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The Synthesis and Characterization of Novel Pentafluorosulfanyl-Containing Heterocycles and Pentafluorosulfanyldifluoromethane
Clemson University TigerPrints All Dissertations Dissertations May 2019 The yS nthesis and Characterization of Novel Pentafluorosulfanyl-Containing Heterocycles and Pentafluorosulfanyldifluoromethane Steven Paul Belina Clemson University, [email protected] Follow this and additional works at: https://tigerprints.clemson.edu/all_dissertations Recommended Citation Belina, Steven Paul, "The yS nthesis and Characterization of Novel Pentafluorosulfanyl-Containing Heterocycles and Pentafluorosulfanyldifluoromethane" (2019). All Dissertations. 2373. https://tigerprints.clemson.edu/all_dissertations/2373 This Dissertation is brought to you for free and open access by the Dissertations at TigerPrints. It has been accepted for inclusion in All Dissertations by an authorized administrator of TigerPrints. For more information, please contact [email protected]. THE SYNTHESIS AND CHARACTERIZATION OF NOVEL PENTAFLUOROSULFANYL-CONTAINING HETEROCYCLES AND PENTAFLUOROSULFANYLDIFLUOROMETHANE A Dissertation Presented to the Graduate School of Clemson University In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy Chemistry by Steven Paul Belina May 2019 Accepted by Joseph S. Thrasher, Ph.D., Committee Chair Julia L. Brumaghim, Ph.D. R. Karl Dieter, Ph.D. Joseph W. Kolis, Ph.D. Title Page ABSTRACT Beginning in the early 1960s, scientists began to experiment with the pentafluorosulfanyl moiety. The unique properties of the functional group has attracted interest among fluorine chemists and more recently even organic chemists. These properties include high group electronegativity, high steric bulk, high lipophilicity, a highly electron withdrawing nature, and a square pyramidal geometry. However, the development and deployment of the pentafluorosulfanyl functional group has been significantly slowed. The main cause for the slow development is a lack of easily available reagents to synthesize pentafluorosulfanyl-containing compounds. Historically, the primary reagents used for synthesizing pentafluorosulfanyl-containing compounds were SF5Cl and SF5Br. -
United States Patent As Fice Patiented Sept
s 2,904,403 United States Patent As fice Patiented Sept. 15, 1959 1 2 are agitated during this period by any suitable means. The vessel is then cooled, opened and iodine penta 2,904,403 fluoride collected and purified by conventional procedures such as distillation. When alkali or alkaline earth metal PREPARATION OF BF iodates are used in the process, the iodine pentafluoride William Channing Smith, Wilmington, Del, assignor to may be isolated in the form of a solid complex compound E. H. du Pont de Nemours and Company, Wilmington, with alkali or alkaline earth metal fluorides. Dei, a corporation of Delaware in a continuous process gaseous sulfur tetrafluoride is No Drawing. Application June 7, 1957 passed through a tube containing the iodine compound, Serial No. 664,162 0 preferably heated to a temperature high enough to vola tilize the iodine pentafluoride as it is formed. The 5 Claims. (C. 23-205) iodine pentafluoride is separated from the gas effluent by cooling in traps and the unreacted sulfur tetrafluoride is recycled through the reaction tube. This invention relates to iodine fluorides and has as 5 The following examples illustrate the process of the its primary object provision of a novel method of prepar invention. ing such fluorides, iodine pentafluoride in particular. Iodine pentafluoride is a versatile and well-known Example 1 fluorinating agent which can be used to prepare fluorine (A) A bomb, lined with stainless steel and of 145 mi. bearing compounds that are not readily accessible by 20 capacity, was charged with 33.4 g. (0.10 mode) of iodine other routes. -
