DOCSLIB.ORG

Anthracene Related to Carcinogenicity1

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Anthracene Related to Carcinogenicity1 [CANCER RESEARCH 29,506—509,March1969] Molecular Site of Substituents of Benz(a)anthracene Related to Carcinogenicity1 JohnPatakiandCharlesHuggins The Ben May Laboratory for Cancer Research, The University ofChicago, Chicago, Illinois 60637 SUMMARY The tumor-producing effect of dibenz(a,h)anthracene led Cook (5) to undertake experiments showing that 9-isopropyl Benz(a)anthracene did not induce tumors in rats, but its BA is a (weak) carcinogenand Fieseret aL (9) synthesizedthe derivatives were highly and equally carcinogenic when they stronger cancer-producing substances 7-methyl-BA and possessed two or three methyl groups in any combination at 7,8-DMBA. Considerably later it was found that 7,12-DMBA the following special sites: positions 6, 7, 8, or 12. Derivatives (1), 7,8,12-TMBA (1), and 6,7,8-TMBA (21) are very powerful of benz(a)anthracene with pairs of methyl groups at sites 1 carcinogens. It was evident that substitution of BA at positions and 12 or 3 and 9 were not carcinogenic. 7,12-Dimethylbenz 7 and 8 to form cholanthrene or 7,8-DMBA was more effective (a)anthracene and 7,8,12-trimethylbenz(a)anthracene are in promoting carcinogenic potency than substitution of BA at equivalent in their ability to elicit neoplasms in rats and far positions 8 and 9 was, irrespective of whether a new ring was exceed 3-methylcholanthrene and benzo(a)pyrene in this formed or the substituents remained as alkyl groups. regard. MATERIALSANDMEThODS INTRODUCTION Chemicals. Of 26 compounds which were tested, four were In this paper it will be demonstrated that the addition of new. These were synthesized in our laboratories. The new one, two, or three small alkyl substituents at certain positions compounds (Table 2) are: 7-methoxy-12-methyl-BA (XVIII); in benz(a)anthracene is highly advantageous in transforming 7-ethoxy-12-methyl-BA (XIX); 6,7,12-TMBA (XXIV), and this molecule to an active carcinogen, whereas the introduc 6,8,12-TMBA (XXV). Satisfactory elemental analyses were ob tion of pairs of methyl groups into other sites was ineffective tamed for each compound. Their nuclear magnetic resonance in this regard. (NMR) spectra are in complete agreement with the assigned Kennaway and Cook made the basic discoveries in the sys structures. In addition, thin-layer chromatography (12) with tematic correlation of cancer-producing activity with chemical migration as a single spot was the minimum requirement for constitution. Benz(a)anthracene (7), benz(a)acridine (3) and purity of the compounds. benz(c)acridine (19) do not elicit cancer, but the ring system Lipid emulsions for i.v. injection were prepared by the of each is potentially carcinogenic, and cancer-producing prop method of Schurr (22). The hydrocarbon-concentration (w/w) erties are developed by substitution in suitable positions. The of our emulsions (Table 1) was: BA, BP, 3-MC, 0.25%; basic structures are activated to carcinogenic status by the 7,12-DMBA, 7,8,12-TMBA, 0.5%. addition of a supplementary ring or by the introduction of one Adrenal Apoplexy. Female rats of Sprague-Dawley strain or more small alkyl groups into the molecule. were injected i.v. with massive doses of each emulsion at 50 The strong 3-banded fluorescence spectrum of the carci days of age (Day 0); necropsy was performed on Day 3, and nogenic tars derived from isoprene and acetylene led to the the hemoglobin content of the adrenals was determined (16). identification of dibenz(a,h)anthracene (7) as the first pure Induction of Mammary Cancer. Normal female rats of aromatic carcinogen. It was found soon thereafter that 3- Sprague-Dawley strain weighing 140—160 gm were given a methylcholanthrene (24) and benzo(a)pyrene (6) greatly cx commercial ration (Rockland Mouse/Rat Diet, Tekiad, Inc., ceeded DBA2 in carcinogenic potency in the sense that these Monmouth, Illinois) and water ad libitum and kept in an air compounds gave rise to tumors more rapidly than DBA did. conditioned room at 25 ±1°C.Vaginal smears were examined daily. The rats remained healthy in the sense that (a) estrus cycles were regular and (b) there was no pulmonary disease. There were 8—10 animals in each group. ‘This investigation was supported by grants from American Cancer The animals were injected i.v. on 3 occasions with the lipid Society, Jane Coffin Childs Memorial Fund for Medical Research, and Walter Schwimmer. emulsion containing 2 mg of the hydrocarbon (approx. 13 2Abbreviations used: BA, benz(a)anthracene ; BP, benzo(a)pyrene; mg/kg) at 50 (Day 0), 53, and 56 days of age. The time of DBA, dibenz(a,h)anthracene;DMBA, dimethylbenz(a)anthracene; 3.MC, appearance of palpable mammary cancers was determined. The 3-methylcholanthrene ; TMBA, trimethylbenz(a)anthracene. animals were sacrificed on Day 98; active centers are mam Received September 3, 1968; accepted October 30, 1968. mary cancers found at necropsy. 506 CANCER RESEARCH VOL.29 Downloaded from cancerres.aacrjournals.org on October 1, 2021. © 1969 American Association for Cancer Research. Advantageous Carcinogenic Sites of Benz(a)anthracene Table 1Appearance ofpalpablecancers, days. ActiveNo. withMeancentersHydrocarbonratscancerRangeofRats S.D.(mean)Benz(a)anthracene280Benzo(a)pyrene30957—95 ± 1813-MC20744—98 71 ± 68±151.27,12-DMBA747428—58 35±76.97,8,12-TMBA202029—62 39 ±107.1 Mammary cancer evoked by pulse-doses of hydrocarbons. Female Sprague-Dawley rats, approx. 150 gm, on 3 occasions were given an intravenous injection of hydrocarbon respec tively at 50, 53, and 56 days of age respectively. Each dose of hydrocarbon was 2 mg (13 mg/kg). Active centers are cancers found at necropsy. See Footnote 2 for abbreviations. Induction of Sarcoma. Solutions of hydrocarbons (Table 2) of rats injected with 7-ethyl-BA (IV), 7-methoxy-BA (V), or in sesame oil, 0.5% w/v, were freshly prepared. The recipients 12-ethyl-BA (VIII). 7-Formyl-BA (VI) did not evoke tumors. were males, 25 days old (Day 0), Long-Evans strain; each was The following compounds (Table 2) with two alkyl groups injected i.m. in a hind leg with 0.5 ml of oil containing 2.5 mg were strong carcinogens, and sarcoma became evident in all of a compound. There were 8 animals in each group. The groups at about the same time: 6,7-DMBA (XI), 6,8-DMBA experiment was terminated on Day 270 when necropsy was (XII), 6,12-DMBA (XIII), 7,8-DMBA (XIV), 7,12-DMBA performed. (XV), 8,1 2-DMBA (XVI). 7-Methoxy-12-methyl-BA (XVIII), By our definition, a strong carcinogen induced sarcoma with 7-ethoxy-12-methyl-BA (XIX), and 7-formyl-1 2-methyl-BA in 6 months in every animal in a group of 8 rats; a weak (XXII)werealsostrongcarcinogens.Tworelatedcompounds, carcinogen elicited sarcoma more slowly and only in a propor 7,12-dimethoxy-BA (XX) and 7-hydroxymethyl-12-methyl-BA tion of the members of the group; a compound is inactive (XXI),wereweakcarcinogens. when no member of the group developed sarcoma in 9 Two derivatives of BA (Table 2) possessing pairs of methyl months. groups failed to cause sarcoma. The inactive compounds were 1,12-DMBA (IX) and 3,9-DMBA (X). 9,10-DMBA (XVII) was RESULTS a feeble carcinogen. Each of four derivatives of BA possessing three methyl Adrenal Effects. In the adult rat a single large dose of groups (Table 2) was a very strong carcinogen and equivalent 7,12-DMBA (16) and closely related compounds causes selec in the speed with which sarcoma became evident: 6,7,8-TMBA tive necrosis of the adrenal cortex with adrenal apoplexy. (XXIII), 6,7,12-TMBA (XXIV), 6,8,12-TMBA (XXV), and We found that an i.v. injection of a lipid emulsion of 7,8,12-TMBA (XXVI). 