Nomenclature (The Naming of Chemical Compounds)
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DNA Alkylation by Leinamycin Can Be Triggered by Cyanide and Phosphines
Bioorganic & Medicinal Chemistry Letters 11 (2001) 1511–1515 DNA Alkylation by Leinamycin Can Be Triggered by Cyanide and Phosphines Hong Zang, Leonid Breydo, Kaushik Mitra, Jeffrey Dannaldson and Kent S. Gates* Departments of Chemistry and Biochemistry, University of Missouri-Columbia, Columbia, MO 65211, USA Received 24 January 2001; accepted 14 March 2001 Abstract—Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (1) is potentiated by reaction of the antibiotic with thiols. Here, it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. Overall, the results suggest that reactions of cyanide and phosphines with leinamycin produce the oxathiolanone intermediate (2), which is known to undergo rearrangement to the DNA-alkylating episulfonium ion 4. # 2001 Elsevier Science Ltd. All rights reserved. Leinamycin (1) is a potent antitumor antibiotic that properties of the antibiotic. Here we report that phos- contains a unique 1,2-dithiolan-3-one 1-oxide hetero- phines and cyanide are able to trigger DNA alkylation cycle.1,2 Reaction of thiols with this sulfur heterocycle in by the antitumor antibiotic leinamycin. Results of our leinamycin initiates chemistry that leads to oxidative chemical model reactions and DNA-damage experi- DNA damage and DNA alkylation.3À6 Thiol-triggered ments suggest that reaction of cyanide and phosphines DNA alkylation by leinamycin involves initial conver- with leinamycin affords the critical oxathiolanone inter- sion of the parent antibiotic to the oxathiolanone form mediate (2), which subsequently undergoes rearrangement 2,5,7 followed by rearrangement to the episulfonium ion to the DNA-alkylating episulfonium ion 4. -
Brief Guide to the Nomenclature of Organic Chemistry
1 Brief Guide to the Nomenclature of Table 1: Components of the substitutive name Organic Chemistry (4S,5E)-4,6-dichlorohept-5-en-2-one for K.-H. Hellwich (Germany), R. M. Hartshorn (New Zealand), CH3 Cl O A. Yerin (Russia), T. Damhus (Denmark), A. T. Hutton (South 4 2 Africa). E-mail: [email protected] Sponsoring body: Cl 6 CH 5 3 IUPAC Division of Chemical Nomenclature and Structure suffix for principal hept(a) parent (heptane) one Representation. characteristic group en(e) unsaturation ending chloro substituent prefix 1 INTRODUCTION di multiplicative prefix S E stereodescriptors CHEMISTRY The universal adoption of an agreed nomenclature is a key tool for 2 4 5 6 locants ( ) enclosing marks efficient communication in the chemical sciences, in industry and Multiplicative prefixes (Table 2) are used when more than one for regulations associated with import/export or health and safety. fragment of a particular kind is present in a structure. Which kind of REPRESENTATION The International Union of Pure and Applied Chemistry (IUPAC) multiplicative prefix is used depends on the complexity of the provides recommendations on many aspects of nomenclature.1 The APPLIED corresponding fragment – e.g. trichloro, but tris(chloromethyl). basics of organic nomenclature are summarized here, and there are companion documents on the nomenclature of inorganic2 and Table 2: Multiplicative prefixes for simple/complicated entities polymer3 chemistry, with hyperlinks to original documents. An No. Simple Complicated No. Simple Complicated AND overall -
Naming Polyatomic Ions and Acids Oxyanions
Oxyanions Naming Polyatomic Ions and Oxyanions Acids Oxyanions- negative ions containing Oxyanions may contain the prefix oxygen. “hypo-”, less than, or “per-”, more than. These have the suffix “-ate” or “-ite” For example - “-ate” means it has more oxygen atoms ClO4 Perchlorate bonded, “-ite” has less - ClO3 Chlorate For example - ClO2 Chlorite 2- SO4 sulfate ClO- Hypochlorite 2- SO3 sulfite Acids Naming acids Naming Acids Certain compounds produce H+ ions in Does it contain oxygen? water, these are called acids. If it does not, it gets the prefix “hydro-” and If it does contain an oxyanion, then the suffix “-ic acid” replace the