United States Patent Office Patented Mar
3,373,000 United States Patent Office Patented Mar. 2, 1968 2 3,373,000 monofluoride is also an economical reactant, since it is PROCESS FOR PREPARING TETRAFLUORDES conveniently prepared by the disproportionation of ele AND HEXAFLUOR DES mental chlorine in liquid hydrogen fluoride, thereby avoid James J. Pitts, West Haven, and Albert W. Jache, North ing the use of expensive elemental fluorine. The selective Haven, Conn., assignors to Olin Mathieson Chemical fluorination process of this invention is particularly Sur Corporation, a corporation of Virginia prising and unexpected in view of the prior art which No Drawing. Filed Nov. 1, 1966, Ser. No. 591,079 teaches that chlorine monofluoride adds to a wide variety 9 Claims. (Cl. 23-352) of compounds, thereby acting as a chloro-fluorinating agent. For instance, U.S. Patent 3,035,893 discloses the 10 preparation of sulfur chloride pentafluoride from Sulfur ABSTRACT OF THE DISCLOSURE tetrafluoride and chlorine monofluoride. The tetrafluorides and hexafluorides of sulfur, selenium According to the process of this invention, the tetra and tellurium are provided by reacting chlorine mono fluorides and hexafluorides of sulfur, selenium and tel fluoride with sulfur, selenium, tellurium, metal sulfides, lurium are provided by reacting chlorine monofluoride metal selenides or metal tellurides. The hexafluorides of 15 with a material selected from the group consisting of Sul tungsten, molybdenum and uranium are provided by the fur, selenium, tellurium, metal sulfides, metal selenides reaction of chlorine monofluoride with the metals, their and metal tellurides. The hexafluorides of tungsten, oxides, sulfides and salts containing the metallate anion. molybdenum and uranium are provided by reacting These tetrafluorides and hexafluorides are well-known chlorine monofluoride with a material selected from the compounds, useful as fluorinating agents, gaseous di 20 group consisting of tungsten; molybdenum, uranium; the electrics, sources of high purity metallic powders, etc. -
Chemical Names and CAS Numbers Final
Chemical Abstract Chemical Formula Chemical Name Service (CAS) Number C3H8O 1‐propanol C4H7BrO2 2‐bromobutyric acid 80‐58‐0 GeH3COOH 2‐germaacetic acid C4H10 2‐methylpropane 75‐28‐5 C3H8O 2‐propanol 67‐63‐0 C6H10O3 4‐acetylbutyric acid 448671 C4H7BrO2 4‐bromobutyric acid 2623‐87‐2 CH3CHO acetaldehyde CH3CONH2 acetamide C8H9NO2 acetaminophen 103‐90‐2 − C2H3O2 acetate ion − CH3COO acetate ion C2H4O2 acetic acid 64‐19‐7 CH3COOH acetic acid (CH3)2CO acetone CH3COCl acetyl chloride C2H2 acetylene 74‐86‐2 HCCH acetylene C9H8O4 acetylsalicylic acid 50‐78‐2 H2C(CH)CN acrylonitrile C3H7NO2 Ala C3H7NO2 alanine 56‐41‐7 NaAlSi3O3 albite AlSb aluminium antimonide 25152‐52‐7 AlAs aluminium arsenide 22831‐42‐1 AlBO2 aluminium borate 61279‐70‐7 AlBO aluminium boron oxide 12041‐48‐4 AlBr3 aluminium bromide 7727‐15‐3 AlBr3•6H2O aluminium bromide hexahydrate 2149397 AlCl4Cs aluminium caesium tetrachloride 17992‐03‐9 AlCl3 aluminium chloride (anhydrous) 7446‐70‐0 AlCl3•6H2O aluminium chloride hexahydrate 7784‐13‐6 AlClO aluminium chloride oxide 13596‐11‐7 AlB2 aluminium diboride 12041‐50‐8 AlF2 aluminium difluoride 13569‐23‐8 AlF2O aluminium difluoride oxide 38344‐66‐0 AlB12 aluminium dodecaboride 12041‐54‐2 Al2F6 aluminium fluoride 17949‐86‐9 AlF3 aluminium fluoride 7784‐18‐1 Al(CHO2)3 aluminium formate 7360‐53‐4 1 of 75 Chemical Abstract Chemical Formula Chemical Name Service (CAS) Number Al(OH)3 aluminium hydroxide 21645‐51‐2 Al2I6 aluminium iodide 18898‐35‐6 AlI3 aluminium iodide 7784‐23‐8 AlBr aluminium monobromide 22359‐97‐3 AlCl aluminium monochloride -
