Vinyl Protons Research Articles

Parahydrogen-induced polarization enables the single-scan NMR detection of a 236 kDa biopolymer at nanomolar concentrations

Nuclear magnetic resonance (NMR) experiments utilizing parahydrogen-induced polarization (PHIP) were performed to elucidate the PHIP activity of the synthetic 236 kDa biopolymer poly-γ-(4-propargyloxy)-benzyl-L-glutamate) (PPOBLG). The homopolypeptide was successfully hyperpolarized and the enhanced signals were detected in 11.7 T solution NMR as a function of the PPOBLG concentration. The hydrogenation with parahydrogen caused signal enhancements of 800 and more for the vinyl protons of the side chain at low substrate concentration. As a result of this high enhancement factor, even at 13 nM of PPOBLG, a single scan 1H-NMR detection of the hyperpolarized protons was possible, owing to the combination of hyperpolarization and density of PHIP active sites.

Adiabatic Passage through Level Anticrossings in Systems of Chemically Inequivalent Protons Incorporating Parahydrogen: Theory, Experiment, and Prospective Applications.

Level anticrossings (LACs) are ubiquitous in quantum systems and have been exploited for spin-order transfer in hyperpolarized nuclear magnetic resonance spectroscopy. This paper examines the manifestations of adiabatic passage through a specific type of LAC found in homonuclear systems of chemically inequivalent coupled protons incorporating parahydrogen (pH2). Adiabatic passage through such a LAC is shown to elicit translation of the pH2 spin order. As an example, with prospective applications in biomedicine, proton spin polarizations of at least 19.8 ± 2.6% on the methylene protons and 68.7 ± 0.5% on the vinylic protons of selectively deuterated allyl pyruvate ester are demonstrated experimentally. After ultrasonic spray injection of a precursor solution containing propargyl pyruvate and a dissolved Rh catalyst into a chamber pressurized with 99% para-enriched H2, the products are collected and transported to a high magnetic field for NMR detection. The LAC-mediated hyperpolarization of the methylene protons is significant because of the stronger spin coupling to the pyruvate carbonyl 13C, setting up an ideal initial condition for subsequent coherence transfer by selective INEPT. Furthermore, the selective deuteration of the propargyl side arm increases the efficiency and polarization level. LAC-mediated translation of parahydrogen spin order completes the first step toward a new and highly efficient route for the 13C NMR signal enhancement of pyruvate via side-arm hydrogenation with parahydrogen.

“On Water” Effect for Green Click Reaction: Spontaneous Polymerization of Activated Alkyne with “Inert” Aromatic Amine in Aqueous Media

“On Water” Effect for Green Click Reaction: Spontaneous Polymerization of Activated Alkyne with “Inert” Aromatic Amine in Aqueous Media

Stable Open‐Shell IC‐Fused Fluorenyl Enabling Efficient Photothermal Conversion

2‐(3‐Oxo‐2,3‐dihydro‐1H‐inden‐1‐yli‐dene)malononitrile (IC) derivatives are popular and crucial acceptor building blocks for the construction of highly efficient n‐type organic semiconductors. However, it is still challenging to increase their relatively poor chemical stability and photostability, originating from their unstable vinyl protons. Herein, two stable acceptor–donor–acceptor narrow‐bandgap materials LY1 and LY2 via replacing the IC series end groups of typical nonfullerene acceptors with IC‐fused fluorenyls are reported. The enhanced conjugation and strong electron‐withdrawing capability enable LY1 and LY2 to show lower bandgap, a deeper lowest unoccupied molecular orbital energy level, enhanced electrochemical stability, and significantly improved photostability compared with IT‐4F and IT‐4Cl. Benefiting from the broadened absorption and promoted nonradiative transition, LY1 and LY2 display enhanced photothermal conversion performance, presenting as promising pure organic photothermal materials.

