Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and crystal structures of three new benzotriazolylpropanamides.

ABSTRACT: The base-catalyzed Michael addition of 2-methyl-acryl-amide to benzotriazole afforded 3-(1H-benzotriazol-1-yl)-2-methyl-propanamide, C₁₀H₁₂N₄O (1), in 32% yield in addition to small amounts of isomeric 3-(2H-benzotriazol-2-yl)-2-methyl-propanamide, C₁₀H₁₂N₄O (2). In a similar manner, 3-(1H-benzotriazol-1-yl)-N,N-di-methyl-propanamide, C₁₁H₁₄N₄O (3), was prepared from benzotriazole and N,N-di-methyl-acryl-amide. All three products have been structurally characterized by single-crystal X-ray diffraction. The crystal structures of 1 and 2 comprise infinite arrays formed by N-H?O and N-H?N bridges, as well as ?-? inter-actions, while the mol-ecules of 3 are aggregated to simple ?-dimers in the crystal.

SUBMITTER: Amenta DS

PROVIDER: S-EPMC5458315 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis and crystal structures of three new benzotriazolylpropanamides.

Amenta Donna S DS Liebing Phil P Biero Julia E JE Sherman Robert J RJ Gilje John W JW Edelmann Frank T FT

Acta crystallographica. Section E, Crystallographic communications 20170526 Pt 6

The base-catalyzed Michael addition of 2-methyl-acryl-amide to benzotriazole afforded 3-(1H-benzotriazol-1-yl)-2-methyl-propanamide, C10H12N4O (1), in 32% yield in addition to small amounts of isomeric 3-(2H-benzotriazol-2-yl)-2-methyl-propanamide, C10H12N4O (2). In a similar manner, 3-(1H-benzotriazol-1-yl)-N,N-di-methyl-propanamide, C11H14N4O (3 ...[more]

PMID: 28638650

Similar Datasets

Synthesis, crystal structures, and Hirshfeld analysis of three hexahydroquinoline derivatives

Project description:Three hexahydroquinoline derivatives were synthesized and crystallized in an effort to study the structure–activity relationships of these calcium-channel antagonists. n these hexahydroquinoline derivatives, common structural features such as a flat-boat conformation of the 1,4-dihydropyridine (1,4-DHP) ring, an envelope conformation of the fused cyclohexanone ring, and a substituted phenyl group at the pseudo-axial position are retained. Hydrogen bonds are the main contributors to the packing of the molecules in these crystals. Three hexahydroquinoline derivatives were synthesized and crystallized in an effort to study the structure–activity relationships of these calcium-channel antagonists. The derivatives are ethyl 4-(2-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C22H27NO4, (I), ethyl 4-(4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C22H27NO4, (II), and ethyl 4-(3,4-dihydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C21H24NO5, (III). In these hexahydroquinoline derivatives, common structural features such as a flat-boat conformation of the 1,4-dihydropyridine (1,4-DHP) ring, an envelope conformation of the fused cyclohexanone ring, and a substituted phenyl group at the pseudo-axial position are retained. Hydrogen bonds are the main contributors to the packing of the molecules in these crystals.

| S-EPMC9638977 | biostudies-literature

Crystal structures of three new N-halo-methyl-ated quaternary ammonium salts.

Project description:In the crystals of the title N-halo-methyl-ated quaternary ammonium salts, C19H23IN(+)·I(-), (I) [systematic name: N-(4,4-di-phenyl-but-3-en-1-yl)-N-iodo-methyl-N,N-di-methyl-ammonium iodide], C20H25IN(+)·I(-), (II) [systematic name: N-(5,5-di-phenyl-pent-4-en-1-yl)-N-iodo-methyl-N,N-di-methyl-ammonium iodide], and C21H27IN(+)·I(-), (III) [systematic name: N-(6,6-di-phenyl-hex-5-en-1-yl)-N-iodo-methyl-N,N-di-methyl-ammonium iodide], there are short I⋯I(-) inter-actions of 3.564 (4), 3.506 (1) and 3.557 (1) Å for compounds (I), (II) and (III), respectively. Compound (I) crystallizes in the Sohncke group P21 as an 'enanti-opure' compound and is therefore a potential material for NLO properties. In the crystal of compound (I), mol-ecules are linked by C-H⋯I(-) and C-H⋯π inter-actions which, together with the I⋯I(-) inter-actions, lead to the formation of ribbons along [100]. In (II), there are only C-H⋯I(-) inter-actions which, together with the I⋯I(-) inter-actions, lead to the formation of helices along [010]. In (III), apart from the I⋯I(-) inter-actions, there are no significant inter-molecular inter-actions present.

| S-EPMC4647383 | biostudies-literature

Synthesis and crystal structures of two new tin bis-(carboranylamidinate) complexes.

