Rosenmund-braun reaction products 4′,5′-dicyanobenzo-15-crown-5 and 4′,5′-dicyanobenzo-15-crown-5,4′-cyano-5′- cyano(bromo)benzo-15-crown-5 hydrates: Spectroscopic properties and crystal structure

Publication typeJournal Article
Publication date2005-09-26
scimago Q4
wos Q4
SJR0.189
CiteScore1.7
Impact factor1.1
ISSN10703284, 16083318
General Chemistry
General Chemical Engineering
Abstract
The products of 4′,5′-dibromobenzo-15-crown-5 (I) cyanation by the Rosenmund-Braun reaction are studied by the 1H NMR and IR spectroscopy methods. X-ray diffraction analysis of two isolated products, i.e., di(4′,5′-dicyanobenzo-15-crown-5) 1.6 hydrate {(CN)2B15C5}2 · 1.6H2O (IIa) and 4′,5′-dicyanobenzo-15-crown-5,4′-cyano-5′-cyano(bromo)benzo-15-crown-5 dihydrate (CN)3.85Br0.15(B15C5)2 · 2H2O (III) is performed. Crystals IIa are monoclinic, a = 15.882(2) Å, b = 11.412(2) Å, c = 18.484(3) Å, β = 100.717(3)°, V = 3291.7(9) Å3, Z = 4, space group P21/c, R = 0.0746 for 4775 reflections with I > 2σ(I). Crystals III are monoclinic, a = 15.956(3) Å, b = 11.425(2) Å, c = 18.865(4) Å, β = 99.32(3)°, V = 3394(1) Å3, Z = 4, space group P21/c, R = 0.0692 for 2070 reflections with I > 2σ(I). Compounds IIa and III have similar structures with two crystallographically independent molecules in each (A and B in IIa; C and D in III). Four of the five O atoms of a macrocycle in molecules A and C form hydrogen bonds with the water molecules. The latter molecules lie above and below the cycle plane at a distance of ∼2 Å from this plane. The A and C molecules have identical conformations (TTG TTG TTG TTG TTC) that differ from those of molecules B (TTG TGG STT SSG TTC) and D (TTC TSG STT SSG TTC).
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Minacheva L. Kh. et al. Rosenmund-braun reaction products 4′,5′-dicyanobenzo-15-crown-5 and 4′,5′-dicyanobenzo-15-crown-5,4′-cyano-5′- cyano(bromo)benzo-15-crown-5 hydrates: Spectroscopic properties and crystal structure // Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya. 2005. Vol. 31. No. 9. pp. 671-682.
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Minacheva L. Kh., Aleksandrov G., Lapkina L. A., Gorbunova Y. G., Demin S. V., Larchenko V. E., Sergienko V. S., Tsivadze A. Y. Rosenmund-braun reaction products 4′,5′-dicyanobenzo-15-crown-5 and 4′,5′-dicyanobenzo-15-crown-5,4′-cyano-5′- cyano(bromo)benzo-15-crown-5 hydrates: Spectroscopic properties and crystal structure // Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya. 2005. Vol. 31. No. 9. pp. 671-682.
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TY - JOUR
DO - 10.1007/s11173-005-0154-7
UR - http://link.springer.com/10.1007/s11173-005-0154-7
TI - Rosenmund-braun reaction products 4′,5′-dicyanobenzo-15-crown-5 and 4′,5′-dicyanobenzo-15-crown-5,4′-cyano-5′- cyano(bromo)benzo-15-crown-5 hydrates: Spectroscopic properties and crystal structure
T2 - Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya
AU - Minacheva, L Kh
AU - Aleksandrov, G.G.
AU - Lapkina, L A
AU - Gorbunova, Yu. G.
AU - Demin, S V
AU - Larchenko, V E
AU - Sergienko, V S
AU - Tsivadze, A. Yu.
PY - 2005
DA - 2005/09/26
PB - Springer Nature
SP - 671-682
IS - 9
VL - 31
SN - 1070-3284
SN - 1608-3318
ER -
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@article{2005_Minacheva,
author = {L Kh Minacheva and G.G. Aleksandrov and L A Lapkina and Yu. G. Gorbunova and S V Demin and V E Larchenko and V S Sergienko and A. Yu. Tsivadze},
title = {Rosenmund-braun reaction products 4′,5′-dicyanobenzo-15-crown-5 and 4′,5′-dicyanobenzo-15-crown-5,4′-cyano-5′- cyano(bromo)benzo-15-crown-5 hydrates: Spectroscopic properties and crystal structure},
journal = {Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya},
year = {2005},
volume = {31},
publisher = {Springer Nature},
month = {sep},
url = {http://link.springer.com/10.1007/s11173-005-0154-7},
number = {9},
pages = {671--682},
doi = {10.1007/s11173-005-0154-7}
}
MLA
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Minacheva, L. Kh., et al. “Rosenmund-braun reaction products 4′,5′-dicyanobenzo-15-crown-5 and 4′,5′-dicyanobenzo-15-crown-5,4′-cyano-5′- cyano(bromo)benzo-15-crown-5 hydrates: Spectroscopic properties and crystal structure.” Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya, vol. 31, no. 9, Sep. 2005, pp. 671-682. http://link.springer.com/10.1007/s11173-005-0154-7.