A convenient green method to synthesize β-carotene from edible carrot and nanoparticle formation

A simple green chemistry approach was used to synthesize β-carotene from edible carrot without using solvent and heat. In this study, beta-carotene was extracted from edible carrots through a natural extraction method with several physical technical steps. The extracted sample was isolated using high-performance liquid chromatography (HPLC). A β-carotene peak was detected from HPLC with an absorbance maximum (2.135 mAU). The absorption of UV-Visible spectrum indicated that beta-carotene absorbs most strongly between 230-300 and 400-500 nm. The functional groups, namely, C=C (1649 cm-1), =C-H (900-900 cm-1) vibrations of antisymmetric deformation of CH3 groups and CH2 groups (1350-1450 cm-1) of beta carotene were identified by using the FTIR test. The 537, 538, and 539 peaks for all carbon atoms (C-12), one of the 40 carbon atoms is (C-13) and two carbon atoms as (C-13) were indicated using FTMS. The resonance relates to the protons connected to methyl and methylene groups and those attributed to the vinylic protons (H-C=C) were observed between 1-2 and 5-6 ppm, respectively. The AFM images demonstrate that the structure of the beta-carotene is spherical, and the average diameter of this molecule is 37.22 nm. The findings of the analysis show that the extraction and isolation of β-carotene from the carrot extract was achieved.

A Comparative Study of Redox-Active Dithiafulvenyl-Functionalized 1,3,6,8-Tetraphenylpyrene Derivatives.

A series of 1,3,6,8-tetraphenylpyrene (TPPy) derivatives substituted with redox-active 1,4-dithiafulvenyl (DTF) groups was synthesized and characterized. The conformational properties of these DTF-TPPys and their TPPy precursors were assessed by X-ray single-crystal and nuclear magnetic resonance analyses. Their electronic and redox properties were examined by ultraviolet-visible absorption, fluorescence, and cyclic voltammetric analyses. The DTF substitution was found to strongly modify the absorption, emission, and electrochemical properties, while detailed effects can be linked to substitution patterns and alkyl side chains attached to the DTF groups. Furthermore, the DTF-TPPy derivatives showed sensitivity to acids; in particular, the vinylic proton of DTF group could undergo efficient proton/deuterium exchange with D2O in an acidic medium.

Crystal structure of (E)-doxepin hydrochloride, C19H22NOCl

The crystal structure of (E)-doxepin hydrochloride has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. (E)-doxepin hydrochloride crystallizes in space group P21/a (#14) with a = 13.78488(7), b = 8.96141(7), c = 14.30886(9) Å, β = 96.5409(5)°, V = 1756.097(12) Å3, and Z = 4. There is a strong discrete hydrogen bond between the protonated nitrogen atom and the chloride anion. There are six C–H⋯Cl hydrogen bonds between the methyl groups and the chloride, as well as additional hydrogen bonds from methylene groups and the vinyl proton. The hydrogen bonds are important in determining the solid-state conformation of the cation. The compound is essentially isostructural to amitriptyline hydrochloride. The powder pattern is included in the Powder Diffraction File™ as entry 00-066-1613.

