DOCSLIB.ORG

Carcinogenesis of 4-(Hydroxymethyl)Benzenediazonium Ion (Tetrafluoroborate) of Agaricus Bisporus1

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Carcinogenesis of 4-(Hydroxymethyl)Benzenediazonium Ion (Tetrafluoroborate) of Agaricus Bisporus1 [CANCER RESEARCH 41, 2444-2449, June 1981] 0008-5472/81 /0041-0000 $02.00 Carcinogenesis of 4-(Hydroxymethyl)benzenediazonium Ion (Tetrafluoroborate) of Agaricus bisporus1 Bela Toth, Kasinath Patii, and Hwan-Soo Jae Eppley Institute for Research in Cancer and Allied Diseases, University of Nebraska Medical Center, Omaha, Nebraska 68105 ABSTRACT MATERIALS AND METHODS 4-(Hydroxymethyl)benzenediazonium tetrafluoroborate was Swiss albino mice from the colony randomly bred by us since administered as 26 weekly s.c. injections of 50 /ig/g body 1951 were used. They were housed in plastic cages with weight to randomly bred Swiss mice. In addition, as a solvent granular cellulose bedding, separated according to sex in control, sodium tetrafluoroborate was given as 26 weekly s.c. groups of 5, and given Wayne Lab-Blox diet in regular pellets injections at 25 fig/g body weight in 0.9% NaCI solution to (Allied Mills, Inc., Chicago, III.) and tap water ad libitum. another group of mice. The 4-(hydroxymethyl)benzenedi- The chemicals used were HMBD (Chart 1) (M.W. 221.96; azonium tetrofluoroborate treatment induced tumors in the m.p. 61-62°; purity, 95%) and STB (M.W. 103.79; m.p. 384° subcutis and skin in incidences of 20 and 12%, respectively; with decomposition; Alfa Division, Danvers, Mass.). HMBD was while in the solvent sodium tetrafluoroborate-injected mice, the synthesized in this laboratory in the following way. corresponding tumor incidences were 6 and 0%, respectively. A 1.75-g (1.5 mmol) sample of nitrosyl tetrafluoroborate was Histopathologically, the tumors were classified as a fibroma, suspended in 15 ml of ethyl acetate maintained at 0°. The fibrosarcomas, rhabdomyosarcomas, and an angiosarcoma in solution was cooled to —20°,and a solution of p-aminobenzyl the subcutis and also as squamous cell papillomas and carci alcohol in 15 ml of ethyl acetate was added in one portion. The nomas of the skin. mixture was stirred for 1 hr and filtered (yield, 2.0 g; purity, 4-(Hydroxymethyl)benzenediazonium ion is an ingredient of 90%; m.p. 51-52°). Recrystallization produced white crystals the cultivated mushroom of commerce Agaricus bisporus. (m.p. 61-62°). C7H7BF4N2O Calculated: C 37.84, H 3.15, N 12.61 INTRODUCTION Found: C 38.13, H 3.20, N 12.49 Evidence for the occurrence of 4-(hydroxymethyl)ben- 1H-nuclear magnetic resonance (D2O): «58.53 (d, J = 8.3 zenediazonium ion in basal-stalk sections of the commonly Hz, 2H); 7.90 (d, J = 8.3 Hz, 2H); 4.89 (s, 2H); 4.66 (broad s, cultivated mushroom of commerce Agaricus bisporus (Figs. 1 1H). IR (KBr): N = N 2275/cm. UV (H2O): e27425,000. and 2) was provided as early as 1962 (9). Also, the possibility A toxicity study was performed for 35 days before the was raised that this diazonium ion may be formed enzymatically chronic experiment. Five dose levels of HMBD such as 200, from agaritine, a constituent of this fungus (9). In addition, the 150, 100, 50, and 10 fig/g body weight were administered in presence of an enzyme y-glutamyltransferase (y-glutamyltran- 0.01 ml 0.9% NaCI solution as single s.c. injections to Swiss speptidase) was demonstrated, which catalyzes the hydrolysis mice. By taking into account 4 parameters (survival rates, body of agaritine to L-glutamate and 4-hydroxymethylphenylhydra- weights, dose of chemical, and histological changes), the 50- zine(7, 10). /xg/g body weight dose was found to be suitable for the chronic In earlier experiments, 4-methylphenylhydrazine, a water- treatment. This toxicity technique was developed in this labo soluble substance related to the aforementioned series of ratory (15). compounds, induced statistically significant incidence of soft- The chronic experimental