Synthesis and characterization of various unsubstituted and mono-N-substituted tetraazamacrocycles

1995 ◽  
Vol 73 (5) ◽  
pp. 685-695 ◽  
Author(s):  
I. Meunier ◽  
A.K. Mishra ◽  
B. Hanquet ◽  
R. Guilard ◽  
P. Cocolios
Keyword(s):  
Mass Spectrometry ◽  
Template Synthesis ◽  
2D Nmr ◽  
Spectral Studies ◽  
Synthesis And Characterization ◽  
Difference Spectroscopy ◽  
Protective Group ◽  
Noe Difference Spectroscopy ◽  
C Nmr

Syntheses of tetraazamacrocycles have been carried out by using p-toluenesulfonyl chloride as protective group. The [14(ane) N4] and [15(ane) N4] were also obtained by the template synthesis. Mono-N-functionalization of tetraazamacrocycles was accomplished by reaction of a fivefold excess of the free macrocycles with 1 equivalent of a suitable alkylating or arylating reagent. The key point of the synthesis lies in the use of an excess of the macrocycle over the substituting reactants to reduce the formation of polysubstituted derivatives, and in the easy separation of the excess of unreacted macrocycle. All the products were characterized on the basis of spectral studies (1H and l3C NMR, including 2D NMR and NOE difference studies) and mass spectrometry. Keywords: tetraazamacrocycles, improved synthesis, protective group, N-tosylation, template synthesis, NOE difference spectroscopy.

Synthesis and characterization of a porphyrin-crown ether conjugate as a potential intermediate for drug delivery application

2020 ◽  
pp. A-G
Author(s):  
Maher Fathalla
Keyword(s):  
Mass Spectrometry ◽  
Drug Delivery ◽  
High Resolution Mass Spectrometry ◽  
Mesoporous Silica Nanoparticles ◽  
Synthesis And Characterization ◽  
Delivery Vehicle ◽  
Potential Applications ◽  
Resolution Mass ◽  
C Nmr

The development of synthetic strategies for functional building units plays a central role in supramolecular chemistry. Both porphyrin and crown ethers have attracted the attention of researchers worldwide owing to their unique properties. It is envisioned that the integration of the two molecules will result in hybrid materials with potential applications in many fields. In the present study, a new porphyrin derivative 3 appended with four 18-crown-6 (18C6) ether moieties was synthesized through the Suzuki-Miyaura coupling of boronic ester porphyrin 1 and 4-bromobenzo-18-crown-6 2 in 80% yield. Porphyrin 3 was fully characterized by 1H/[Formula: see text]C NMR spectroscopy and high resolution mass spectrometry. The tendency of the 18C6 to form host-guest complexes with ammonium cations was exploited to assemble cation responsive hybrid material of porphyrin 3 and ammonium immobilized mesoporous silica nanoparticles (MSNs). Furthermore, the potential application of the 3/MSNs conjugate as a cation-responsive drug delivery vehicle was investigated in solution by UV-vis and fluorescence spectroscopies.

Synthesis and ‎characterization ‎of a new acid ‎molten salt and ‎the study of ‎its ‎thermal ‎behavior and ‎catalytic ‎activity ‎in Fischer ‎esterification ‎

2021 ◽  
Author(s):  
Lia Zaharani ◽  
Nader Ghaffari Khaligh ◽  
Mohd Rafie Johan ◽  
Hayedeh Gorjian
Keyword(s):  
Mass Spectrometry ◽  
Catalytic Activity ◽  
Thermal Behavior ◽  
Molten Salt ◽  
Structure Elucidation ◽  
Chemical Structure ◽  
2D Nmr ◽  
Synthesis And Characterization ◽  
Fischer Esterification

A new acid molten salt was ‎‎prepared and its structure ‎‎elucidation was conducted ‎‎by FTIR, ‎‎1D NMR, 2D NMR, ‎‎and mass spectrometry. ‎Further support to ‎elucidate the chemical ‎structure of...