Peculiarities of NMR 1Н spectra of 5-arylsulfonyl-1,5-diphenyl-1-penten-3-ones

Differential spectral parameters ∆δ n of 5-arylsulfonyl-1,5-diphenyl-1-penten-3-ones have been calculated. Such parameters are the differences between the two basic spectral parameters -δ n values in NMR 1 Н spectra. To analyze the parameters of 1 H NMR spectra, we used the values δ і of the shift of their centers. The displacements of signals of the methylene group CH 2 ∆δ´, the methine group CH ∆δ´´, the protons of the vinyl group ∆δ´´´ and ∆δ´´´´ relative to the unsubstituted 5-arylsulfonyl-1,5-diphenyl-1-pentene-3-one were analyzed. The effect of substituents was evaluated by the parameter Dd і , which was calculated as the difference of chemical shifts of the groups CH 2 , CH and vinyl protons for unsubstituted and substituted arylsulfonyl nuclei. Different correlation constants were used to perform correlation dependences: Hammett constants s p ; s + ;Okamoto-Brown constants s p + and constants s Ф . The maximum difference |Dδ´´| was observed for the methine group CH, much smaller |Dδ´| for the methylene group CH 2 , the smallest values - for |Dδ´´´| and |∆δ´´´´|, which characterize changes in the chemical shifts of vinyl protons. Different correlation constants s were used to perform correlation dependences, but the best correlations were observed for Hammett constants s n ; Okamoto-Brown constant s n + ; s + and constants s Ф . The best correlations with the substituent constants for these 1 H NMR spectra are observed for protons of the CH group, which is directly linked to the arylsulfonyl group. Note that for the CH 2 group an almost perfect correlation was obtained by subtracting the results of the methyl group. An interesting regularity was established that for vinyl protons, more distant from the arylsulfonyl group vinyl protons, obtained good linear correlations for the Hammett constants s п and s + with a high value of R (0.915 and 0.994). It is evident the transmission of electronic influence occurs through the aromatic nucleus and the SO 2 group due to the mesomeric effect, and the sulfonyl group is the active conductor of such influence. The effective usage of differential spectral parameters has been shown using particular spectral task for value of relation influence of atoms and space structure of molecules. Correlation dependences ∆δ–s for chemical shifts of proton signals in 1 H NMR spectra using basic constants s, which take into account resonant interactions, can be successfully used to predict the physicochemical characteristics of 5-arylsulfonyl-1,5-diphenyl-1-penten-3-ones. Keywords : arylsulfones, 1 H NMR spectra, basic and differential spectral parameters, correlation dependences.

Isolation and characterization of oleochemical compounds from watermelon seed

The common watermelon item (Citrullus lanatus) seeds were gained from castoffs verdant nourishments for use by decorating, sun ventilation and pulverizing. Light yellow-toned oil was gotten by dissolvable withdrawal using oil atmosphere and the going with traits were gotten using oil ether: pH, refractive rundown, thickness, dissolvable miscibility, coagulating temperature, fire nature, express gravity, streak point and warmth of consuming. With a shallow level of unsaturation, stepped level of smoothness, and proximity of raised degree of the sensible proportion of free unsaturated fats. The low assessment of the solidifying temperature of the oil offered a hint that the oil can be managed in various areas paying little heed to the qualification in temperature. The following level of linoleic destructive of the oil offers a hint of natural gradation of solidarity. Fatty esters are increasing expanding significance as a biodegradable swap for mineral oils. In some request regions, for example, cutting tool oil, gearbox, pressure-driven oils, and greases for raw petroleum creation, the oleochemical items are set up. Nonetheless, certain particular wellsprings of fatty esters are hitherto to be abused for this comparative reason. This exploration subsequently tests into one of the less used wellsprings of fatty esters in watermelon. The oil from the kernels demonstrations a top-notch yield presents significant utilitarian gatherings for change and thus was utilized to set up an assortment of oleochemicals which demonstrated excellence materials in contrast with the routinely utilized oils feed frameworks for oleochemicals after portrayal. The photopolymers acquired indicated piercing vinyl protons for consistent polymerize.

Facile NMR approach for profiling curcuminoids present in turmeric

Curcumin, together with demethoxycurcumin and bisdemethoxycurcumin as a whole called curcuminoids, is an active phytochemical constituent present in the turmeric. When it comes to their analysis, most will rely on UV–Visible spectroscopy, HPLC and LC-MS methods. Looking to improve productivity, time and simplicity, we are proposing a 1H NMR based approach for curcuminoids analysis and its applications to different geographical regions. In the present work, sample preparation protocol is reported for the simultaneous determination of curcuminoids using 1H NMR. For the quantification of curcuminoids, 6–7 ppm vinylic proton region in the 1H NMR spectrum was used, where acetone was observed as the suitable solvent in terms of curcuminoids solubility and proper resolution of peak. The result shows that curcumin (46.8–59.50%) was major among all varieties, followed by DMC (22.15–27.70%) and BDMC (17.52–30.29%) except in Andhrapradesh variety, where BDMC (30.29%) was more than DMC (22.89%). These studies were further supported by HPLC analysis.