group and the controls were as tissue tumors at injection sites when given by repeated s.c. follows. injection in mice (22, 28). From this finding, it was postulated Group 1. This consisted of 50 female and 50 male Swiss that a corresponding diazonium ion may have been formed mice, 6 weeks (43 days) old at the beginning of the experiment. locally and was ultimately responsible for cancer induction. They received 26 injections s.c. at weekly intervals of 50 jug This hypothesis was particularly promising, since none of the HMBD in 0.01 ml 0.9% NaCI solution per g body weight. other known carcinogenic water-soluble hydrazines had in Group 2. This consisted of 50 female and 50 male mice, 6 duced tumors at application sites (17, 18). weeks (44 days) old at the beginning of the experiment. They The present study thus demonstrates the tumorigenicity of HMBD2 administered by repeated weekly s.c. injections to received 26 injections s.c. at weekly intervals of 25 fig STB (this corresponds to an equimolar dose of the tetrafluoroborate Swiss albino mice. anión) in 0.01 ml 0.9% NaCI solution per g body weight. The experimental and control animals were carefully checked and weighed at weekly intervals, and the gross patho ' This study was supported by National Institute of Environmental Health logical changes were recorded. Complete necropsies were Sciences Contract NO1-CP05629 and was presented in part at the 71st Annual performed in all animals. All organs were examined macro- Meeting of the American Association for Cancer Research. San Diego, Calif., May 31, 1980(1). scopically and fixed in 10% buffered formalin. Histological 2 The abbreviations used are: HMBD. 4-<hydroxymethyl)benzenediazonium studies were done on the skin, subcutis, liver, spleen, kidneys, tetrafluoroborate; STB, sodium tetrafluoroborate; d, doublet; s. singlet. Received December 18. 1980; accepted March 13, 1981. bladder, thyroid, heart, pancreas, testes, ovaries, brain, nasal 2444 CANCER RESEARCH VOL. 41 Downloaded from cancerres.aacrjournals.org on September 30, 2021. © 1981 American Association for Cancer Research. Carcinogenesis of a Diazonium Salt turbinais, at least 4 lobes of the lungs of each mouse, and Finally, in 2 instances, rhabdomyosarcomas were observed those organs with gross pathological changes. Sections from which were composed of multinucleated giant cells and spindle these tissues were stained with hematoxylin and eosin. cells with the typical striations. Histopathologically, these le sions were similar to those described in humans (5). Tumors of Skin. Of the HMBD-treated females, 9 (18%) RESULTS developed such tumors at injection sites. Of these, 4 mice had The survival rates after weaning are recorded in Table 1. As squamous cell papillomas, 4 mice had squamous cell carcino can be seen from the data, the treatment shortened substan mas, and a mouse developed a squamous cell papilloma and tially the survival when compared with the solvent-injected a squamous cell carcinoma. In the HMBD-treated males, 3 controls. (6%) developed 3 skin tumors at the injection sites. Of these, The number, percentages of animals with tumors, and their 2 mice had squamous cell papillomas, and one mouse had a ages at death (latent periods) are summarized in Table 2. The squamous cell carcinoma. 2 most important neoplasms are described in detail below. No skin tumors were observed in the STB-injected mice of Tumors of s.c. Tissue. Of the HMBD-treated females, 11 both sexes. (22%) developed 13 such neoplasms at injection sites. Of Macroscopically, tumors of the skin exhibited localized over these, 10 mice had 11 fibrosarcomas, and one mouse devel growth of the epidermis capped often by keratinized material. oped a fibrosarcoma and an angiosarcoma. In the HMBD- They ranged from 3 to 15 mm in diameter (Fig. 6). These treated males, 9 (18%) developed 10 tumors at injection sites. tumors were classified into benign and malignant varieties. In These