7,8,12-TMBA causes the same sort of adrenocorticolysis but less efficiently than 7,12-DMBA does. In female Sprague Dawley rats, 50 days old, the minimum quantity of hydrocar DISCUSSION bon to cause adrenal apoplexy in every member of a group of 4 animals was: 7,12-DMBA, 18 mg/kg; 7,8,12-TMBA, 90 The carcinogenicity of polycycic aromatic hydrocarbons for mg/kg. the rat was tested by 2 methods; each of these has advantages Adrenal hemorrhage was not observed in rats injected with peculiar to itself. emulsions of BA, BP, or 3-MC; in each case the dose of hydro The classical method (4) of intramuscular injection of solu carbon was 60 mg/kg. tions of hydrocarbons in oil is advantageous when the amount Mammary Cancer. A set of pulse-doses of 7,12-DMBA and of compound available is small; a pool of injected oil remains 7,8,12-TMBA evoked mammary cancer rapidly and in every for more than 1 year as a marker of the site of injection. But member of the group (Table 1). The number of active centers the development of sarcoma is slow and, as an additional dis was large and equal in rats injected with emulsions of each advantage, a pool of sesame oil in muscle can serve as a local compound (Table 1). Similar sets of pulse-doses of BP or 3-MC izing agent (14) for circulating carcinogens. The appearance of evoked mammary cancer respectively in 30 and 35% of the sarcoma in a small proportion of injected animals is not proof rats; the appearance of palpable tumors was delayed and the of carcinogenicity of the injected compound. yield of active centers was 1. Our emulsion of BA did not The use of injectable emulsions (15) of hydrocarbons is induce cancer.
Load more

Recommended publications
  • Reactivity and Functionalization of Naphthalene and Anthracene Complexes of {Tpw(NO)(Pme3)}
    Reactivity and Functionalization of Naphthalene and Anthracene Complexes of {TpW(NO)(PMe3)} Laura Jessica Strausberg Baltimore, Maryland B.A., Hollins University, 2008 A Dissertation presented to the Graduate Faculty of the University of Virginia in Candidacy for the Degree of Doctor of Philosophy Department of Chemistry University of Virginia July, 2013 ii Abstract Chapter 1 introduces the organic chemistry of aromatic hydrocarbons, with attention paid to regiochemical outcomes of organic reactions. The binding of naphthalene and anthracene to metal complexes is discussed, along with organic transformations they undergo as a result of their complexation. The previous work on osmium and rhenium complexes of naphthalene from the Harman group is explored. Finally, some spectroscopic techniques for exploring the chemistry of {TpW(NO)(PMe3)} complexes of naphthalene and anthracene are introduced. Chapter 2 discusses the highly distorted allyl complexes formed from {TpW(NO)(PMe3)} and the exploration of their origin. Attempts at stereoselectively deprotonating these cationic complexes is also discussed. 2 Chapter 3 describes our study of TpW(NO)(PMe3)(3,4-η -naphthalene)’s ability to undergo a Diels-Alder reaction with N-methylmaleimide. A solvent study suggested that this reaction proceeds by a concerted mechanism. To probe the mechanism further, we synthesized a series of methylated and methoxylated naphthalene complexes and measured their rates of reaction with N-methylmaleimide compared to the parent complex. We found that 1- substitution on the naphthalene increased the rate of cycloaddition, even if the substituent was in the unbound ring, while 2-substitution slowed the reaction rate when in the bound ring. This information is consistent with a concerted mechanism, as a 2-substituted product would be less able to isomerize to form the active isomer for the cycloaddition to occur.