Mechanism and Origin of Stereoselectivity in Chiral Phosphoric Acid-Catalyzed Aldol-Type Reactions of Azlactones with Vinyl Ethers.

The precise mechanism of the chiral phosphoric acid-catalyzed aldol-type reaction of azlactones with vinyl ethers was investigated. DFT calculations suggested that the reaction proceeds through a Conia-ene-type transition state consisting of the vinyl ether and the enol tautomer of the azlactone, in which the catalyst protonates the nitrogen atom of the azlactone to promote enol tautomerization. In addition, the phosphoryl oxygen of the catalyst interacts with the vinyl proton of the vinyl ether. The favorable transition structure features dicoordinating hydrogen bonds. However, these hydrogen bonds are not involved in the bond recombination sequence and hence the catalyst functions as a template for binding substrates. From the results of theoretical studies and experimental supports, the high enantioselectivity is induced by the steric repulsion between the azlactone substituent and the binaphthyl backbone of the catalyst under the catalyst template effect.

Green Approach Extraction of Perezone from the Roots of Acourtia platyphilla (A. Grey): A Comparison of Four Activating Modes and Supercritical Carbon Dioxide.

Perezone, a sesquiterpene quinone, is a very important molecule due to its pharmacological activities in addition to the fact that it is considered to be the first secondary metabolite isolated in the new world (America–Mexico, 1852). This study aims to offer a green comparative study about the extraction of the target molecule from the roots of the vegetable specimen Acourtia platyphilla (A. Grey). The study was performed comparing five different modes of extraction: supercritical CO2, electromagnetic infrared and microwave irradiations, mechanical-wave ultrasound versus typical mantle heating procedure. An exhaustive comparative-discussion of the obtained results is provided. It is worth noting that the corresponding quantifications were established using 1H NMR, correlating appropriately the integrals of the vinylic proton H-6 of perezone with the aromatic singlet of p-dinitrobenzene employed as an internal reference. It is also important to highlight that the four presented procedures are novel modes to extract perezone. Finally, a complementary study about the solubility of the target sesquiterpene quinone related to the use of supercritical CO2 is also reported.

Electronic structure and spectral characteristics of alkyl substituted imidazolium based dication-X2 (X = Br, BF4, PF6 and CF3SO3) complexes from theory

Electronic structure, cation-anion binding and spectral characteristics of the alkyl substituted imidazolium dication and Br−, BF4−, PF6− or CF3SO3− anion complexes have been obtained employing the M06-2X based density functional theory. The dication-anion complexes serve as model systems for describing dicationic ionic liquids and are facilitated by electrostatic, bifurcated hydrogen bonding (C-H⋯O) and anion---π interactions. The lowest energy conformer possesses relatively strong interactions from reactive vinylic protons on the imidazolium cation whereas the largely destabilized conformers reveal increasing contributions to binding from the interactions arising from by ethyl/butyl substituents at the expense of strong hydrogen bonding from vinylic protons on the imidazolium moiety. Underlying dication-anion binding has been probed through quantum theory of atoms in molecules (QTAIM) approach and the natural bond orbital analyses. It has been predicted that binding energies in the lowest energy complexes of the methyl substituted imidazolium complex emerge with a hierarchy: Br− > BF4− > CF3SO3− > PF6−, which is qualitatively different from that of butyl substituted complexes; the latter revealing stronger binding with CF3SO3− anion. The reactive vinylic proton engenders largely downfield δH signals (beyond 8.8 ppm) in their 1H NMR spectra. It has been further shown that hydrogen bond energies of the reactive proton (H1) estimated from the QTAIM theory correlate well with the 1H NMR chemical shifts measured from the experiments. The ramifications of dication-anion binding to vibrational spectra are also presented.