neoplasms consisted of 5 fibrosarcomas in 5 mice, 2 the squamous cell papillomas, the epithelial and fibrous com rhabdomyosarcomas in 2 mice, one angiosarcoma in one ponents were present in various proportions and were char mouse, and one fibrosarcoma and one angiosarcoma in one acterized by the papillary pattern of the proliferating, folded, mouse. and thickened epidermis (Fig. 7). In the squamous cell carci In the females given STB injections, 3 mice (6%) developed nomas, the irregular masses of the typical malignant epidermal tumors on the back, all classified as fibrosarcomas; while in cells descended downwards deep into the dermis (Fig. 8). the males given STB injections, 3 animals (6%) developed s.c. Macroscopically, these skin tumors were similar to those de tissue neoplasms, of which one was classified as a fibroma and scribed by other investigators in mice (3). the remaining 2 as fibrosarcomas. Other Tumors. A few other types of tumors were found also The connective tissue tumors were observed on the back in the treated groups shown in Table 2. Since they occurred in and on the side of the chest, exhibiting hard consistency and low incidences, their appearance cannot be attributed to the various shapes and sizes up to 60 mm in diameter. Sometimes treatment. the skin of the tumor was ulcerated (Fig. 3). The majority of these soft-tissue tumors were composed of the typical elon DISCUSSION gated spindle-shaped cells arranged in an interlacing fashion characteristic of fibrosarcomas (Fig. 4). The malignant tumor The current study demonstrates that HMBD, given as 26 also invaded the liver (Fig. 5). In a single instance, a benign weekly s.c. injections on a SO-jig/g body weight basis, induced variety of the connective tissue tumor, a fibroma was observed. tumors of the subcutis and skin in Swiss mice. The s.c. tissue It consisted of the cells of fibrous tissue with varying amounts tumor incidence rose from 6 to 22% (p < 0.046) in females of collagen and reticulin fibers. In a few instances, angiosar- and from 6 to 18% in males, whereas the skin tumor incidence comas were seen.
Load more

Recommended publications
  • A Study of the Decomposition of Some Aromatic Diazonium Hexafluorophosphate Salts
    University of Windsor Scholarship at UWindsor Electronic Theses and Dissertations Theses, Dissertations, and Major Papers 1-1-1964 A study of the decomposition of some aromatic diazonium hexafluorophosphate salts. William A. Redmond University of Windsor Follow this and additional works at: https://scholar.uwindsor.ca/etd Recommended Citation Redmond, William A., "A study of the decomposition of some aromatic diazonium hexafluorophosphate salts." (1964). Electronic Theses and Dissertations. 6038. https://scholar.uwindsor.ca/etd/6038 This online database contains the full-text of PhD dissertations and Masters’ theses of University of Windsor students from 1954 forward. These documents are made available for personal study and research purposes only, in accordance with the Canadian Copyright Act and the Creative Commons license—CC BY-NC-ND (Attribution, Non-Commercial, No Derivative Works). Under this license, works must always be attributed to the copyright holder (original author), cannot be used for any commercial purposes, and may not be altered. Any other use would require the permission of the copyright holder. Students may inquire about withdrawing their dissertation and/or thesis from this database. For additional inquiries, please contact the repository administrator via email ([email protected]) or by telephone at 519-253-3000ext. 3208. A STUDY OF THE DECOMPOSITION OF SOME AROMATIC DIAZONIUM HEXAFLUOROPHOSPHATE SALTS BY WILLIAM A. REDMOND A Thesis Submitted to the Faculty of Graduate Studies through' the Department of Chemistry in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy at the University of Windsor Windsor, Ontario 1964 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission.