    [Show full text]
  • Crystal Structure of Methyl 10-(Pyridin-4-Yl)-Anthracene-9
    Z. Kristallogr. NCS 2018; 233(3): 441–443 Xiang Huang and Da-Bin Shi* Crystal structure of methyl 10-(pyridin-4-yl)- anthracene-9-carboxylate, C21H15NO2 Table 1: Data collection and handling. Crystal: Block, colorless Size: 0.30 × 0.20 × 0.10 mm Wavelength: Mo Kα radiation (0.71073 Å) µ: 0.09 mm−1 Diffractometer, scan mode: Bruker SMART, φ and ω-scans θmax, completeness: 27.6°, >99% N(hkl)measured, N(hkl)unique, Rint: 9199, 3516, 0.027 Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2700 N(param)refined: 218 Programs: Bruker programs [1], SHELX [2, 3] before stirring for 2 h at 65 °C. Crude 10-bromo-anthracene- 9-carboxylic acid was precipitated by adding the acetic acid solution to 800 mL of ice/water slush, followed by suc- https://doi.org/10.1515/ncrs-2017-0334 tion filtration. The residue on the filter was dissolved in Received October 31, 2017; accepted February 20, 2018; available 500 mL of a 5% aquaeus solution of K2CO3 followed by online March 6, 2018 gravity filtration to remove undissolved side products such as 9,10-dibromoanthracene. The filtrate was acidified with Abstract concentrated HCl to precipitate crude 10-bromo-anthracene- Aba a = C21H15NO2, orthorhombic, 2 (no. 41), 22.149(2) Å, 9-carboxylic acid, which was recrystallized from 100 mL b = c = V = 3 Z = 13.2899(12) Å, 10.6679(10) Å, 3140.2(5) Å , 8, ethanol to yield 5.76 g of yellow needles. R F = wR F2 = T = gt( ) 0.0418, ref( ) 0.0953, 296(2) K.
    [Show full text]
  • Construction of Novel Molecular Architectures from Anthracene Units and Acetylene Linkers*
    Pure Appl. Chem., Vol. 84, No. 4, pp. 917–929, 2012. http://dx.doi.org/10.1351/PAC-CON-11-09-07 © 2012 IUPAC, Publication date (Web): 9 February 2012 Construction of novel molecular architectures from anthracene units and acetylene linkers* Shinji Toyota‡ Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan Abstract: To create novel π-conjugated compounds, we constructed various molecular archi- tectures from anthracene units and acetylene linkers. Several cyclic oligomers ranging from dimers to dodecamers were synthesized by macrocyclization of acyclic precursors with metal-catalyzed coupling reactions. The structures, dynamic behavior, and spectroscopic fea- tures were greatly influenced by the number of anthracene units and the combination of building units and linkers. Optically active and circular dichroism (CD)-active enantiomers of some chiral cyclic oligomers were resolved by chiral high-performance liquid chromato - graphy (HPLC). Conformational analysis of hexamers and higher oligomers was performed with the aid of density functional theory (DFT) calculations. Acyclic oligomers underwent reversible folding–unfolding processes via photochemical and thermal reactions. These results suggest that transannular π–π interactions between anthracene units are important fac- tors in controlling the structural and spectroscopic properties and functions of π-conjugated compounds. The scope and perspectives of this molecular design are discussed on the basis of previous studies. Keywords: aromatic compounds; alkynes; π–π interactions; stereochemistry; structure. INTRODUCTION In the chemistry of aromatic compounds, oligomeric structures consisting of simple repeating units are fascinating motifs for the creation of new compounds. The merits of this molecular design are the acces- sibility to a large number of compounds from simple building units as well as the ease of tuning elec- tronic properties by structural modifications.