ending. You can recognize them because the neutral compound starts with “H”. HCl If the ending was “–ate”, add “-ic acid” Hydrochloric acid If the ending was “–ite”, add “-ous acid” For example HCl, H2SO4, and HNO3. HF Don’t confuse a polyatomic ion with a H2SO4 Sulfuric Acid Hydrofluoric acid neutral compound. H2SO3 Sulfurous Acid HCN HCO - is hydrogen carbonate, not an acid. 3 Hydrocyanic acid Examples Examples Nomenclature (naming) of Covalent compounds HNO3 HNO3 Nitric Acid HI HI Hydroiodic acid H3AsO4 H3AsO4 Arsenic Acid HClO2 HClO2 Chlorous Acid 1 Determining the type of bond Covalent bonding is very Covalent bonding is very First, determine if you have an ionic different from ionic naming compound or a covalent compound. similar to ionic naming A metal and a nonmetal will form an You always name the one that is least Ionic names ignored the subscript ionic bond. electronegative first (furthest from because there was only one possible Compounds with Polyatomic ions form fluorine) ratio of elements. -
Sodium and Specialty Cyanides Production Facility Nicholas A
University of Pennsylvania ScholarlyCommons Department of Chemical & Biomolecular Senior Design Reports (CBE) Engineering 4-20-2018 Sodium and Specialty Cyanides Production Facility Nicholas A. Baylis University of Pennsylvania, [email protected] Parth N. Desai University of Pennsylvania, [email protected] Kyle J. Kuhns University of Pennsylvania, [email protected] Follow this and additional works at: https://repository.upenn.edu/cbe_sdr Part of the Biochemical and Biomolecular Engineering Commons Baylis, Nicholas A.; Desai, Parth N.; and Kuhns, Kyle J., "Sodium and Specialty Cyanides Production Facility" (2018). Senior Design Reports (CBE). 101. https://repository.upenn.edu/cbe_sdr/101 This paper is posted at ScholarlyCommons. https://repository.upenn.edu/cbe_sdr/101 For more information, please contact [email protected]. Sodium and Specialty Cyanides Production Facility Abstract Sodium cyanide and specialty cyanide production are essential operations for various industrial processes, with primary applications in mining and mineral processing. Sodium cyanide, despite the high toxicity inherent in the material and its production process, is expected to grow 5% annually, with a projected global demand of 1.1 million tonnes in 2018. This report details a process design for producing sodium cyanide through the use of two intermediate reactions and successive downstream separations. The first major step is the production of hydrogen cyanide gas from ammonia and methane derived from natural gas, via the industry standard Andrussow reaction over a platinum-rhodium gauze catalyst. Aqueous sodium cyanide is produced via a neutralization reaction of absorbed hydrogen cyanide gas with aqueous sodium hydroxide. Downstream processes include the crystallization of solid sodium cyanide from the aqueous product, with the solid product being removed from slurry and brought to low-moisture content through a series of solid-liquid separations. -
Minutes of the IUPAC Chemical Nomenclature and Structure Representation Division (VIII) Committee Meeting Boston, MA, USA, August 18, 2002
Minutes of the IUPAC Chemical Nomenclature and Structure Representation Division (VIII) Committee Meeting Boston, MA, USA, August 18, 2002 Members Present: Dr Stephen Heller, Prof Herbert Kaesz, Prof Dr Alexander Lawson, Prof G. Jeffrey Leigh, Dr Alan McNaught (President), Dr. Gerard Moss, Prof Bruce Novak, Dr Warren Powell (Secretary), Dr William Town, Dr Antony Williams Members Absent: Dr. Michael Dennis, Prof Michael Hess National representatives Present: Prof Roberto de Barros Faria (Brazil) The second meeting of the Division Committee of the IUPAC Division of Chemical Nomenclature and Structure Representation held in the Great Republic Room of the Westin Hotel in Boston, Massachusetts, USA was convened by President Alan McNaught at 9:00 a.m. on Sunday, August 18, 2002. 