Project description:Reaction of 2 equiv. of the lithium carboranylamidinate Li[o-(C2H10B10)C(NCy)(NHCy)] with SnCl2 in THF afforded the stannylene compound bis(N,N'-dicyclohexylamidinatocarboranate)tin(II), SnII[o-(C2H10B10)C(NCy)(NHCy)]2 (1). A similar reaction of SnCl4 with 2 equiv. of Li[o-(C2H10B10)C(N i Pr)(NH i Pr)] unexpectedly afforded the known solvated penta-chlorido-stannate(IV) salt [Li(THF)4][SnCl5(THF)] as the main reaction product. Small amounts of the new chlorido-tin(IV) bis-(carboranylamidinate) bis(N,N'-diiso-propylamidinatocarboranate)chloridotin(IV), SnIVCl[o-(C2H10B10)C(N i Pr)(NH i Pr)][o-(C2H10B10)C(N i Pr)2] (2), were isolated as a by-product. Single-crystal X-ray structure analysis revealed a ?C,?N-chelating coordination of the carboranylamidinate ligands in both 1 and 2. The Sn atom in 1 adopts a pseudo-trigonal-bipyramidal coordination under participation of a stereoactive lone pair. In 2, a trigonal-bipyramidal coordination of Sn is completed by a chlorido ligand.

| S-EPMC5730292 | biostudies-literature

Crystal structures of three bicyclic carbohydrate derivatives.

Project description:The title compounds, [(1R,3R,4R,5R,6S)-4,5-bis-(acet-yloxy)-7-oxo-2-oxabi-cyclo[4.2.0]octan-3-yl]methyl acetate, C14H18O8, (I), [(1S,4R,5S,6R)-5-acet-yloxy-7-hy-droxy-imino-2-oxobi-cyclo-[4.2.0]octan-4-yl acetate, C11H15NO6, (II), and [(3aR,5R,6R,7R,7aS)-6,7-bis-(acet-yloxy)-2-oxo-octa-hydro-pyrano[3,2-b]pyrrol-5-yl]methyl acetate, C14H19NO8, (III), are stable bicyclic carbohydrate derivatives. They can easily be synthesized in a few steps from commercially available glycals. As a result of the ring strain from the four-membered rings in (I) and (II), the conformations of the carbohydrates deviate strongly from the ideal chair form. Compound (II) occurs in the boat form. In the five-membered lactam (III), on the other hand, the carbohydrate adopts an almost ideal chair conformation. As a result of the distortion of the sugar rings, the configurations of the three bicyclic carbohydrate derivatives could not be determined from their NMR coupling constants. From our three crystal structure determinations, we were able to establish for the first time the absolute configurations of all new stereocenters of the carbohydrate rings.

| S-EPMC5137623 | biostudies-literature

Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes.

Project description:The present paper reports crystallographic studies on three related compounds that were of inter-est as precursors for synthetic and mechanistic work in organosulfur chemistry, as well as to model nitro-gen-protecting groups: (N-methyl-carbamo-yl)(tri-chloro-meth-yl)disulfane, C3H4Cl3NOS2, (1), (N-benzyl-carbamo-yl)(tri-chloro-meth-yl)disulfane, C9H8Cl3NOS2, (2), and (N-methyl-N-phenyl-carbamo-yl)(tri-chloro-meth-yl)disulfane, C9H8Cl3NOS2, (3). Their mol-ecular structures, with similar bond lengths and angles for the CCl3SS(C=O)N moieties, are confirmed. Compounds (1) and (3) both crystallized with two independent mol-ecules in the asymmetric unit. Classical hydrogen bonding, as well as chlorine-dense regions, are evident in the crystal packing for (1) and (2). In the crystal of (1), mol-ecules are linked via N-H⋯O hydrogen bonds forming chains along [110], which are linked by short Cl⋯Cl and S⋯O contacts forming sheets parallel to (001). In the crystal of (2), mol-ecules are linked via N-H⋯O hydrogen bonds forming chains along [001], which in turn are linked by pairs of short O⋯Cl contacts forming ribbons along the c-axis direction. In the crystal of (3), there are no classical hydrogen bonds present and the chlorine-dense regions observed in (1) and (2) are lacking.

