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    Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties / N. N. Golovnev [et al.] // J. Phys. Org. Chem. - 2018. - Vol. 31, Is. 3. - Ст. e3773, DOI 10.1002/poc.3773. - Cited References: 58. - The study was performed within the public task of the Ministry of Education and Science of the Russian Federation to the Siberian Federal University (4.7666.2017/BP) in 2017 to 2019. The reported study was funded by RFBR according to research projects 16-52-48010 and 17-52-53031. The X-ray data from single crystals were obtained with the use of the analytical equipment from the SB RAS Krasnoyarsk Center of collective use. . - ISSN 0894-3230
   Перевод заглавия: Две соли и соляной кристалл ципрофлоксацина с тиобарбитуровой и барбитуровой кислотами: структура и свойства
Кл.слова (ненормированные):
Barbituric and thiobarbituric acids -- Ciprofloxacin -- Infrared spectroscopy -- Salt cocrystal -- Thermal stability -- X-ray diffraction
Аннотация: Ciprofloxacin (CfH, C17H18FN3O3) crystallizes with 2-thiobarbituric (H2tba) and barbituric acid (H2ba) in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The compounds are structurally characterized by the X-ray single-crystal diffraction. The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba−/Hba− and CfH2+ ions, and H2ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2. There are different π-π interactions in 1 to 3. The compounds have been characterized by powder X-ray diffraction, thermogravimetry/differential scanning calorimetry, and Fourier transform infrared spectroscopy. The compounds dehydration ends at 130°C to 150°C, and their oxidative decomposition is observed in the range of 250°C to 275°C.

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Держатели документа:
Siberian Federal University Krasnoyarsk Russia
Laboratory of Crystal Physics Kirensky Institute of Physics, Federal Research Center KSC SB RAS Krasnoyarsk Russia
Department of Physics Far Eastern State Transport University Khabarovsk Russia
Laboratory of Optical Materials and Structures Institute of Semiconductor Physics SB RAS Novosibirsk Russia
Laboratory of Semiconductor and Dielectric Materials Novosibirsk State University Novosibirsk Russia

Доп.точки доступа:
Golovnev, N. N.; Molokeev, M. S.; Молокеев, Максим Сергеевич; Lesnikov, M. K.; Atuchin, V. V.
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Golovnev, N. N.
Crystal Structure and Properties of Levofloxacinium 2-Thiobarbiturate Trihydrate / N. N. Golovnev, M. S. Molokeev, M. K. Lesnikov // J. Struct. Chem. - 2018. - Vol. 59, Is. 3. - P. 646-651, DOI 10.1134/S0022476618030204. - Cited References: 20. - The work was performed within the State Task of the Ministry of Education and Science of the Russian Federation to the Siberian Federal University for 2017-2019 (4.7666.2017/BCh). . - ISSN 0022-4766. - ISSN 1573-8779

РУБ Chemistry, Inorganic & Nuclear + Chemistry, Physical
Рубрики:
CIPROFLOXACIN
   MONOHYDRATE
   QUINOLONE
   ACID
Кл.слова (ненормированные):
levofloxacin -- 2-thiobarbituric acid -- salt -- crystal structure -- absolute -- structure -- thermal stability -- IR spectrum
Аннотация: The structure of levofloxacinium 2-thiobarbiturate trihydrate LevoH 2 + Htba–·3H2O (I) (LevoH is levofloxacin, H2tba is 2-thiobarbituric acid) is determined (CIF file CCDC No. 1547466); its thermal decomposition and IR spectrum are studied. The crystals of I are triclinic: a = 8.670(1) Å, b = 9.605(1) Å, c = 15.786(2) Å, α = 89.144(5)°, β = 88.279(5)°, γ = 76.068(5)°, V = 1275.4(3) Å3, space group P1, Z = 2. The unit cell of I contains two LevoH 2 + ions, two Htba– ions, and six H2O molecules. The absolute structure of the crystal and the configuration of the chiral center in a levofloxacin molecule S are determined. Experiments for generating the second optical harmonics gave a positive result. Intermolecular hydrogen bonds (HBs) N–H···O and O–H···O in I form a bilayer system along the ab diagonal with hydrophilic moieties within a layer and hydrophobic moieties directed outward. The structure is stabilized by multiple HBs and the π–π interaction between the Htba–and LevoH 2 + ions and between the LevoH 2 + ions.

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Публикация на русском языке Головнёв Н. Н. Кристаллическая структура и свойства тригидрата 2-тиобарбитурата левофлоксациния [Текст] / Н. Н. Головнёв, М. С. Молокеев, М. К. Лесников // Журн. структ. химии. - 2018. - Т. 59 № 3. - С. 668-673

Держатели документа:
Siberian Fed Univ, Krasnoyarsk, Russia.
Russian Acad Sci, Kirensky Inst Phys, Siberian Branch, Krasnoyarsk, Russia.
Far Eastern State Transport Univ, Khabarovsk, Russia.