Sulfur Dioxide and “Sulfurous Acid” Solutions. S + O 2 → SO2 (G
Sulfur Dioxide and “Sulfurous Acid” Solutions. S + O2 → SO2 (g) Structure: sp2 at sulfur, two used for σ bonds, one for lone pair. : δ+ S - δ- δ O O Liquid SO2: Easy to get (bp = -10 °C) and easy to keep liquid at room T under slight pressure. It is quite a good solvent; SO2 is a polar molecule, and the liquid is associated by dipole-dipole attraction. Dissolves polar molecules and ionic compounds, and easy to remove by evaporation. Aqueous solutions: SO2 is soluble in water. Most of it stays in the form of hydrogen bonded “hydrate” (see CO2). At equilibrium in neutral water (no added base) a small portion of it reacts: - H+ - H+ - 2- SO2 (aq) + H2O HO-SO2 SO3 (sulfite - pyramidal) + H+ + H+ - H-SO3 (bisulfite) - 2- 2- Also, 2 HSO3 S2O5 + H2O (structure = [O2S-SO3] ) Many salts of all these anions are known. Complexes formed with sulfite ion and SO2 itself. Sulfur Trioxide and Sulfuric Acid. 2 SO2 + O2 → 2 SO3 (g) Condenses to a liquid at room T, liquid contains monomer and trimer. O O S O O O O O S S S O O O O O Also get solid polymers. SO3 is a powerful oxidant, with water, gives sulfuric acid – H2SO4. A viscous, hydrogen bonded liquid; which is a good strongly acidic solvent. In dilute solutions in water it is a dibasic acid. - H+ - H+ - 2- H2SO4 (aq) HSO4 (bisulfate) SO4 (sulfate) + H+ + H+ Many salts known for both anions. Sulfate can be monodentate or bidentate ligand. SO3 dissolves in concentrated H2SO4 to give “fuming” sulfuric acid which contains some pyrosulfuric acid – VERY CORROSIVE H2SO4 + SO3 H2S2O7 Halides of Sulfur Sulfur hexafluoride (SF6) is a gas a stp. -
Theoretical Bonding Description of Alkylidene Chalcogen (O, S, Se) Difluorides
Inorg. Chem. 1999, 38, 6257-6260 6257 Theoretical Bonding Description of Alkylidene Chalcogen (O, S, Se) Difluorides (H2CdXF2): Planar versus Bent Conformations J. A. Dobado, Henar Martı´nez-Garcı´a, and Jose´ Molina Molina* Grupo de Modelizacio´n y Disen˜o Molecular, Instituto de Biotecnologı´a, Campus Fuentenueva, Universidad de Granada, 18071-Granada, Spain ReceiVed June 23, 1999 Theoretical descriptions of alkylidene chalcogen difluorides have been performed on their planar (1-3) and bent (4-6) conformations. The planar T-shaped conformations were the most stable ones, from the calculations performed (Gaussian-G2 and B3LYP/6-311+G*). The bonding nature of the T-shaped (C2V) structures has also been analyzed by means of the atoms in molecules (AIM) theory and electron localization function analyses. Introduction HF calculations warrant further investigation on the potential The bonding nature of pnicogen and chalcogen ylides has energy surface for these structures, including a detailed descrip- been controversial for years, and recently Gilheany1 has tion of the bonding nature. This theoretical bonding description reviewed the chemical bonding in phosphine ylides. In this should include the electron correlation effects due to the nature - - context, our laboratory has performed calculations on pnicogen2 of the F S F moiety. and chalcogen3 oxides and sulfides, and very recently a general In this paper we present theoretical evidence for the stability study on pnicogen and chalcogen ylides has been presented.4 of planar T-shaped (C2V) alkylidene chalcogen difluorides Alkylidene chalcogen difluorides present special bonding together with the topology characterization of the electron charge F properties, and the sulfur derivatives were first synthesized by density, (r), and the electron localization function (ELF). -