Physiochemical characterization of soybean oil derived silanized factice and its interaction with styrene butadiene rubber/silica composite

Abstract Soybean oil-based silanized factice (SF) was prepared and its compatibility with styrene butadiene rubber (SBR)/silica composite was evaluated. Characterization of SF, obtained by the inter-mixing of soybean oil (SBO), sulfur and bis-(3-(triethoxysilyl)-propyl) tetrasulfide (TESPT) with curing additives, was investigated and compared with the controlled factice (CF) which does not possess any TESPT. Free sulfur and acetone extract values of the SF were studied with varying TESPT content and optimum values were recorded. Structural differences were elucidated by attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR), where disappearance of peaks at 3010 cm−1 and 1650 cm−1 belonging to the stretching vibrations of the olefinic bonds in SBO, occurred with the formation of SF. The results were further confirmed by1H NMR spectroscopy where the signals corresponding to the vinylic and allylic protons were chemically shifted to 5.3 ppm and 2.8 ppm, respectively. Thermal changes were demonstrated with varying TESPT content. The morphology of the SF was elucidated by optical microscopy and scanning electron microscopy (SEM), which showed the fine structure following the addition of TESPT. Together with plasticization, the SF exhibited an excellent improvement in tensile strength compared with the SBR/silica composite due to the presence of interfacial interactions. This work proposes an approach to the preparation and characterization of bio-oil derived polymers for rubber composites.

Synthesis of copoly-(eugenol-stearyl acrylate) via cationic polymerization

Synthesis of copoly-(eugenol-stearyl acrylate)/Eg-co-SA was carried out through cationic copolymerization. Copolymerization was conducted using H2SO4 initiator, at room temperature (28-30 °C) and under nitrogen atmosphere. Structure of Eg-co-SA was identified by FTIR and 1H-NMR spectroscopy. Average molecular weight (Mv) of Eg-co-SA was measured by Ostwald Viscometer at constant temperature 28 °C. Morphology and thermal properties of Eg-co-SA was characterized using SEM and DSC. Analysis of EG-CO-SA structure by using FTIR showed disappear of characteristics absorption of the vinyl group (-CH=CH2) in 16381634 cm−1 and 998-977 cm−1 wave number. The success of synthesis was supported by the disappear of the 1H-NMR vinyl proton signal at 5.7-6.39 ppm and the appearance of new proton signal of single bond carbon (C-C) at 1-2.6 ppm. The increasing the weight of SA in Eg-co-SA synthesis gives changes in average molecular weight (Mv) and Degree of Polymerization (DP). The results of determining the average molecular weight of Eg-co-SA 2%, 4% and 5% were obtained 49812.10, 67709.25 and 75283.59 g/mol, respectively. Meanwhile, the degree of polymerization were 102, 139 and 154 for 2%, 4%, and 5% Eg-co-SA, respectively. Morphology of Eg-co-SA showed that increasing of SA weight resulted spongy surfaces with 0.35-10.46 μm diameter. Thermal analysis of Eg-co-SA showed that increasing of SA weight influenced thermal stability from 399 °C to 386 °C, when the SA content increase from 2% to 4%.