    [Show full text]
  • Dissolved Organic Matter-Mediated Photodegradation of Anthracene and Pyrene in Water Siyu Zhao, Shuang Xue*, Jinming Zhang, Zhaohong Zhang & Jijun Sun
    www.nature.com/scientificreports OPEN Dissolved organic matter-mediated photodegradation of anthracene and pyrene in water Siyu Zhao, Shuang Xue*, Jinming Zhang, Zhaohong Zhang & Jijun Sun Toxicity and transformation process of polycyclic aromatic hydrocarbons (PAHs) is strongly depended on the interaction between PAHs and dissolved organic matters (DOM). In this study, a 125W high- pressure mercury lamp was used to simulate the sunlight experiment to explore the inhibition mechanism of four dissolved organic matters (SRFA, LHA, ESHA, UMRN) on the degradation of anthracene and pyrene in water environment. Results indicated that the photodegradation was the main degradation approach of PAHs, which accorded with the frst-order reaction kinetics equation. The extent of degradation of anthracene and pyrene was 36% and 24%, respectively. DOM infuence mechanism on PAHs varies depending upon its source. SRFA, LHA and ESHA inhibit the photolysis of anthracene, however, except for SRFA, the other three DOM inhibit the photolysis of pyrene. Fluorescence quenching mechanism is the main inhibiting mechanism, and the binding ability of DOM and PAHs is dominantly correlated with its inhibiting efect. FTIR spectroscopies and UV–Visible were used to analyze the main structural changes of DOM binding PAHs. Generally, the stretching vibration of N–H and C–O of polysaccharide carboxylic acid was the key to afect its binding with anthracene and C–O–C in aliphatic ring participated in the complexation of DOM and pyrene. Polycyclic aromatic hydrocarbons (PAHs) are typical persistent organic pollutants with two or more fused ben- zene rings that are widely distributed in multi-media, such as atmosphere, water, sediment, snow, and biota1–4.
    [Show full text]
  • Polycyclic Aromatic Hydrocarbons (Pahs)
    Polycyclic Aromatic Hydrocarbons (PAHs) Factsheet 4th edition Donata Lerda JRC 66955 - 2011 The mission of the JRC-IRMM is to promote a common and reliable European measurement system in support of EU policies. European Commission Joint Research Centre Institute for Reference Materials and Measurements Contact information Address: Retiewseweg 111, 2440 Geel, Belgium E-mail: [email protected] Tel.: +32 (0)14 571 826 Fax: +32 (0)14 571 783 http://irmm.jrc.ec.europa.eu/ http://www.jrc.ec.europa.eu/ Legal Notice Neither the European Commission nor any person acting on behalf of the Commission is responsible for the use which might be made of this publication. Europe Direct is a service to help you find answers to your questions about the European Union Freephone number (*): 00 800 6 7 8 9 10 11 (*) Certain mobile telephone operators do not allow access to 00 800 numbers or these calls may be billed. A great deal of additional information on the European Union is available on the Internet. It can be accessed through the Europa server http://europa.eu/ JRC 66955 © European Union, 2011 Reproduction is authorised provided the source is acknowledged Printed in Belgium Table of contents Chemical structure of PAHs................................................................................................................................. 1 PAHs included in EU legislation.......................................................................................................................... 6 Toxicity of PAHs included in EPA and EU
    [Show full text]
  • COMMUNICATION HACA’S Heritage: a Free Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars Tao Yang,[A] Ralf I