Exemption for the Use of Cadmium in Portable Batteries and Accumulators
Exemption for the use of cadmium in portable batteries and accumulators intended for the use in cordless power tools in the context of the Batteries Directive 2006/66/EC Final Report (revised) 26 January 2010 Consortium ESWI Expert TeamBIPRO, to S upportUmweltbundesamt Waste Implementation BiPRO Beratungsgesellschaft für integrierte Problemlösungen ENV.G.4/FRA/2007/0066 iii European Commission ESWI Final Report - Replacement of Cadmium Batteries in Cordless Power Tools ENV.G.4/FRA/2007/0066 iv Executive Summary Background The Batteries Directive 2006/66/EC (repealing Directive 91/157/EEC) entered into force on 26 September 20061. The Directive sets out rules applicable to all batteries and accumulators that are put on the European Union market. These rules include, among others, restriction on the use of cadmium in portable batteries and accumulators (PBA) according to Article 4(1)(b) of the Directive. Portable batteries and accumulators, including those incorporated into appliances, that contain more than 0,002% of cadmium by weight shall not be placed on the market. However, according to Article 4(3) of the Directive the above requirement shall not apply to portable batteries and accumulators intended for use in: (a) emergency and alarm systems, including emergency lighting; (b) medical equipment; or (c) cordless power tools. Furthermore, based on Article 4(4) of the Directive the Commission shall review the exemption from the cadmium ban for use in cordless power tool with a view to the prohibition of cadmium in batteries and accumulators. The Commission shall submit a corresponding report to the European Parliament and to the Council by 26 September 2010, together, if appropriate, with relevant proposals. -
TIH/PIH List
Hazardous Materials Designated as TIH/PIH (consolidated AAR and Railinc lists) 3/12/2007 STCC Proper Shipping Name 4921402 2-CHLOROETHANAL 4921495 2-METHYL-2-HEPTANETHIOL 4921741 3,5-DICHLORO-2,4,6-TRIFLUOROPYRIDINE 4921401 ACETONE CYANOHYDRIN, STABILIZED 4927007 ACROLEIN, STABILIZED 4921019 ALLYL ALCOHOL 4923113 ALLYL CHLOROFORMATE 4921004 ALLYLAMINE 4904211 AMMONIA SOLUTION 4920360 AMMONIA SOLUTIONS 4904209 AMMONIA, ANHYDROUS 4904210 AMMONIA, ANHYDROUS 4904879 AMMONIA, ANHYDROUS 4920359 AMMONIA, ANHYDROUS 4923209 ARSENIC TRICHLORIDE 4920135 ARSINE 4932010 BORON TRIBROMIDE 4920349 BORON TRICHLORIDE 4920522 BORON TRIFLUORIDE 4936110 BROMINE 4920715 BROMINE CHLORIDE 4918505 BROMINE PENTAFLUORIDE 4936106 BROMINE SOLUTIONS 4918507 BROMINE TRIFLUORIDE 4921727 BROMOACETONE 4920343 CARBON MONOXIDE AND HYDROGEN MIXTURE, COMPRESSED 4920399 CARBON MONOXIDE, COMPRESSED 4920511 CARBON MONOXIDE, REFRIGERATED LIQUID 4920559 CARBONYL FLUORIDE 4920351 CARBONYL SULFIDE 4920523 CHLORINE 4920189 CHLORINE PENTAFLUORIDE 4920352 CHLORINE TRIFLUORIDE 4921558 CHLOROACETONE, STABILIZED 4921009 CHLOROACETONITRILE 4923117 CHLOROACETYL CHLORIDE 4921414 CHLOROPICRIN 4920516 CHLOROPICRIN AND METHYL BROMIDE MIXTURES 4920547 CHLOROPICRIN AND METHYL BROMIDE MIXTURES 4920392 CHLOROPICRIN AND METHYL CHLORIDE MIXTURES 4921746 CHLOROPIVALOYL CHLORIDE 4930204 CHLOROSULFONIC ACID 4920527 COAL GAS, COMPRESSED 4920102 COMMPRESSED GAS, TOXIC, FLAMMABLE, CORROSIVE, N.O.S. 4920303 COMMPRESSED