1.0 President McNaught welcomed the members to this meeting in Boston and offered a special welcome to the National Representative from Brazil, Prof Roberto de Barros Faria. He also noted that Dr Michael Dennis and Prof Michael Hess were unable to be with us. Each of the attendees introduced himself and provided a brief bit of background information. Housekeeping details regarding breaks and lunch were announced and an invitation to a reception from the U. S. National Committee for IUPAC on Tuesday, August 20 was noted. 2.0 The agenda as circulated was approved with the addition of a report from Dr Moss on the activity on his website. 3.0 The minutes of the Division Committee Meeting in Cambridge, UK, January 25, 2002 as posted on the Webboard (http://www.rsc.org/IUPAC8/attachments/MinutesDivCommJan2002.rtf and http://www.rsc.org/IUPAC8/attachments/MinutesDivCommJan2002.pdf) were approved with the following corrections: 3.1 The name Dr Gerard Moss should be added to the members present listing. -
Acetate C2H3O2 Or CH3COO Or CH3CO2 Ammonium NH4
Name:_____________________ Memorization For AP Chem Polyatmic Ions AP Chemistry Polyatomic Ion list - - - Acetate C2H3O2 or CH 3COO or CH 3CO 2 + Ammonium NH 4 - Ammonium Carbonate NH 4CO 3 Cyanide CN - 2- Carbonate CO 3 2- Dichromate Cr 2O7 - Dihydrogen phosphate H2PO 4 - Hydrogen carbonate HCO 3 - Hydrogen sulfate HSO 4 - Hydronium H3O Hydroxide OH - 2- Monohydrogen Phosphate HPO 4 - Nitrate NO 3 - Nitrite NO 2 2- Oxalate C2O4 - Permanganate MnO 4 3- Phosphate PO 4 2- Sulfate SO 4 2- Sulfite SO 3 Hypochlorite ClO - - Chlorite ClO 2 - Chlorate ClO 3 - Perchlorate ClO 4 2- Chromate CrO 4 2- Silicate SiO 3 Thiocyanate SCN - 2- Thiosulfate S2O3 - Bromate BrO 3 2- Selenate SeO 4 - Bisulfite HSO 3 Name:_____________________ Memorization For AP Chem Rules for Naming an Acid When the name of the anion ends in –ide, the acid name begins with the prefix hydro-, the stem of the anion has the suffix –ic and it is followed by the word acid. -ide becomes hydro _____ic Acid Cl- is the Chloride ion so HCl = hydrochloric acid When the anion name ends in –ite, the acid name is the stem of the anion with the suffix –ous, followed by the word acid. -ite becomes ______ous Acid - ClO 2 is the Chlorite ion so HClO 2 = Chlorous acid. When the anion name ends in –ate, the acid name is the stem of the anion with the suffix –ic, followed by the word acid. -ate becomes ______ic Acid - ClO 3 is the Chlorate ion so HClO 3 = Chloric acid. Rules for Naming Ionic Compounds 1. -
A Low Temperature Structure of Nonane-1,9-Diaminium Chloride Chloroacetate: Hydroxyacetic Acid (1:1)
J Chem Crystallogr (2011) 41:703–707 DOI 10.1007/s10870-010-9957-6 ORIGINAL PAPER A Low Temperature Structure of Nonane-1,9-Diaminium Chloride Chloroacetate: Hydroxyacetic Acid (1:1) Agnieszka Paul • Maciej Kubicki Received: 24 February 2010 / Accepted: 31 December 2010 / Published online: 14 January 2011 Ó The Author(s) 2011. This article is published with open access at Springerlink.com Abstract The crystal structure of nonane-1,9-diaminium protons and to form salts with both, organic and inorganic chloride chloroacetate–hydroxyacetic acid (1:1) was deter- acids, together with a significant flexibility of the chain mined by X-ray diffraction at 100(1)K. The asymmetric fragment and tendency towards creation of the highly unit is composed of diaminium dication, chloroacetate and symmetric networks, can be used in so-called crystal chloride anions, and neutral hydroxyacetic acid molecule. engineering [2], i.e. in designing new materials with The aliphatic chain of 1,9-diamine is fully extended and it expected features. Such a predictable motifs in the crystal deviates only slightly from the perfect all-trans confor- structures, giving rise to a layer structure, were already mation. The two acidic residues are also nearly planar. The investigated in the series of hexane-1,6-diamine and layer structure is obtained as a consequence of hydrogen butane-1,4-diamine salts [3, 4]. bond interactions of a different lengths, with N–H and O–H Only five structures deposited in the Cambridge Struc- groups playing the role of donors and oxygen atoms and tural Database [5] (no multiple determinations, herein and chloride cations as acceptors. -