    COMMUNICATION HACA’s Heritage: A Free Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars Tao Yang,[a] Ralf I. Kaiser,[a]* Tyler P. Troy,[b] Bo Xu,[b] Oleg Kostko,[b] Musahid Ahmed,[b]* Alexander M. Mebel,[c]* Marsel V. Zagidullin[d] and Valeriy N. Azyazov[d] Abstract: The Hydrogen-Abstraction/Acetylene-Addition (HACA) mechanism has been central for the last decades in attempting to rationalize the formation of polycyclic aromatic hydrocarbons (PAHs) as detected in carbonaceous meteorites such as in Murchison. Nevertheless, the basic reaction mechanisms leading to the formation of even the simplest tricyclic PAHs like anthracene and phenanthrene are still elusive. Here, by exploring the previously unknown chemistry of the ortho-biphenylyl radical with acetylene, we deliver compelling evidence on the efficient synthesis of phenanthrene in carbon-rich circumstellar environments. However, the lack of formation of the anthracene isomer implies that HACA alone cannot be responsible for the formation of PAHs in extreme environments. Considering the Figure 1. Structures of biphenyl, naphthalene, acenaphthylene, overall picture, alternative pathways such as vinylacetylene- anthracene, and phenanthrene. mediated reactions are required to play a crucial role in the synthesis of complex PAHs in circumstellar envelopes of dying systems.[17-20] Based on electronic structure calculations[19, 21-24] and carbon-rich stars. kinetic modeling,[16, 25-29] HACA has been suggested to involve a repetitive sequence of atomic
    [Show full text]
  • A COMPARATIVE STUDY of TWO STAGE ELECTROCHEMICAL OXIDATION of ANTHRACENE, NAPHTHALENE and BENZENE USING Ce4+/Ce3+ REDOX SYSTEM
    Bulletin 0/ Electrochemistry 15 (7-8) Jul y-AugUSl 1999, pp 293-297 0256-1654/99/$ 3-50 © 19QQ CEeR [ A COMPARATIVE STUDY OF TWO STAGE ELECTROCHEMICAL OXIDATION OF ANTHRACENE, NAPHTHALENE AND BENZENE USING Ce4+/Ce3+ REDOX SYSTEM T VUAYARARATIII, R KANAKAM SRINIVASAN AND M NoF.L Central Ekctrodll'lllical Research Institute, Karaikudi 630000_ INDIA Two st.a~e electrochemical oxidation of anthracene, naphthalene and henzene were carried out to evaluate the relative ease of oxidation. Electrochemically generated Ce4+ species from sulphuric acid as well as methane sulphonic acid were employed to study the chemical oxidation step. The chemical step was carried out Iwth in the absence and in presence of added solvents such as dichloromethane and dichloroethane. 2.0 M methane sulphonic acid was found to be the medium of choice for the efficient oxidation of all the three compounds. Relatively higher reaction temperatures were reC(uind for the oxidation of naphthalene and henzene when compared to anthracene. In the case of henzene excess reactant itst'lf had to he used as a solvent. The reaction time was found to he considerably hi~her for henzene when compared to the other two compounds. Under optimum conditinns maximum yidd elf anthraquinune, naphthaquinone and benzoquinone were found to be 97%, 93% and 45% respectively. Keywords: Redo" system, electrochemical oxidation, polycylindro carbons INTRODUCTION present work wht'Tever possible efforts werc made to improve the yield and efficiency. 4 Ce + salts are known to he an efficient oxidising ag,'nt for EXI'ERIMENTAL the. oxidation of polycyclic hydrocarbons like anthracene and naphthalene [I-51.
    [Show full text]
  • Triplet States and Triplet Excitons in Chemically Mixed Crystals
    o (1995 ΛCA PHYSICA POLONICA A o 3 IE SAES A IE ECIOS I CEMICAY MIE CYSAS O ACIIE WI AACEE O MOAWSKI A OCOOW Isiue o ysics ois Acaemy o Sceces A oików 3/ - Wasawa oa (Received May 9, 1995) eicae o oessos Kyso igoń óe W oee a isław uiewic o e occasio o ei 7 iay? Seca a emoa caaceisics a ei emeaue eeece o e og-ie (osoescece a eaye uoescece emissioii o cemicay mie cysas o aciie II (os wi aacee (gues wee suie ue coiios o aious seca esouios a iee moes o eciaio e eegy o - asiios o ecio a a o a saes ae ee eemie a e aue a eegy sceme o e ie saes o cysas ae ee esaise e cke aageme o os moecues io wo iee ais i e cysa sucue o aciie II is eeae i e eegeic "oue" sucue o e a saes o o . e saow a e ee as (o aciie a o aacee oigi e- seciey Migaio o ie eciaioii eegy i ese cemicay mie cysas is cooe eomiay y e ie-ie aiiaio o ecios (eie eeogeeous o kogeeous amos i e woe em- eaue age e omaio o ie ecimes o aciie was eiiey ue ou ACS umes 317Ks 335q 7135+- 1 Ioucio Some ime ago e wo-comoe ogaic soi souios wi susiu- ioa isoe ie isooicay o cemicay mie moecua cysas seeme o e ey aacie as e moe sysems o igy isoee sysems (eg moecu- a gasses oymes a iquis [1] I as ue ou owee a i cemicay Sumie o iiaio o e Isiue o ysica a eoeica Cemisy ecica Uiesiy o Wocław Wocław oa (9 470 O.