    [Show full text]
  • Preparation of 5-Bromo-2-Naphthol: the Use of a Sulfonic Acid As a Protecting and Activating Group
    Molbank 2009, M602 OPEN ACCESS molbank ISSN 1422-8599 www.mdpi.com/journal/molbank Short Note Preparation of 5-Bromo-2-naphthol: The Use of a Sulfonic Acid as a Protecting and Activating Group Renata Everett, Jillian Hamilton and Christopher Abelt * Department of Chemistry, College of William and Mary, Williamsburg, VA 23187, USA * Author to whom correspondence should be addressed; E-mail: [email protected] Received: 2 June 2009 / Accepted: 25 June 2009 / Published: 29 June 2009 Abstract: The preparation of 5-bromo-2-naphthol (4) in three steps from 5-amino-2- naphthol (1) is described. A sulfonic acid group is introduced at the 1-position as an activating and protecting group for the Sandmeyer reaction. The sulfonate group allows for the use of only water and sulfuric acid as solvents. The sulfonic acid is introduced with three equivalents of sulfuric acid, and it is removed in 20% aq. sulfuric acid. Keywords: Sandmeyer reaction; protecting group; sulfonation; desulfonation 1. Introduction Regioselective synthesis of disubstituted naphthalenes can be challenging especially when the substituents are on different rings. We needed 5-bromo-2-naphthol (4) as a starting material for a multistep synthesis. This simple derivative is virtually unknown [1,2]. The most direct route to 4 is from 5-amino-2-naphthol (1) using the Sandmeyer reaction. Unfortunately, the Sandmeyer reaction fails with 1 because the hydroxyl group is too activating. Even when the hydroxyl group is protected as a methyl ether, the normal solution-phase Sandmeyer reaction employing cuprous salts is still problematic. In their preparation of 5-bromo-2-methoxynaphthalene, Dauben and co-workers resorted to pyrolysis of the diazonium ion double salt with HgBr2, but this procedure gives just a 30% yield of the bromide [3].
    [Show full text]
  • The Electrical Properties of Graphene Modified by Bromophenyl Groups
    CARBON 50 (2012) 1517– 1522 Available at www.sciencedirect.com journal homepage: www.elsevier.com/locate/carbon The electrical properties of graphene modified by bromophenyl groups derived from a diazonium compound Xiaochen Dong a, Qing Long a, Ang Wei a, Wenjing Zhang c, Lain-Jong Li c, Peng Chen b,*, Wei Huang a,* a Key Laboratory for Organic Electronics and Information Displays (KLOEID), Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications (NUPT), 9 Wenyuan Road, Nanjing 210046, China b School of Chemical and Biomedical Engineering, Nanyang Technological University, Singapore 637457, Singapore c Research Center for Applied Sciences, Academia Sinica, Taipei 11529, Taiwan ARTICLE INFO ABSTRACT Article history: Graphene field-effect transistors were fabricated with mechanically exfoliated single-layer Received 30 June 2011 graphene (SLG) and bilayer graphene (BLG) sheets and the functionalization effects of Accepted 15 November 2011 bromophenyl groups derived from a diazonium compound on its transfer properties were Available online 25 November 2011 explored. Spectroscopic and electrical studies reveal that the bromophenyl grafting imposes p-doping to both SLG and BLG. The modification of SLG by bromophenyl groups significantly reduces the hole carrier mobility and the saturation current in SLG transistors, suggesting an increase in both long-range impurity and short-range defect scattering. Unexpectedly, the bromophenyl group functionalization on BLG does not obviously increase both types of scattering, indicating that the BLG is relatively more resistant to charge- or defect-induced scattering. The results indicate that chemical modification is a simple approach to tailor the electrical properties of graphene sheets with different num- bers of layers.