Доп.точки доступа:
Molokeev, M. S.; Молокеев, Максим Сергеевич; Lesnikov, M. K.; Ministry of Education and Science of the Russian Federation [4.7666.2017/BCh]
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548.737
К 82


    КРИСТАЛЛИЧЕСКАЯ СТРУКТУРА C17H20FN3O·CuBr·H2O [Текст] / А. Д. Васильев, Н. Н. Головнёв // Журнал структурной химии. - 2011. - Т. 52, № 4. - С. 829-832 . - ISSN 0136-7463
   Перевод заглавия: CRYSTAL STRUCTURE OF C17H20FN3O·CuBr·H2O

ГРНТИ	31
УДК	548.737

Рубрики:

Кл.слова (ненормированные):
fluoroquinolones -- ciprofloxacin -- bromide -- copper(ii) -- crystal structure -- hydrogen bonds -- фторхинолоны -- ципрофлоксацин -- бромид -- медь(ii) -- кристаллическая структура -- водородные связи
Аннотация: В кристаллической форме синтезировано новое соединение C17H20FN3O·CuBr·H2O, где C17H18FN3O3 (CfH, ципрофлоксацин) - 4-оксо-7-(1-пиперазинил)-6-фтор-1-циклопропил-1,4-дигидрохинолин-3-карбоновая кислота. Кристаллографические данные моногидрата тетрабромидокупрата(II) ципрофлоксациндиума, C17H22Br4CuFN3O4: a = = 8,214(1), b = 10,781(2), с = 13,703(2) A, ? = 85,144(2), ? = 79,119(2), ? = 84,018(2)°, V = 1182,5(4) A3, пр. гр. P, Z = 2. Супрамолекулярная архитектура кристалла отличается от установленной для C17H20FN3O·CuCl·H2O отсутствием ?-?-взаимодействий ароматических колец ионов CfH, а также структурными мотивами, образуемыми межмолекулярными водородными связями.
A new compound C17H20FN3O·CuBr·H2O is synthesized in the crystal form, where C17H18FN3O3 (CfH, ciprofloxacin) is 4-oxo-7-(1-piperazinyl)-6-fluoro-1-cyclopropyl-1,4-dihydroquinoline-3-carboxylic acid. Crystallographic data of ciprofloxacinium tetrabromocuprate(II) monohydrate, C17H22Br4CuFN3O4: a = 8.214(1) A, b = 10.781(2) A, с = 13.703(2) A, ? = 85.144(2)°, ? = 79.119(2)°, ? = 84.018(2)°, V = 1182.5(4) A3, space group, Z = 2. Supramolecular architecture of the crystal differs from that established for C17H20FN3O·CuCl·H2O by the absence of ?-? interactions of the aromatic rings of CfH ions and also the structural motifs formed by intermolecular hydrogen bonds.

РИНЦ
Держатели документа:
Сибирский федеральный университет

Доп.точки доступа:
Васильев, Александр Дмитриевич; Vasiliev, A.D.; Головнёв, Николай Николаевич; Golovnev, N.N.
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Preparation and crystal structure of hydrated crystalline complex of ciprofloxacin and copper tetrachloride / A. D. Vasil'ev [et al.] // J. Struct. Chem. - 2005. - Vol. 46, Is. 2. - P. 363-370, DOI 10.1007/s10947-006-0055-8. - Cited Reference Count: 16 . - ISSN 0022-4766
Аннотация: Synthesis of a complex formed by ciprofloxacin (cfH) and copper(II) chloride is described; its crystal structure is reported and analyzed in comparison to related compounds. The obtained compound (ctH(3))CuCl4 center dot H2O (cfH(3)(2+) - double protonated cfH molecule) crystallizes as platelets of P2(1)/c symmetry having the unit cell parameters a = 13.491 (1) angstrom, b = 11.0459(7) angstrom, c = 16.299(1) angstrom; beta = 1.392(7)degrees. Carbonyl oxygen O(1) is protonated, and hydrogen atom combined with it forms an intramolecular hydrogen bond with carboxylic O(2) oxygen (O(1) center dot center dot center dot O(2) = 2.642(5) angstrom). Terminal nitrogen atom N(3) of the piperazinyl group is also protonated, and two its hydrogen atoms participate in hydrogen bonds of N-H center dot center dot center dot Cl type. The structure also has hydrogen bonds O-H center dot center dot center dot O, O-H... Cl with the participation of water molecules which occupy hydrophilic channels. Molecular ions cfH(3)(2+), make couples with intrapair pi center dot center dot center dot pi interactions.

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Доп.точки доступа:
Vasil'ev, A. D.; Васильев, Александр Дмитриевич; Molokeev, M. S.; Молокеев, Максим Сергеевич; Golovnev, N.N.; Churilov, G. N.; Чурилов, Григорий Николаевич
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