    [Show full text]
  • Optimal Conditions for Treatment of Contaminated Waters with Anthracene by Fenton Processes in Close System Reactor Faiq F
    ISSN: 0974-2115 www.jchps.com Journal of Chemical and Pharmaceutical Science Optimal conditions for treatment of contaminated waters with anthracene by Fenton processes in close system reactor Faiq F. Karam*1 Falah H. Hussein2 Sadiq J. Baqir3 Ayad F. Alkaim4 *1 Chemistry Department, College of Science, Al-Qadisiyah University, Diwaniya 58002, Iraq 2 College of Pharmacy, Babylon University, Hilla 51002, Iraq 3 Chemistry Department, College of Science, Babylon University, Hilla 51002, Iraq 4 Chemistry Department, College of Science for women, Babylon University, Hilla 51002, Iraq *Corresponding author: E-mail: [email protected] Abstract Advanced Oxidation Processes such as Fenton, Photo-Fenton and Electro-Fenton have been applied effectively to remove the organic pollutants from the water and soil previously. Fenton reaction principle is based on the addition of hydrogen peroxide to the contaminated water or waste water in the presence ferrous salts as a catalyst to generate hydroxyl radicals. In this study, the effect of different parameters on the degradation by Fenton processes have been reported such as concentration of Anthracene, amount of FeSO4, pH value, temperature and hydrogen peroxide amount. The results indicate that the perfect conditions for degradation of Anthracene by Fenton -1 process were: Anthracene concentration 16 mg l , mass of FeSO4 = 120mg, pH of solution =4, temperature of solution 50 ₒC and Concentration of hydrogen peroxide = 150 mg l-1. KEYWORD: Fenton, pollution with PAHs, degradation of Anthracene, water treatment. 1. INTRODUCTION Polycyclic Aromatic Hydrocarbons (PAHs) are ubiquitous environmental contaminants that mainly originate by incomplete combustion of organic matter. Some of these have mutagenic and carcinogenic potentials(Paula 2009).
    [Show full text]
  • Liquid-Phase Oxidation of Anthracene in Acetic Acid with an Oxygen/Nitric Acid System
    J. Chem. Tech. Biotechnol. 1990, 49, 5544 Liquid-phase Oxidation of Anthracene in Acetic Acid with an Oxygen/Nitric Acid System C. K. Das & N. S. Das Central Fuel Research Institute, PO FRI, District Dhanbad, Bihar PIN 828 108, India (Received 18 September 1989; accepted 24 November 1989) ABSTRACT Oxidation of anthracene in acetic acid by the oxygenlnitric acid system has been studied and an attempt has been made to ascertain a practical limit of the amount of solvent keeping the commercial prospects in view. The effects of other reaction parameters such as flow rate, amount of nitric acid and water, residence time, etc., have been investigated. While opting for a solvent1 substrate ratio of 10, the optimum conversion of anthracene to anthraquinone fiee from nitro-compounds has been found to be 91 with purity of 98.7%, acceptable to dye-stuff industries. Key words: anthracene, anthraquinone, oxidation in liquid phase, oxygen, nitric acid. 1 INTRODUCTION Oxidation of anthracene in the liquid phase by nitric acid is a thermodynamically favourable reaction. Several attempts have been made earlier to develop the process, using this comparatively low-priced yet strongly oxidising agent to explore commercial viabilities.'" Oxidation with nitric acid alone is a stoichiometric reaction. Very dilute acid at lower temperature requires a long induction period, while with the use of strong nitric acid, the product purity may be affected, due to side reactions, such as nitration, which may also affect the overall economy of the process.'S2 However, nitric acid as co-oxidant with airloxygen has been found to be useful in oxidising anthra~ene.'.~.~The concentration of the acid requires proper adjustment to suppress the formation of undesired by-products and accordingly, an optimum limit has been suggested previously by the present authors.* In spite ofthe fact that the synthesis involves mild reaction conditions and simple techniques, thus 55 J.