    [Show full text]
  • Mechanistic Studies Into the Reactions of Diazonium And
    MECHANISTIC STUDIES INTO THE REACTIONS OF DIAZONIUM AND RELATED COMPOUNDS by CHARLES DOUGLAS MURRAY, B.Sc. Thesis presented for the degree of DOCTOR of PHILOSOPHY University of Edinburgh September 1974 GLBY TO MY PARENTS Douglas William and Isabella Seaton McKenzie Murray • • AND MY BROTHER • • William Graeme Murray I declare that this thesis is my own composition, that the work of which it is a record has been carried.out by myself, and that it has not been submitted in any previcis application for a Higher Degree. The thesis describes results of research carried out • in the Department of Chemistry, University of Edinburgh under the supervision of Professor J. I. G. Cadogan since the 1st October, • 1971, the date of my admission as a research student. The following is a statement of postgraduate courses attended during the last three years: Summer School in Mass Spectrometry, University of Sheffield, 26-30 March 1972; - Recent Developments in the Theory of Concerted Processes, Dr. A. J. Bellamy (five lectures); Organometallic Processes in Organic Chemistry, Professor P. L. Pauson (five lectures); Industrial Research and Development, Dr. B. Gravenor (five lectures); E. U. Chemistry Department Seminars (twenty-five periods). • ACKNOWLEDGEMENTS I should like to express my gratitude to Professor J. I. G. Cadogan for suggesting the topic of research and to Professor Cadogan and Dr. J. T. Sharp for their guidance and encouragement in all aspects of this work. I would also like to record my thanks and appreciation to various other members of Edinburgh University Chemistry Department: to Dr. R. M.Paton for advice and assistance related to e.
    [Show full text]
  • J.Phys. Chem. C 2016
    Article pubs.acs.org/JPCC Controlled Modification of Polymer Surfaces through Grafting of Calix[4]arene-Tetradiazoate Salts † ‡ ∥ ∥ ‡ Ludovic Troian-Gautier, Daniel E. Martínez-Tong, Julie Hubert, Francoiş Reniers, Michele Sferrazza, † § † Alice Mattiuzzi,*, Corinne Lagrost,*, and Ivan Jabin † Laboratoire de Chimie Organique, UniversitéLibre de Bruxelles (ULB), CP 160/06, 50 avenue F.D. Roosevelt, 1050 Brussels, Belgium ‡ Departement́ de Physique, Facultédes Sciences, UniversitéLibre de Bruxelles (ULB), CP 223, Campus de la Plaine, Boulevard du Triomphe, 1050 Brussels, Belgium § Institut des Sciences Chimiques de Rennes UMR n° 6226, Universitéde Rennes 1 and CNRS Equipe MaCSE, Campus de Beaulieu, Rennes 35042 Cedex, France ∥ Chimie Analytique et Chimie des Interfaces, UniversitéLibre de Bruxelles (ULB), CP 255, Campus de la Plaine, Boulevard du Triomphe, 1050 Brussels, Belgium *S Supporting Information ABSTRACT: An attractive methodology based on diazonium chemistry has been developed for the surface modification of polymers such as polypropylene (PP), polyethylene tereph- thalate (PET), and polystyrene (PS). The grafting procedure involves the in situ formation of diazoates in basic aqueous solution. The reactivity of calix[4]arene-tetradiazonium salts and a classical aryldiazonium salt was examined through comparative studies on gold and polymer surfaces. The surfaces were analyzed with a combination of techniques such as AFM, XPS, and ellipsometry. The results highlighted the fact that the calix[4]arene molecules are grafted as a robust and uniform monolayer both on gold and polymer surfaces, allowing a fine control over surface modification. Furthermore, the chemical postfunctionalization of the grafted calixarene platforms equipped with carboxylic-pendant groups was successfully performed with either an amine or an alcohol.