GAS, TOXIC, FLAMMABLE, CORROSIVE, N.O.S. 4920304 COMMPRESSED GAS, TOXIC, FLAMMABLE, CORROSIVE, N.O.S. 4920305 COMMPRESSED GAS, TOXIC, FLAMMABLE, CORROSIVE, N.O.S. 4920101 COMPRESSED GAS, TOXIC, CORROSIVE, N.O.S. 4920300 COMPRESSED GAS, TOXIC, CORROSIVE, N.O.S. 4920301 COMPRESSED GAS, TOXIC, CORROSIVE, N.O.S. 4920324 COMPRESSED GAS, TOXIC, CORROSIVE, N.O.S. 4920331 COMPRESSED GAS, TOXIC, CORROSIVE, N.O.S. 4920165 COMPRESSED GAS, TOXIC, FLAMMABLE, N.O.S. 4920378 COMPRESSED GAS, TOXIC, FLAMMABLE, N.O.S. 4920379 COMPRESSED GAS, TOXIC, FLAMMABLE, N.O.S. -
Working with Hazardous Chemicals
A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training in experimental organic chemistry. All hazardous materials should be handled using the standard procedures for work with chemicals described in references such as "Prudent Practices in the Laboratory" (The National Academies Press, Washington, D.C., 2011; the full text can be accessed free of charge at http://www.nap.edu/catalog.php?record_id=12654). All chemical waste should be disposed of in accordance with local regulations. For general guidelines for the management of chemical waste, see Chapter 8 of Prudent Practices. In some articles in Organic Syntheses, chemical-specific hazards are highlighted in red “Caution Notes” within a procedure. It is important to recognize that the absence of a caution note does not imply that no significant hazards are associated with the chemicals involved in that procedure. Prior to performing a reaction, a thorough risk assessment should be carried out that includes a review of the potential hazards associated with each chemical and experimental operation on the scale that is planned for the procedure. Guidelines for carrying out a risk assessment and for analyzing the hazards associated with chemicals can be found in Chapter 4 of Prudent Practices. The procedures described in Organic Syntheses are provided as published and are conducted at one's own risk. Organic Syntheses, Inc., its Editors, and its Board of Directors do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. -
Substances of Concern List
< KUBOTA Group Green Procurement Guidelines Appendix > April 2009 Established April 2010 Revised to Ver.2 April 2011 Revised to Ver.3 Substances of Concern List April 2011 KUBOTA Corporation Introduction This document is for providing information related to "3. Substances of Concern" of "Eco-friendliness standards for products" specified in "KUBOTA Group Green Procurement Guidelines" revised on April 2011. Table of Contents Number of Substances Table Number, Definition of Substances Page or Substance Groups Table 1 : Substances to be Prohibited Substances to be Prohibited means the substances which should not be 144 p3 contained in the products nor used in the production process. Table 2 : Substances to be Restricted Substances to be Restricted means the substances which should not be contained in the products nor used in the production process under the certain 7p6 conditions or applications. They are to be reduced gradually the content and use with the time limit and the target and to be promoted the substitution. Attached Table I-A : RoHS Exemptions List - p9 Attached Table I-B : ELV Exemptions List - p13 Table 3 : Substances to be Controlled Substances to be Controlled means the substances which should be recognized - p16 their presence in the products or use in the production process from the viewpoint of the environmental impact of the products life cycle. Reference List of Substances to be Prohibited, Restricted and Controlled Reference List of Substances to be Prohibited, Restricted and Controlled 4272 p17 exemplifies Substances to be Prohibited, Substances to be Restricted and Substances to be Controlled. Disclaimer While the information is made based on the related regulatory control etc. -