Two Xanthones from Polygala paniculata and Confirmation of the 1-Hydroxy- 2,3,5-trimethoxy-xanthone at Trace Level by HRGC-MS

2003 ◽  
Vol 58 (7-8) ◽  
pp. 490-494 ◽  
Author(s):  
Rodrigo Cristiano ◽  
Moacir G. Pizzolatti ◽  
Franco Delle Monache ◽  
Claudia M. Rezende ◽  
Alexsandro Branco
Keyword(s):  
Mass Spectrometry ◽  
Gas Chromatography ◽  
High Resolution ◽  
Spectroscopic Methods ◽  
Difference Spectroscopy ◽  
Trace Level ◽  
High Resolution Gas Chromatography ◽  
Posterior Analysis ◽  
Noe Difference Spectroscopy ◽  
C Nmr

Abstract Polygala paniculata L. yielded the xanthones 1-hydroxy-5-methoxy-2,3-methylenedioxyxanthone (1) and 1,5-dihydroxy-2,3-dimethoxyxanthone (2), together with coumarin murragatin and flavonol rutin. Their structures were established by chemical and spectroscopic methods (EIMS, IR, 1H and 13C NMR, NOE difference spectroscopy). By posterior analysis of an apolar crude extract using high resolution gas chromatography coupled to mass spectrometry (HRGC-MS) it was possible to characterize two sterol (spinasterol and Δ25-spinasterol) and the minor 1-hydroxy-2,3,5-trimethoxyxanthone (3). Thus, the xanthone 3 was confirmed through of co-injection HRGC-MS of the respective extract with a certified standard obtained by methylation of 2 with diazomethane.

Chemistry of the 1,3,5-Triaza-2-phosphorin-4,6-diones, Part XII*. Synthesis and Characterization of 2-PhenyI-2-(p-tolylthio)-1,3,5- trimethyI-1,3,5-triaza-4,6-dione-2-phosphorinonium Salts

1996 ◽  
Vol 51 (10) ◽  
pp. 1494-1500 ◽  
Author(s):  
Vasily A . Pinchuk ◽  
Ion Neda ◽  
Christian Müller ◽  
Holger Thönnessen ◽  
Peter G. Jones ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
New Products ◽  
Synthesis And Characterization ◽  
Tetrahedral Geometry ◽  
X Ray ◽  
Trigonal Bipyramidal ◽  
Weak Hydrogen Bonds ◽  
C Nmr

The reaction of 1,5-bis(trimethylsilyl)-1,3.5-trimethylbiuret (1) with p-tolylsulfenyl chloride (2) furnished l-(p-tolylthio)-5-trimethylsilyl-1,3,5-trimethylbiuret (3). In the reaction of 3 with phenyldichlorophosphine, 2-phenyl-2-(p-tolylthio)-1,3,5-trimethyl-1,3,5-triaza-4,6-dione- 2-phosphorinonium chloride (4) was formed. The same product was obtained from the reaction of 2-phenyl-1,3,5-trimethyl-1,3,5-triaza-2λ3- phosphorin-4,6-dione (6) with p-tolylsulfenyl chloride (2). Compound 4 was isolated and characterized in the form of the hexachloroantimonate (4a). The spirophosphorane 2-phenyl-1,3,5-trimethyl-1,3,5-triaza-7,10-dioxa-8,9- perchlorobenzo-2λ5-phosphaspiro-[4.5]decan-4,6-dione (7) was prepared by the reaction of 4 with tetrachloroorthobenzoquinone. The new products were characterized by 1H - and 13C NMR spectroscopy, elemental analysis, 31P NMR spectroscopy in the case of 4a. 6 and 7, and mass spectrometry (4a). Single-crystal X-ray structural analyses of compounds 4a and 7 were conducted. The phosphorus atom of 4a has the expected tetrahedral geometry, with a rather short P-S bond of 204.9(2) pm. In 7 the geometry at phosphorus is almost ideal trigonal bipyramidal. Weak hydrogen bonds are formed from a C (:O) group to deuterochloroform of solvation.