    [Show full text]
  • The Sandmeyer Reaction: Substitution for an NH2 on an Aromatic Ring
    Sandmeyer Reaction 59 The Sandmeyer Reaction: Substitution for an NH2 on an Aromatic Ring + General Sandmeier Reaction: Substitution for NH2 Group on a Benzene, via Diazonium ArN2 ArCN CuCN CuBr ArBr NaNO2, HCl HONO + - CuCl ArNH2 ArN2 Cl ArCl diazonium salt + H2O, H , heat ArOH H3PO2 ArH Intro The “Sandmeyer Reaction” is a versatile method for replacing the amine group of a primary aromatic amine with a number of different substitutents. The amine is treated with “nitrous acid” (HNO2) under acidic conditions, which produces the diazonium ion. The diazonium can then undergo substitution reaction with various reactants, particularly copper(I) substrates. Although the substitution can be simplistically viewed as a direct ionic substitution reaction (anion as nucleophile, molecular N2 as a premier leaving group), the actual mechanism is actually more complicated and involves radicals. HONO - Cl + NH2 NaNO2, HCl, H2O N2 Cl + N2 Sodium Nitrite CuCl mw = 69.1 g/mol copper(I) chloride p-chlorotoluene p-toluidine diazonium NaCl mw = 126.6 g/mol mw = 107.2 g/mol salt NaHSO bp = 162ºC mp = 45ºC 3 + NaOH density = 1.07 g/mL H2O, H , heat OH CuSO4-(H2O)5 copper(II) sulfate 249.7 g/mol Phenol Side Product Today’s Reaction: Synthesis of p-Chlorotoluene In today’s experiment, we will use copper(I) chloride (CuCl) as our “nucleophile”, to produce the chloride product. The diazonium ion has limited stability in water; it tends to react to give phenols (ArOH) upon standing or unnecessary warming. The principle organic side product will be the phenol resulting from competing reaction with water.
    [Show full text]
  • Diazonium Ion Assay Reagents and Methods for Their Use
    Patentamt Europaisches ||| || 1 1| || || || || || || || ||| ||| || (19) J European Patent Office Office europeen des brevets (11) EP 0 91 8 220 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication:ation: (51) |nt. ci.6: G01N 33/72, C07C 245/20 26.05.1999 Bulletin 1999/21 (21) Application number: 98121814.2 (22) Dateof filing: 17.11.1998 (84) Designated Contracting States: • Gordon, Tracey E. AT BE CH CY DE DK ES Fl FR GB GR IE IT LI LU Nobelsville, Indiana 46060 (US) MCNLPTSE • Bournique, Jennifer S. Designated Extension States: Indianapolis, Indiana 46239-9500 (US) AL LT LV MK RO SI • Walker, Sharanpal K. Indianapolis, Indiana 46620 (US) (30) Priority: 21.11.1997 US 975796 (74) Representative: (71) Applicant: Schwarz, Ralf, Dr. BOEHRINGER MANNHEIM CORPORATION Roche Diagnostics GmbH, Indianapolis, Indiana 46250-0528 (US) Patentabteilung, Sandhofer Strasse 116 (72) Inventors: 68305 Mannheim (DE) • Gnezda, Matthew F. Fishers, Indiana 46038 (US) (54) Diazonium ion assay reagents and methods for their use (57) Diazonium ions which are useful as reagents ducibly detected, and optionally correlated with the for the assay of bilirubin content in a sample, such as a presence or absence of any of a variety of diseases or body fluid sample, are provided. In one preferred disorders of organs such as the liver, gall bladder or embodiment, 2-methyl-3-nitroaniline diazonium ion is intestines. Using the assays, a wide range of different provided, having the structure: body fluid samples, such as urine, plasma or serum samples may be tested, and the interference in the assay from other components of the sample may be +N=N minimized.