Application of a Stopped-Flow EPR Method for the Detection of Short-Lived Flavonoid Semiquinone Radicals Produced by Oxidation Using 15N-Labeled Nitrosodisulfonate Radical (Fremy’s Salt)

A stopped-flow-electron paramagnetic resonance (EPR) method was applied for the detection of short-lived radicals of flavonoids bearing a catechol moiety as the B-ring, such as flavonols (quercetin, fisetin, and rutin), flavanones (eriodictyol and taxifolin), flavanols (catechin and epicatechin), and flavone (luteolin). 15N-labeled sodium salt of nitrosodisulfonate (15NDS) was employed to obtain the highly resolved EPR hyperfine structure (hfs) of flavonoid-derived semiquinone radicals under stoichiometrically regulated reaction conditions in aqueous media (pH 10). The EPR hfs of these flavonoids radicals, except catechin and epicatechin, were recorded. Based on the g value and the proton hyperfine coupling constants (hfcc), these flavonoid-derived radicals were assigned to be semiquinone radicals of the catechol moiety (B-ring). For example, the observed EPR hyperfine structure (hfs) of the luteolin radical (Lut−·) was composed of four sets of doublet splitting, which could be ascribed to the three protons of the B-ring (a2′ = 0.136, a5′ = 0.102, and a6′ = 0.272 mT) and a vinyl proton of the C-ring (a3 = 0.099 mT). In addition, the characteristically small doublet splitting resolved for the fisetin anion radical (Fis−·, 0.028 mT) was assigned to the aromatic proton at the C5 carbon of the A-ring, indicating that the unpaired electron of the radials was partially delocalized onto the A-ring through the π bonds involved in the vinyl-carbonyl moiety of the C-ring. The hfcc of the methine protons at the C2 carbon of taxifolin and eriodictyol-derived radicals (Tax−· and Eri−·) was, respectively, evaluated to be 0.102 and 0.230 mT. The assignment of the proton hfcc of flavonoid-derived semiquinone radicals will be discussed in relation with the molecular structure of the C-ring.

Quantitative analysis of sugar ingredients in beverages and food crops by an effective method combining naphthimidazole derivatization and 1H-NMR spectrometry

Background: Though carbohydrates are needed for health, excessive uptake of sugar may induce obesity, decayed teeth, and chronic diseases. The Taiwan Food and Drug Administration has recently proposed to regulate common sugars, a list that includes glucose, galactose, fructose, lactose, maltose, and sucrose in beverages and dietary foods. Accordingly, rapid and effective methods are needed for the quantitative analysis of sugar ingredients in beverages and foods.Objective: To establish a convenient method of quantifying sugar ingredients in beverages and foods by using one-dimensional 1H-NMR spectroscopy via a simple treatment with naphthimidazole (NAIM) labeling kit.Methods: The sample of beverages or the hydrolysate of food crops were treated with an NAIM labeling kit that contains 2,3-naphthalenediamine and iodine in acetic acid solution. After the complete conversion of the reducing sugars to sugar-NAIM derivatives, the mixture solution was subjected to rotary evaporation under reduced pressure, and the residue was dissolved in D2O solution with dimethylsulfoxide (DMSO) as an internal standard for the 1H-NMR spectrometric analysis. Results: An aldose existing in two anomeric isomers is completely converted to the corresponding NAIM derivative that shows a single characteristic vinyl proton at a distinct position to facilitate the quantitative analysis by NMR spectrometry. Even 10 μmol of common sugar ingredients in 50 μL of beverage or in the hydrolysate prepared from 1 mg of food crop can be quantified.Conclusions: The results suggest that a simple treatment of beverage with the NAIM labeling kit provides a convenient method for the quantification of sugar ingredients by 1H-NMR spectrometry. This method combining NAIM derivatization and 1H-NMR analysis is also useful for the profiling and fingerprinting of food crops.Keywords: sugar, beverage, food crop, naphthimidazole, 1H-NMR spectrometry, quantitative analysis

Nanoscale nuclear magnetic resonance with chemical resolution.

