ((NH/sub 4/)(15-crown-5)/sub 2/)/sub 2/(UO/sub 2/Cl/sub 4/) /times/2CH/sub 3/CN, ((NH/sub 4/)(benzo-15-crown-5)/sub 2/)/sub 2/(UCl/sub 6/) /times/ 4CH/sub 3/CN, and ((NH/sub 4/)(dibenzo-18-crown-6))/sub 2/(UO/sub 2/Cl/sub 4/) /times/ 2CH/sub 3/CN and synthesis of (Na(12-crown-4)/sub 2/)/sub 2/(UO/sub 2/Cl/sub 4/) /times/ 2OHMe and (UO/sub 2/Cl/sub 2/(OH/sub 2/)/sub 3/) /times/ 18-crown-6 /times/ H/sub 2/O /times/ OHMe

Rogers, R.D. ; Kurihara, L.K. ; Benning, M.M. - Inorg. Chem.; (United States)

Trace amounts of H/sub 2/O and limited exposure to air of reaction mixtures of UCl/sub 4/ and 12-crown-4, 15-crown-5, benzo-15-crown-5, 18-crown-6, or dibenzo-18-crown-6 in 1:3 mixtures of CH/sub 3/OH and CH/sub 3/CN resulted in the hydrolysis and oxidation of UCl/sub 4/ to (UO/sub 2/Cl/sub 4/)/sup 2/minus//. In the presence of these crown ethers, it has been possible to isolate intermediate products via crystallization of crown complexes of the (UO/sub 2/Cl/sub 4/)/sup 2/minus// ion, the (UCl/sub 6/)/sup 2/minus// ion, and (UO/sub 2/Cl/sub 2/(OH/sub 2/)/sub 3/). The neutral moiety crystallizes as a hydrogen-bonded crown ether complex; however, crown ether complexation of amore »« less
DOI: 10.1021/ic00273a014
Extraction of group 1-3 metals by F-substituted dithiophosphoric acids in the presence of crown ethers 18-crown-6 and 15-crown-5

Proyaev, V.V. ; Romanovskii, V.V. ; Maslennikov, I.G. - Radiochemistry

The radioactive tracers {sup 241}Am, {sup 152,154}Eu, {sup 144}Ce({sup 144}Pr), {sup 137}Cs, and {sup 85}Sr are used to determine the distribution coefficients of Am(III), Eu(III), Ce(III), Cs, and Sr on extraction from nitrate and chloride solutions by mixtures of F-substituted analogs of dithiophosphoric acids (F-DTPA) of general formula (H(CF{sub 2}CF{sub 2}){sub n}CH{sub 2}O){sub 2}P(S)SH (n = 1, 2, 3) and crown ethers 15-crown-5 (15C5) and 18-crown-6 (18C6). Higher selectivity is found for F-DTPA in the presence of 18C6 for Ce(III), Eu(III), and Am(III) as compared with 15C5. The extraction properties of F-DTPA are largely analogous to those of the strongmore »« less
The crystal structure and supramolecular chain of [La(NO{sub 3}){sub 3}(OH{sub 2}){sub 2}(phen)] {center_dot} 15-crown-5

Zhen Ping Ji ; Rogers, R.D. - Journal of Chemical Crystallography

[La(NO{sub 3}){sub 3}(OH{sub 2}){sub 2}(phen)]{center_dot} 15-crown-5 is hexagonal, P6{sub 5}, with a = 10.955(2), c =43.769(9) {Angstrom}, and D{sub calc} = 1.668 g cm{sup {minus}3} for Z = 6. In the complex, two nitrogen atoms (from phen) and eight oxygen atoms (six from three bidentate nitrate anions and two from water molecules) are coordinated to the central La(III) ion, forming a coordination polyhedron which is approximately a bicapped square antiprism. The coordinated water molecules donate hydrogen bonds to the oxygen atoms of the crown ether, forming polymeric hydrogen bonded chains which wrap helically along the unit cell direction c.