    [Show full text]
  • Molecular Transport Properties Through Carbon Nanotube Membranes
    University of Kentucky UKnowledge University of Kentucky Doctoral Dissertations Graduate School 2007 MOLECULAR TRANSPORT PROPERTIES THROUGH CARBON NANOTUBE MEMBRANES Mainak Majumder University of Kentucky, [email protected] Right click to open a feedback form in a new tab to let us know how this document benefits ou.y Recommended Citation Majumder, Mainak, "MOLECULAR TRANSPORT PROPERTIES THROUGH CARBON NANOTUBE MEMBRANES" (2007). University of Kentucky Doctoral Dissertations. 557. https://uknowledge.uky.edu/gradschool_diss/557 This Dissertation is brought to you for free and open access by the Graduate School at UKnowledge. It has been accepted for inclusion in University of Kentucky Doctoral Dissertations by an authorized administrator of UKnowledge. For more information, please contact [email protected]. ABSTRACT OF DISSERTATION Mainak Majumder The Graduate School University of Kentucky 2007 MOLECULAR TRANSPORT PROPERTIES THROUGH CARBON NANOTUBE MEMBRANES ABSTRACT OF DISSERTATION A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the College of Engineering at the University of Kentucky By Mainak Majumder Lexington, Kentucky Director: Dr. Bruce J. Hinds, William Bryan Professor of Materials Engineering Lexington, Kentucky 2007 Copyright © Mainak Majumder 2007 ABSTRACT OF DISSERTATION MOLECULAR TRANSPORT PROPERTIES THROUGH CARBON NANOTUBE MEMBRANES Molecular transport through hollow cores of crystalline carbon nanotubes (CNTs) are of considerable interest from the fundamental and application point of view. This dissertation focuses on understanding molecular transport through a membrane platform consisting of open ended CNTs with ~ 7 nm core diameter and ~ 1010 CNTs/cm2 encapsulated in an inert polymer matrix. While ionic diffusion through the membrane is close to bulk diffusion expectations, gases and liquids were respectively observed to be transported ~ 10 times faster than Knudsen diffusion and ~ 10000-100000 times faster than hydrodynamic flow predictions.
    [Show full text]
  • Chemistry Unit 5
    EDEXCEL Advanced Level Edexcel IAL Chemistry Unit 2 Summary© HASAN SAYGINEL HS Redox and chemistry of the transition metals 1 Application of redox equilibria 1 TERMINOLOGY Oxidation number: The oxidation numbers of the elements in a compound are the charges they would have if the electrons in each bond of the molecule or ion belonged to the more electronegative element. The oxidation number of an ion is the number of electrons that have been removed (cation) or added (anion). The oxidation number of an uncombined element or compound is zero. • The oxidation number for an atom of any free (uncombined) element is ZERO. • The oxidation number of an element in self-combination is always ZERO. • In most hydrogen containing compounds, oxidation number of hydrogen is + 1.(Exception is when H combines with alkali metals or alkaline earth to form hydrides of metals such as: NaH, LiH, CaH2. Then, the oxidation number of H is -1). • In compounds involving the alkali metals, the elements are assigned oxidation number of +1. • In compounds involving the alkaline earth metals, the elements are assigned oxidation number of +2. • Oxygen is usually assigned an oxidation number of -2 for oxides. It has an oxidation number of -1 in peroxides (H2O2). • Fluorine always has oxidation number of -1 in compounds. The other elements in that group are usually -1 in compounds with elements of low electronegativity. • The sum of oxidation numbers of all the atoms in the formula for a neutral compound is ZERO. • The sum of oxidation numbers of an ion or complex ion is the same as the charge on that ion.
    [Show full text]
  • Understanding a Mild, Metal Free Reduction Method for the Large Scale Synthesis of Hydrazines
    Tetrahedron 67 (2011) 10296e10303 Contents lists available at SciVerse ScienceDirect Tetrahedron journal homepage: www.elsevier.com/locate/tet Piecing together the puzzle: understanding a mild, metal free reduction method for the large scale synthesis of hydrazines Duncan L. Browne *, Ian R. Baxendale, Steven V. Ley Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom article info abstract Article history: A key intermediate for the synthesis of hydrazines via a mild, metal free reduction of diazonium salts has Received 8 August 2011 been isolated and characterized by X-ray analysis. The presence of this intermediate is general, as Received in revised form 29 September 2011 demonstrated by the preparation of a number of analogues. A discussion of the mechanism and potential Accepted 30 September 2011 benefits of such a process are also described. Available online 12 October 2011 Ó 2011 Elsevier Ltd. All rights reserved. Dedicated to Professor Stork on the occasion of his 90th birthday Keywords: Hydrazines Vitamin C Ascorbic acid Diazonium salts X-ray 1. Introduction dicarbonyls (or equivalent surrogates) to provide pyrazoles, or by a Fischer indole synthesis employing the appropriate aldehyde or Of the top 200 selling pharmaceuticals in recent years, 20% of ketone (Fig. 1). Such synthesis methods are, however, not without the five-membered heterocyclic ring systems present are pyrazoles inherent problems, including relatively poor control over regiose- or indoles (Fig. 1).1 These motifs are usually derived from mono- lectivity. The requirement for the use of strong acid catalysis and substituted hydrazines either by condensation with 1,3- forcing reaction conditions is also of note particularly for the Fig.