    [Show full text]
  • DNA Interactions and Photocleavage by Anthracene, Acridine, and Carbocyanine-Based Chromophores
    Georgia State University ScholarWorks @ Georgia State University Chemistry Dissertations Department of Chemistry Fall 9-23-2013 DNA Interactions and Photocleavage by Anthracene, Acridine, and Carbocyanine-Based Chromophores Carla Mapp Follow this and additional works at: https://scholarworks.gsu.edu/chemistry_diss Recommended Citation Mapp, Carla, "DNA Interactions and Photocleavage by Anthracene, Acridine, and Carbocyanine-Based Chromophores." Dissertation, Georgia State University, 2013. https://scholarworks.gsu.edu/chemistry_diss/82 This Dissertation is brought to you for free and open access by the Department of Chemistry at ScholarWorks @ Georgia State University. It has been accepted for inclusion in Chemistry Dissertations by an authorized administrator of ScholarWorks @ Georgia State University. For more information, please contact [email protected]. DNA INTERACTIONS AND PHOTOCLEAVAGE BY ANTHRACENE, ACRIDINE, AND CARBOCYANINE-BASED CHROMOPHORES by CARLA TERRY MAPP Under the Direction of Dr. Kathryn B. Grant ABSTRACT The interaction of small molecules with DNA has been extensively studied and has produced a large catalogue of molecules that non-covalently bind to DNA though groove binding, intercalation, electrostatics, or a combination of these binding modes. Anthracene, acridine, and carbocyanine-based chromophores have been examined for their DNA binding properties and photo-reactivities. Their planar aromatic structures make them ideal chromophores that can be used to probe DNA structural interactions and binding patterns. We have studied DNA binding and photocleavgage properties of a bisacridine chromophore joined by a 2,6-bis(aminomethyl)pyridine copper-binding linker (Chapter II), a series of 9-aminomethyl anthracene chromophores (Chapters III and IV), both under conditions of high and low ionic strength, as well as a series of pentamethine linked symmetrical carbocyanine dyes (Chapter V).
    [Show full text]
  • Description of Aromaticity with the Help of Vibrational Spectroscopy: Anthracene and Phenanthrene Robert Kalescky, Elfi Kraka, and Dieter Cremer*
    Article pubs.acs.org/JPCA Description of Aromaticity with the Help of Vibrational Spectroscopy: Anthracene and Phenanthrene Robert Kalescky, Elfi Kraka, and Dieter Cremer* Computational and Theoretical Chemistry Group (CATCO), Department of Chemistry, Southern Methodist University, 3215 Daniel Avenue, Dallas, Texas 75275-0314, United States *S Supporting Information ABSTRACT: A new approach is presented to determine π-delocalization and the degree of aromaticity utilizing measured vibrational frequencies. For this purpose, a perturbation approach is used to derive vibrational force constants from experimental frequencies and calculated normal mode vectors. The latter are used to determine the local counterparts of the vibrational modes. Next, relative bond strength orders (RBSO) are obtained from the local stretching force constants, which provide reliable descriptors of CC and CH bond strengths. Finally, the RBSO values for CC bonds are used to establish a modified harmonic oscillator model and an aromatic delocalization index AI, which is split into a bond weakening (strengthening) and bond alternation part. In this way, benzene, naphthalene, anthracene, and phenanthrene are described with the help of vibrational spectroscopy as aromatic systems with a slight tendency of peripheral π-delocalization. The 6.8 kcal/mol larger stability of phenanthrene relative to anthracene predominantly (84%) results from its higher resonance energy, which is a direct consequence of the topology of ring annelation. Previous attempts to explain the higher stability of phenanthrene via a maximum electron density path between the bay H atoms are misleading in view of the properties of the electron density distribution in the bay region. ■ INTRODUCTION NMR chemical shift of an atomic nucleus is also affected by more π ff − The description of the chemical bond is one of the major than just -delocalization e ects.
    [Show full text]