| S-EPMC4647414 | biostudies-literature

Crystal structures of three sterically congested disilanes.

Project description:In the three sterically congested silanes, C24H38Si2 (1) (1,1,2,2-tetra-isopropyl-1,2-di-phenyl-disilane), C24H34Br4Si2 (2) [1,1,2,2-tetra-kis-(2-bromo-propan-2-yl)-1,2-di-phenyl-disilane] and C32H38Si2 (3) (1,2-di-tert-butyl-1,1,2,2-tetra-phenyl-disilane), the Si-Si bond length is shortest in (1) and longest in (2), with (3) having an inter-mediate value, which parallels the increasing steric congestion. A comparison of the two isopropyl derivatives, (1 and 2), shows a significant increase in the Si-C(ipso) distance with the introduction of bromine. Also, in the brominated compound 2, attractive inter-molecular Br⋯Br inter-actions exist with Br⋯Br separations ca 0.52 Å shorter than the sum of the van der Waals radii. In compound 2, one of the bromo-isopropyl groups is rotationally disordered in an 0.8812 (9):0.1188 (9) ratio. Compound 3 exhibits 'whole mol-ecule' disorder in a 0.9645 (7):0.0355 (7) ratio with the Si-Si bonds in the two components making an angle of ca 66°.

| S-EPMC5347074 | biostudies-literature

The crystal structures of three pyrazine-2,5-dicarb-oxamides: three-dimensional supra-molecular structures.

Project description:The complete mol-ecules of the title compounds, N2,N5-bis-(pyridin-2-ylmeth-yl)pyrazine-2,5-dicarboxamide, C18H16N6O2 (I), 3,6-dimethyl-N2,N5-bis-(pyridin-2-yl-meth-yl)pyrazine-2,5-dicarboxamide, C20H20N6O2 (II), and N2,N5-bis-(pyridin-4-ylmeth-yl)pyrazine-2,5-dicarboxamide, C18H16N6O2 (III), are generated by inversion symmetry, with the pyrazine rings being located about centres of inversion. Each mol-ecule has an extended conformation with the pyridine rings inclined to the pyrazine ring by 89.17 (7)° in (I), 75.83 (8)° in (II) and by 82.71 (6)° in (III). In the crystal of (I), mol-ecules are linked by N-H⋯N hydrogen bonds, forming layers lying parallel to the bc plane. The layers are linked by C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular structure. In the crystal of (II), mol-ecules are also linked by N-H⋯N hydrogen bonds, forming layers lying parallel to the (10-1) plane. As in (I), the layers are linked by C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular structure. In the crystal of (III), mol-ecules are again linked by N-H⋯N hydrogen bonds, but here form corrugated sheets lying parallel to the bc plane. Within the sheets, neighbouring pyridine rings are linked by offset π-π inter-actions [inter-centroid distance = 3.739 (1) Å]. The sheets are linked by C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular structure. Compound (I) crystallizes in the monoclinic space group P21/c. Another monoclinic polymorph, space group C2/c, has been reported on by Cockriel et al. [Inorg. Chem. Commun. (2008), 11, 1-4]. The mol-ecular structures of the two polymorphs are compared.

| S-EPMC5418794 | biostudies-literature

Synthesis and Crystal Structures of New Strontium Complexes with Aminoalkoxy and β-Diketonato Ligands.