SAFETY DATA SHEET 1,9-Dibromo-Nonane-2,8-Dione According to Regulation (EC) No 1907/2006, Annex II, As Amended
Revision date: 03/01/2020 Revision: 1 SAFETY DATA SHEET 1,9-Dibromo-nonane-2,8-dione According to Regulation (EC) No 1907/2006, Annex II, as amended. Commission Regulation (EU) No 2015/830 of 28 May 2015. SECTION 1: Identification of the substance/mixture and of the company/undertaking 1.1. Product identifier Product name 1,9-Dibromo-nonane-2,8-dione Product number FD173289 CAS number 91492-76-1 1.2. Relevant identified uses of the substance or mixture and uses advised against Identified uses Laboratory reagent. Manufacture of substances. Research and development. 1.3. Details of the supplier of the safety data sheet Supplier Carbosynth Ltd 8&9 Old Station Business Park Compton Berkshire RG20 6NE UK +44 1635 578444 +44 1635 579444 [email protected] 1.4. Emergency telephone number Emergency telephone +44 7887 998634 SECTION 2: Hazards identification 2.1. Classification of the substance or mixture Classification (EC 1272/2008) Physical hazards Not Classified Health hazards Not Classified Environmental hazards Not Classified Additional information Caution. Not fully tested. 2.2. Label elements Hazard statements NC Not Classified 2.3. Other hazards No data available. SECTION 3: Composition/information on ingredients 3.1. Substances Product name 1,9-Dibromo-nonane-2,8-dione 1/8 Revision date: 03/01/2020 Revision: 1 1,9-Dibromo-nonane-2,8-dione CAS number 91492-76-1 Chemical formula C₉H₁₄Br₂O₂ SECTION 4: First aid measures 4.1. Description of first aid measures General information Get medical advice/attention if you feel unwell. Inhalation Remove person to fresh air and keep comfortable for breathing. -
9.7 Summary of Substitution and Elimination Reactions of Alkyl Halides 421
09_BRCLoudon_pgs4-3.qxd 11/26/08 12:25 PM Page 420 420 CHAPTER 9 • THE CHEMISTRY OF ALKYL HALIDES The occurrence of some inversion also shows that the lifetime of a tertiary carbocation is 8 very small. It takes about 10_ second for a chloride counterion to diffuse away from a carbo- cation and be replaced by solvent. The carbocations that undergo inversion do not last long enough for this process to take place. The competition of backside substitution (which gives inversion) with racemization shows that the lifetime of the carbocation is approximately in 8 this range. In other words, a typical tertiary carbocation exists for about 10_ second before it is consumed by its reaction with solvent. This very small lifetime provides a graphic illustration just how reactive carbocations are. PROBLEMS 9.27 The optically active alkyl halide in Eq. 9.61 reacts at 60 C in anhydrous methanol solvent to give a methyl ether A plus alkenes. The substitution reaction° is reported to occur with 66% racemization and 34% inversion. Give the structure of ether A and state how much of each enantiomer of A is formed. 9.28 In light of the ion-pair hypothesis, how would you expect the stereochemical outcome of an SN1 reaction (percent racemization and inversion) to differ from the result discussed in this section for an alkyl halide that gives a carbocation intermediate which is considerably (a) more stable or (b) less stable than the one involved in Eq. 9.61? E. Summary of the SN1 and E1 Reactions Let’s summarize the important characteristics of the SN1 and E1 reactions. -
Chapter 2: Alkanes Alkanes from Carbon and Hydrogen
Chapter 2: Alkanes Alkanes from Carbon and Hydrogen •Alkanes are carbon compounds that contain only single bonds. •The simplest alkanes are hydrocarbons – compounds that contain only carbon and hydrogen. •Hydrocarbons are used mainly as fuels, solvents and lubricants: H H H H H H H H H H H H C H C C H C C C C H H C C C C C H H H C C H H H H H H CH2 H CH3 H H H H CH3 # of carbons boiling point range Use 1-4 <20 °C fuel (gasses such as methane, propane, butane) 5-6 30-60 solvents (petroleum ether) 6-7 60-90 solvents (ligroin) 6-12 85-200 fuel (gasoline) 12-15 200-300 fuel (kerosene) 15-18 300-400 fuel (heating oil) 16-24 >400 lubricating oil, asphalt Hydrocarbons Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H