Supplementary Information Cocrystal Design by Network-Based Link Prediction
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is © The Royal Society of Chemistry 2019 Supplementary Information Cocrystal design by network-based link prediction Jan-Joris Devogelaer, Sander J.T. Brugman, Hugo Meekes, Paul Tinnemans, Elias Vlieg, René de Gelder Table of Contents S1 Materials and syntheses page 1 S2 Single-crystal X-ray structure determinations, ORTEP plots and H-Bonding page 6 a) CCDC 1940959 = p1812d: 4,4’-bipyridine + resorcinol b) CCDC 1940950 = p1823c: 1,2-di(4-pyridyl)ethylene + 4-aminobenzoic acid c) CCDC 1940956 = p1823a: 1,2-di(4-pyridyl)ethylene + 4-aminobenzoic acid dihydrate d) CCDC 1940954 = p1907a: 1,2-di(4-pyridyl)ethylene + sebacic acid e) CCDC 1940949 = p1818a: 4,4’-bipyridine + suberic acid f) CCDC 1940953 = p1922b: 1,2-di(4-pyridyl)ethylene + oxalic acid g) CCDC 1940955 = p1914b: 1,2-di(4-pyridyl)ethylene + oxalic acid dihydrate i) CCDC 1940951 = p1908a: 1,2-bis(4-pyridyl)ethane + salicylic acid j) CCDC 1940958 = p1926b: 1,2-di(4-pyridyl)ethylene + 4-nitrobenzoic acid k) CCDC 1940952 = p1910a: 1,2-di(4-pyridyl)ethylene + phthalic acid l) CCDC 1940957 = p1913a: 1,2-di(4-pyridyl)ethylene + malonic acid S3 Top 100 predictions of the scoring method page 17 S4 Predefined lists of common solvents and gases page 21 S1 - Materials and syntheses We first present the materials in Table S1, after which we discuss the protocol used to obtain crystals suitable for single-crystal X-ray diffraction. Besides the two-component structures shown in Table 2, an additional cocrystal dihydrate (c) and salt dihydrate (g) were found. -
Facts on File DICTIONARY of INORGANIC CHEMISTRY
The Facts On File DICTIONARY of INORGANIC CHEMISTRY The Facts On File DICTIONARY of INORGANIC CHEMISTRY Edited by John Daintith ® The Facts On File Dictionary of Inorganic Chemistry Copyright © 2004 by Market House Books Ltd All rights reserved. No part of this book may be reproduced or utilized in any form or by any means, electronic or mechanical, including photocopying, recording, or by any information storage or retrieval systems, without permission in writing from the publisher. For information contact: Facts On File, Inc. 132 West 31st Street New York NY 10001 Library of Congress Cataloging-in-Publication Data The Facts on File dictionary of inorganic chemistry / edited by John Daintith. p. cm. Includes bibliographical references. ISBN 0-8160-4926-2 (alk. paper). 1. Chemistry—Dictionaries. I. Title: Dictionary of inorganic chemistry. II. Daintith, John. XXXXXXXXX XXXXXXXXX XXXXXXXXXX Facts On File books are available at special discounts when purchased in bulk quantities for businesses, associations, institutions, or sales promotions. Please call our Special Sales Department in New York at (212) 967-8800 or (800) 322-8755. You can find Facts On File on the World Wide Web at http://www.factsonfile.com Compiled and typeset by Market House Books Ltd, Aylesbury, UK Printed in the United States of America MP 10987654321 This book is printed on acid-free paper CONTENTS Preface vii Entries A to Z 1 Appendixes I. The Periodic Table 244 II. The Chemical Elements 245 III. The Greek Alphabet 247 IV. Fundamental Constants 247 V. Webpages 248 Bibliography 248 PREFACE This dictionary is one of a series covering the terminology and concepts used in important branches of science.