    [Show full text]
  • US3215529.Pdf
    Nov. 2, 1965 R. M. LINDORUIST ETAL 3,215,529 COLOR PHOTOGRAPHIC MATERIAL Filed July 13, 1960 NE" 4. 2 8 22 INVENTORS /72aata 7/24 MMVAGeMM67 Az a ya //z Zay /777 Hur UA Cap/rcaya, ow "4e) 24%isATTORNEYS 3,215,529 United States Patent Office Patented Nov. 2, 1965 2 3,215,529 base is designated by the numeral 2, same being coated COLOR PHOTOGRAPHC MATERIAL on one side with a photosensitive layer 4 containing the Robert M. Lindquist, Lexington, Ky., Floyd T. Neth, leuconitrile color former. Typically, layer 4 may com Pensacola, Fla., and Arthur J. Critchlow, San Jose, prise a color former such as hydroxyethylate p-rosaniline Calif., assignors of one-half to Kalvar Corporation, leuconitrile, which gives a magenta image, in gelatin, New Orleans, La., a corporation of Louisiana, and of The superimposed coating 6 comprises the photosensitive one-half to International Business Machines Corpora layer which forms light scattering centers upon ex tion, San Jose, Calif., a corporation of New York posure to ultraviolet light above 3500A., and heat de Filed July 18, 1960, Ser. No. 43,374 velopment. Typically, this may comprise a suspension 7 Claims. (C. 96-27) 10 of light sensitive diazonium compound in a thermoplastic The present invention relates to a novel photographic polymer carrier such as "Saran' (vinylidene chloride color material. More particularly, the invention is con acrylonitrile copolymer) as described in Serial No. cerned with color photographic film comprising a plu 623,050. The other side of base 2 is coated with the rality of integral layers of different photosensitivity photosensitive layer 8 containing a different leuconitrile capable of dry processing.
    [Show full text]
  • Preparation and Properties of Alpha Nitrogen Derivatives of Furan. Henry Marvin Singleton Louisiana State University and Agricultural & Mechanical College
    Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1937 Preparation and Properties of Alpha Nitrogen Derivatives of Furan. Henry Marvin Singleton Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Part of the Chemistry Commons Recommended Citation Singleton, Henry Marvin, "Preparation and Properties of Alpha Nitrogen Derivatives of Furan." (1937). LSU Historical Dissertations and Theses. 7783. https://digitalcommons.lsu.edu/gradschool_disstheses/7783 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. PREPARATION AND PROPERTIES OF ALPHA NITROGEN DERIVATIVES OF FURAN A DISSERTATION SUBMITTED TO THE FACULTY . OF THE LOUISIANA STA-E UNIVERSITY AND AGRICULTURAL AND MECHANICaL COLLEGE IN PARTIAL FULFILLMENT OF TEE RE Q,U I RET TEN TS FOR THE DOCTOR OF FHILOSOPEY DEGREE UMI Number: DP69161 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. UMI Dissertation Publishing UMI DP69161 Published by ProQuest LLC (2015). Copyright in the Dissertation held by the Author. Microform Edition © ProQuest LLC. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code ProOuest ProQuest LLC.
    [Show full text]