Project description:New heteroleptic strontium complexes were synthesized using substitution reaction of bis(trimethylsilyl)amide of Sr(btsa)2·2DME with aminoalkoxide and β-diketonate ligands. The complexes [Sr(bdmp)(btsa)]2·2THF (1), [Sr(bdeamp)(btsa)]2 (2), [Sr(dadamb)(btsa)]2 (3), [Sr(bdmp)(hfac)]3 (4), [Sr(bdeamp)(hfac)]3 (5), [Sr(dadamb)(hfac)]3 (6), and [Sr3(dadamb)4(tmhd)2] (7) were prepared and characterized by means of various analysis techniques such as Fourier transform infrared, NMR, thermogravimetric analysis, and elemental analysis. Complexes 1-3 were further structurally confirmed by single-crystal X-ray crystallography, and they displayed dimeric structures in which strontium atoms were connected by alkoxide oxygen atoms of the μ2 type. Compound 1 has a trigonal prismatic structure, whereas 2 and 3 have a distorted square pyramidal structure. In complexes 5-7, trimeric structures were obtained with strontium atoms connected by μ3-O bonds of alkoxide oxygen atoms and μ2-O bonds of alkoxide and β-diketonate oxygen atoms. The crystal structures of 5, 6, and 7 showed distorted capped octahedral geometry, while 7 (middle Sr atom) displayed a distorted trigonal prism geometry. Complexes 5-7 displayed ∼70% mass loss in the temperature range from 25 to 315 °C.

| S-EPMC8223417 | biostudies-literature

Crystal structures of three newly synthesized flavanone hydrazones

Project description:The crystal structures of racemic mixtures of three new flavanone-hydrazones are reported: (±,E)-N′-[5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-ylidene]-2-(naphthalen-1-yl)acetohydrazide ethyl acetate monosolvate, (±,E)-N′-[5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-ylidene]-4-hydroxybenzohydrazide ethanol monosolvate and (±,E)-N′-(6-methoxy-2-phenylchroman-4-ylidene)-2-(naphthalen-1-yloxy)acetohydrazide. All three hydrazones are in the E isomeric form and exhibit a pucker at the chiral carbon atom. The naringenin-derived hydrazones both show intramolecular hydrogen bonding between the hydrazone nitrogen atom and a hydroxy group on the chromane ring. The crystal structures of racemic mixtures of three new flavanone-hydrazones in the centrosymmetric space group (P

| S-EPMC9993913 | biostudies-literature

Crystal structures of three hexakis-(fluoroar-yloxy)cyclo-triphosphazenes.

Project description:The syntheses and crystal structures of three cyclo-triphosphazenes, all with fluorinated ar-yloxy side groups that generate different steric characteristics, viz. hexa-kis-(penta-fluoro-phen-oxy)cyclo-triphosphazene, N3P3(OC6F5)6, 1, hexa-kis-[4-(tri-fluoro-methyl)-phen-oxy]cyclo-triphosphazene, N3P3[OC6H4(CF3)]6, 2 and hexa-kis-[3,5-bis(-tri-fluoro-methyl)-phen-oxy]cyclo-triphosphazene, N3P3[OC6H3(CF3)2]6 3, are reported. Specifically, each phospho-rus atom bears either two penta-fluoro-phen-oxy, 4-tri-fluoro-methyl-phen-oxy, or 3,5-tri-fluoro-methyl-phen-oxy groups. The central six-membered phosphazene rings display envelope pucker conformations in each case, albeit to varying degrees. The maximum displacement of the 'flap atom' from the plane through the other ring atoms [0.308 (5) Å] is seen in 1, in a mol-ecule that is devoid of hydrogen atoms and which exhibits a 'wind-swept' look with all the aromatic rings displaced in the same direction. In 3 an intra-molecular C-H(aromatic)⋯F inter-action is observed. All the -CF3 groups in 2 and 3 exhibit positional disorder over two rotated orientations in close to statistical ratios. The extended structures of 2 and 3 are consolidated by C-H⋯F inter-actions of two kinds: (a) linear chains, and (b) cyclic between mol-ecules related by inversion centers. In both 1 and 3, one of the six substituted phenyl rings has a parallel-displaced aromatic π-π stacking inter-action with its respective symmetry mate with slippage values of 2.2 Å in 1 and 1.0 Å in 3. None of the structures reported here have solvent voids that could lead to clathrate formation.

| S-EPMC6775729 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data