Russian Chemical Bulletin, volume 60, issue 8, pages 1734-1761
Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 7.* Crystal structures of 4-styrylpyridine hydroperchlorates and solid-state [2+2] autophotocycloaddition reactions of these compounds
Kuz'mina L. G.
1
,
Vedernikov A.I.
2
,
Sazonov S K
2
,
Lobova N.A.
2
,
Churakov A.V.
1
,
Lermontova E Kh
1
,
Howard J. A. K.
3
,
Alfimov M.V.
2
,
Publication type: Journal Article
Publication date: 2011-08-01
Journal:
Russian Chemical Bulletin
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.7
ISSN: 10665285, 15739171
General Chemistry
Abstract
A series of 4-styrylpyridine hydroperchlorates were synthesized, and the [2+2] autophotocycloaddition (PCA) reaction in their polycrystalline films and single crystals resulting in the centrosymmetric rctt isomers of 1,2,3,4-tetrasubstituted cyclobutanes was investigated. Unlike neutral styrylpyridines, their protonated forms are better preorganized for the solid-state PCA reaction. According to the X-ray diffraction data, the cations of these compounds, like related styryl dyes, are mainly stacked in crystals in a head-to-head or head-to-tail fashion with equal probability. Only in the latter type of stacks, the PCA reaction is feasible as a single-crystal-to-single-crystal transformation. The crystal packing is stabilized by hydrogen bonds between organic cations and perchlorate anions, as well as by other weak directional interactions, for example, by S…S interactions, thus preventing the atomic displacements in the course of PCA. The completion of the PCA reaction in single crystals without their degradation was observed only for 15-crown-5-containing 4-styrylpyridine hydroperchlorate. The crystals of the latter compound are stabilized not by hydrogen bonds between the cations and anions but by N+-H…O(macrocycle) hydrogen bonds resulting in the formation of head-to-tail stacked dimers. In the crystals, these dimers are surrounded by a soft shell formed by rotationally and translationally mobile anions and benzene solvent molecules, as well as by conformationally flexible crown-ether moieties of adjacent dimer pairs. This leads to a decrease in the steric strain that occurs in the crystals in the course of PCA and prevents the degradation of single crystals. The PCA reaction is accompanied by the reduction in the crystal symmetry due to the doubling of the unit cell.
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- We do not take into account publications that without a DOI.
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Kuz'mina L. G. et al. Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 7.* Crystal structures of 4-styrylpyridine hydroperchlorates and solid-state [2+2] autophotocycloaddition reactions of these compounds // Russian Chemical Bulletin. 2011. Vol. 60. No. 8. pp. 1734-1761.
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Kuz'mina L. G., Vedernikov A., Sazonov S. K., Lobova N., Churakov A., Lermontova E. Kh., Howard J. A. K., Alfimov M., Gromov S. P. Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 7.* Crystal structures of 4-styrylpyridine hydroperchlorates and solid-state [2+2] autophotocycloaddition reactions of these compounds // Russian Chemical Bulletin. 2011. Vol. 60. No. 8. pp. 1734-1761.
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TY - JOUR
DO - 10.1007/s11172-011-0259-8
UR - https://doi.org/10.1007%2Fs11172-011-0259-8
TI - Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 7.* Crystal structures of 4-styrylpyridine hydroperchlorates and solid-state [2+2] autophotocycloaddition reactions of these compounds
T2 - Russian Chemical Bulletin
AU - Kuz'mina, L. G.
AU - Vedernikov, A.I.
AU - Sazonov, S K
AU - Lobova, N.A.
AU - Churakov, A.V.
AU - Lermontova, E Kh
AU - Howard, J. A. K.
AU - Alfimov, M.V.
AU - Gromov, S P
PY - 2011
DA - 2011/08/01 00:00:00
PB - Springer Nature
SP - 1734-1761
IS - 8
VL - 60
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2011_Kuz'mina,
author = {L. G. Kuz'mina and A.I. Vedernikov and S K Sazonov and N.A. Lobova and A.V. Churakov and E Kh Lermontova and J. A. K. Howard and M.V. Alfimov and S P Gromov},
title = {Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 7.* Crystal structures of 4-styrylpyridine hydroperchlorates and solid-state [2+2] autophotocycloaddition reactions of these compounds},
journal = {Russian Chemical Bulletin},
year = {2011},
volume = {60},
publisher = {Springer Nature},
month = {aug},
url = {https://doi.org/10.1007%2Fs11172-011-0259-8},
number = {8},
pages = {1734--1761},
doi = {10.1007/s11172-011-0259-8}
}
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Kuz'mina, L. G., et al. “Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 7.* Crystal structures of 4-styrylpyridine hydroperchlorates and solid-state [2+2] autophotocycloaddition reactions of these compounds.” Russian Chemical Bulletin, vol. 60, no. 8, Aug. 2011, pp. 1734-1761. https://doi.org/10.1007%2Fs11172-011-0259-8.