Synthesis and Characterization of Imidazolium Perrhenate Ionic Liquids

2013 ◽  
Vol 68 (5-6) ◽  
pp. 598-604 ◽  
Author(s):  
Shuang Yue ◽  
Da-Wei Fang ◽  
Jun Li ◽  
Shu-Liang Zang ◽  
Ming-Dong Zhou ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Alkyl Chain ◽  
Alkyl Chain Length ◽  
Synthesis And Characterization ◽  
Room Temperature Ionic Liquids ◽  
Ionization Mass ◽  
C Nmr

A series of air- and water-stable imidazolium perrhenate-based room-temperature ionic liquids [(RT)ILs] of the type [Cnmim][ReO4] (Cnmim = 1-CnH2n+1-3-methylimidazolium, n = 2, 4, 5, 6, 8, 10, 12) have been synthesized and characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, electrospray ionization mass spectrometry (ESI-MS), and elemental analysis (EA). The effect of the variation of the alkyl chain length on physical properties such as melting point, thermal stability, density, and conductivity was examined

Synthesis and Characterization of 1-Allyl-3,7,10-trimethylgermatrane and 1-Allylazagermatranes

1998 ◽  
Vol 53 (11) ◽  
pp. 1255-1258 ◽  
Author(s):  
Galina S. Zaitseva ◽  
Bettina A. Siggelkow ◽  
Sergey S. Karlov ◽  
Gleb V. Pen’kovoy ◽  
Jörg Lorberth
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Synthesis And Characterization ◽  
Elemental Analyses ◽  
New Compounds ◽  
C Nmr

The reaction between Br3GeAll (1) and N(CH2CHMeOSnBu3)3 (2, mixture of isomers) yielded N(CH2CHMeO)3GeAll (3) as a mixture of diastereomers. Three azagermatranes of the type N(CH2CH2NR)3GeAll (9, R = H; 10, R = Me; 11, R = Me3Si) have been synthesized from the reaction of (Me2N)3GeAll (5) with N (CH2CH2NHR)3 (R = H, 6; Me, 7; Me3Si, 8). Composition and structures of the new compounds were established by elemental analyses, 1H and 13C NMR spectroscopy and mass spectrometry.

Synthesis and Characterization of Chromium Tricarbonyl Complexes of 1-Phenylgermatrane and 1-Phenylazagermatrane. Crystal Structure of [N(CH2CH2O)3GeC6H5]Cr(CO)3

2002 ◽  
Vol 57 (9) ◽  
pp. 993-998 ◽  
Author(s):  
Sergey S. Karlov ◽  
Denis A. Sorokin ◽  
Yuri F. Oprunenko ◽  
Jörg Lorberth ◽  
Galina S. Zaitseva
Keyword(s):  
Crystal Structure ◽  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Synthesis And Characterization ◽  
Chromium Tricarbonyl ◽  
Elemental Analyses ◽  
Chromium Tricarbonyl Complexes ◽  
C Nmr

The reaction of 1-phenylgermatrane (1) and 1-phenylazagermatrane (2) with Cr(CO)6 affords chromium tricarbonyl complexes [N(CH2CH2O)3GeC6H5]Cr(CO)3 (6) and [N(CH2- CH2NH)3GeC6H5]Cr(CO)3 (7). In contrast, the same reaction of Cr(CO)6 with 1-(9-anthracenyl) germatrane (3) does not proceed. Composition and structures of the 6 and 7 were established by elemental analyses, 1H and 13C NMR spectroscopy and mass spectrometry. The crystal structure of 6 is reported

Synthesis and Characterization of a Methanofullerene-4-Fluoro-α-Cyanostilbene Dyad as a Potential Acceptor for Organic Solar Cells

2015 ◽  
Vol 1784 ◽  
Author(s):  
Venkata Neti
Keyword(s):  
Mass Spectrometry ◽  
Cyclic Voltammetry ◽  
Solar Cells ◽  
Organic Solar Cells ◽  
Synthesis And Characterization ◽  
Lumo Energy ◽  
Homo Lumo ◽  
Aryl Ester

ABSTRACTA series of fluorine appended highly conjugated fullerenes were prepared containing fluoro-α-cyanostilbene and aryl ester units. These modified PCBM dyads are fully characterized by NMR, Mass spectrometry, UV-vis, and cyclic voltammetry (Figures 1-4). It was found that the presence of fluoro-α-cyanostilbenes and esters affects the cyclic voltammetry and absorption in the UV-Vis region. The PCBA modified fullerenes significantly influences the HOMO-LUMO energy and wide absorption compared to PCBM.

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