C H eth- -ane ethane 2 6 H3C CH3 C3H8 prop- -ane propane C4H10 but- -ane butane C5H12 pent- -ane pentane C6H14 hex- -ane hexane C7H16 hept- -ane heptane C8H18 oct- -ane octane C9H20 non- -ane nonane C10H22 dec- -ane decane Hydrocarbons Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H H H C2H6 eth- -ane ethane H C C H H H H C H prop- -ane propane 3 8 H3C C CH3 or H H H C H 4 10 but- -ane butane H3C C C CH3 or H H H C H 4 10 but- -ane butane? H3C C CH3 or CH3 HydHrydorcocaarrbobnos ns Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H H H C2H6 eth- -ane ethane H C C H H H H C3H8 prop- -ane propane H3C C CH3 or H H H C H 4 10 but- -ane butane H3C C C CH3 or H H H C H 4 10 but- -ane iso-butane H3C C CH3 or CH3 HydHrydoroccarbrobnsons Formula Prefix Suffix Name Structure H H -
Introduction to Chemistry
Introduction to Chemistry Author: Tracy Poulsen Digital Proofer Supported by CK-12 Foundation CK-12 Foundation is a non-profit organization with a mission to reduce the cost of textbook Introduction to Chem... materials for the K-12 market both in the U.S. and worldwide. Using an open-content, web-based Authored by Tracy Poulsen collaborative model termed the “FlexBook,” CK-12 intends to pioneer the generation and 8.5" x 11.0" (21.59 x 27.94 cm) distribution of high-quality educational content that will serve both as core text as well as provide Black & White on White paper an adaptive environment for learning. 250 pages ISBN-13: 9781478298601 Copyright © 2010, CK-12 Foundation, www.ck12.org ISBN-10: 147829860X Except as otherwise noted, all CK-12 Content (including CK-12 Curriculum Material) is made Please carefully review your Digital Proof download for formatting, available to Users in accordance with the Creative Commons Attribution/Non-Commercial/Share grammar, and design issues that may need to be corrected. Alike 3.0 Unported (CC-by-NC-SA) License (http://creativecommons.org/licenses/by-nc- sa/3.0/), as amended and updated by Creative Commons from time to time (the “CC License”), We recommend that you review your book three times, with each time focusing on a different aspect. which is incorporated herein by this reference. Specific details can be found at http://about.ck12.org/terms. Check the format, including headers, footers, page 1 numbers, spacing, table of contents, and index. 2 Review any images or graphics and captions if applicable. -
United States Patent Office Patented Jan
3,071,593 United States Patent Office Patented Jan. 1, 1963 2 3,071,593 O PREPARATION OF AELKENE SULFES Paul F. Warner, Philips, Tex., assignor to Philips Petroleum Company, a corporation of Delaware wherein each R is selected from the group consisting of No Drawing. Filed July 27, 1959, Ser. No. 829,518 5 hydrogen, alkyl, aryl, alkaryl, aralkyl and cycloalkyl 8 Claims. (C. 260-327) groups having 1 to 8 carbon atoms, the combined R groups having up to 12 carbon atoms. Examples of Suit This invention relates to a method of preparing alkene able compounds are ethylene oxide, propylene oxide, iso sulfides. Another aspect relates to a method of convert butylene oxide, a-amylene oxide, styrene oxide, isopropyl ing an alkene oxide to the corresponding sulfide at rela O ethylene oxide, methylethylethylene oxide, 3-phenyl-1, tively high yields without refrigeration. 2-propylene oxide, (3-methylphenyl) ethylene oxide, By the term "alkene sulfide' as used in this specifica cyclohexylethylene oxide, 1-phenyl-3,4-epoxyhexane, and tion and in the claims, I mean to include not only un the like. substituted alkene sulfides such as ethylene sulfide, propyl The salts of thiocyanic acid which I prefer to use are ene sulfide, isobutylene sulfide, and the like, but also 5 the salts of the alkali metals or ammonium. I especially hydrocarbon-substituted alkene sulfides such as styrene prefer ammonium thiocyanate, sodium thiocyanate, and oxide, and in general all compounds conforming to the potassium thiocyanate. These compounds can be reacted formula with ethylene oxide in a cycloparaffin diluent to produce 20 substantial yields of ethylene sulfide and with little or S no polymer formation.