Nuclear magnetic resonance (NMR) spectroscopy is a key analytical technique in chemistry, biology, and medicine. However, conventional NMR spectroscopy requires an at least nanoliter-sized sample volume to achieve sufficient signal. We combined the use of a quantum memory and high magnetic fields with a dedicated quantum sensor based on nitrogen vacancy centers in diamond to achieve chemical shift resolution in 1H and 19F NMR spectroscopy of 20-zeptoliter sample volumes. We demonstrate the application of NMR pulse sequences to achieve homonuclear decoupling and spin diffusion measurements. The best measured NMR linewidth of a liquid sample was ~1 part per million, mainly limited by molecular diffusion. To mitigate the influence of diffusion, we performed high-resolution solid-state NMR by applying homonuclear decoupling and achieved a 20-fold narrowing of the NMR linewidth.

Isolation and Elucidation of 15-Acetylguanacone from Soursop (<i>Annona muricata</i> Linn) Fruit and Molecular Docking Experiments

Annona muricata (Soursop) has attracted attention due to its content of annonaceous acetogenins, a large family of naturally occurring polyketides isolated from various species of the genus Annonaceae. The ethyl acetate fraction of Annona muricata was subjected to standard isolation protocol-gradient and isocratic silica gel column chromatography- to obtain three waxy and whitish amorphous compounds, 002/A1, 002/A2 and 002/C. The structure of compound 200/A2 was elucidated using 1H-NMR spectroscopy, infrared spectroscopy and electron impact (EI+) mass spectroscopy. The molecular weight of 200/A2 was determined as 662 by EI-MS ([M+H]+ : m/z = 662.1) leading to the molecular formula C39H66O8 as obtained using high resolution MS. The existence of an α, β-unsaturated γ-lactone moiety, non-hydroxylated at the C-4 position, was suggested by an IR carbonyl absorption at 1735.9 cm-1 and 1662.7 cm-1; the IR also gave signal for hydroxyl group at 3339.0 cm-1. The presence of a characteristic vinyl proton δ 7.24 (H-35, d), which is characteristic for α, β- unsaturated γ-lactone was confirmed by the 1H-NMR spectrum. The compound was thus elucidated to be 15-acetyl guanacone, an acetogenin. This acetogenin has not been reported in Annona muricata previously. The compound was subsequently subjected to molecular docking experiments which revealed that it targets and binds to vascular endothelial growth factor 2, VEGF2 (-8.5kcal/mole) and α1 β2 integrin (-6.8kcal/mole), This thus suggests that 15-acetyl guanacone prevents metastasis and invasion by cancer cells, and ultimately initiates apoptosis.Key words: VEGF2; Integrin; Cancer; Acetogenins; Apoptosis; Soursop.

Synthesis, Evaluation of Substituent Effect and Antimicrobial Activities of Substituted (E)-1-(3-bromo-4-morpholinophenyl)-3-phenylprop-2-en-1-one Compounds

A series of ten substituted (E)-1-(3-bromo-4-morpholinophenyl)-3-phenylprop-2-en-1-one compounds were synthesized by Crossed-Aldol condensation of 3-bromo-4-marpholino acetophenone with various substituted and unsubstituted benzaldehydes in presence of sodium hydroxide. The entire ten compounds are novel and these have been newly synthesized compounds. The synthesized substituted 3-phenylprop-2-en-1-one were characterized by their physical constants and UV, IR, NMR spectral data. These observed UV absorption maximum (λ max nm) value. The group frequencies of infrared absorption (cm -1 ) of νCO s-cis and s-trans, deformation modes of νCH out of plane and in-plane, νCH=CH out of plane, ν>C=C<out of plane values, 1 H chemical shifts (ppm) vinyl protons, 13 C chemical shifts (ppm) carbonyl carbons and vinyl carbons values were correlated with various Hammett substituent constants, and Swain-Lupton parameters using single and multi-regression analyses. From the results of statistical analysis, the effects of substituents on the functional group frequencies were studied. The antimicrobial activities of these synthesized substituted (E)-1-(3-bromo-4-morpholinophenyl)-3-phenylprop-2-en-1-ones have been screened using Kirby-Bauer method. DOI: http://dx.doi.org/10.17807/orbital.v9i1.852