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Sulfinyl Functional Group

Formula for the sulfoxide ; a chemical compound containing a sulfinyl functional group. RSOR' ( also known as oxidized sulfides). Sulfinyl Functional Group. (Yanti). (Helmenstine). 1. Naming. Names are formed by citing the prefix names for the groups R and R’

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Sulfinyl Functional Group

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  1. Formula for the sulfoxide ; a chemical compound containing a sulfinyl functional group. RSOR' ( also known as oxidized sulfides) Sulfinyl Functional Group (Yanti) (Helmenstine) 1

  2. Naming • Names are formed by citing the prefix names for the groups R and R’ • and in alphabetical order as separate words • followed by the class name "sulfoxide" or "sulfone", respectively • EXAMPLE: • When named as a sub group, use the prefix of the group • followed by sulfinyl or sulfonyl • and the name of the parent hydride corresponding to R • EXAMPLE: (ACD/Labs) 2a

  3. Naming continued (ACD/Labs) 2b

  4. 2c (ACD/Labs)

  5. Formula WritingR-S(=O)-R' 3a (ACD/Labs)

  6. Formula Writing continued Dimethyl Sulfoxide or methylsulfinylmethane (IUPAC Name) Draw the expanded structure below: Draw the condensed structure below: (PubChem) 3b

  7. Formula Writing Continued Dibromo sulfoxide;Sulfinyl dibromide Also known as sulfinyl bromide Sulfinyl dichloride, dichlorosulfoxide Also known as sulfinyl bromide SOBr2 or Br2OS SOCl2 or Cl2OS Fyi: The bivalent group SO is also called thionyl. Draw the expanded structures below: ( Stevenson 2477–2479) 3c

  8. Formula Writing Continued (CH3)2SO Dimethyl sulfoxide (DMSO) Draw the structure below: 2-amino-4-(methylsulfinyl)butanoic acid Finish Drawing the structure below: (Bedi) 3d

  9. Reactions ( Hunter 3368–3374) 4a

  10. Reactions Showing Intermediate Products At what point is a sulfoxide made? ( Hunter 3368–3374) 4b

  11. Preparations (Badia) (Silverman) http://www.chemistry.or.jp/journals/bcsj/J-STAGE/6910/pdf/69_2955.pdf (Ōae 72-80) 5a

  12. Natural Occurrences • An example of an sulfoxide occurring in nature is alliin in onions and garlic (Gama) 6a

  13. Garlic is known for its antibiotic capabilities. The first structure, alliin, is contained in garlic but has no antibiotic properties. When crushed, an enzyme (alinase) in the garlic comes in contact with "alliin" and removes the right half . Note: C=carbon, H=hydrogen, S=sulfur, O=oxygen. 6b (Costello)

  14. Sulfoxides and Other Species • Also found in blowflys and seaweed • It is not surprising to be found in marine products sulfur is the 6th most abundant element in seawater (Badia) 6c

  15. Human Uses and occurrences • Sulfoxides can be found in certain drugs such as esomeprazole and Armodafinil • Dimethyl sulfoxide (DMSO) can be derived from wood pulp • DMSO is produced through the normal decomposition of plants, as well as fresh and marine algae. • DMSO is found in small amounts in milk ("Dimethyl sulfoxide") 7a

  16. DMSO • Dissolves in both polar and nonpolar compounds • It has a distinctive property of penetrating the skin very readily, so that one may taste it soon after it comes into contact with the skin. Its taste has been described as oyster- or garlic-like. • Physicians use DMSO to carry other medicinal substances into the body quickly . • DMSO has been used for many years in sports medicine • It promotes healing of minor cuts and burns. (Badia) 7b

  17. Human Uses and occurrences • All of us knew that chopping onion makes our eyes weep. • Onions are part of the plant genus Allium along with garlic, chives, leeks and about 400 other cousins. • These vegetables absorb sulfur in the earth, which helps form a class of volatile organic molecules called amino acid sulfoxides. • These sulfoxides are the real tear-jerkers when onions go under the knife. 7c

  18. Human Uses and occurrences • Found that water soluble salts of sulfinyl dipropionic acids • Which are excellent replacements for polyphosphates in detergent compositions as ("Dimethyl sulfoxide") 7d

  19. Interesting Facts • DMSO can also be used for Cryoprotective Agents - Substances that provide protection against the harmful effects of freezing temperatures. • Omeprazole or Prilosec’s covering is a sulfoxide 5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1H-benzo[d]imidazole 8

  20. IR Spectra ("Spartan") • Spartan Ir Video • Web Ir ("Dimethyl sulfoxide") 9

  21. Spartan Electron Distribution Picture3C chain Video ("Spartan") 10

  22. Works Cited Advanced Chemistry Development, Inc. (ACD/Labs). ACD/ChemSketch Freeware, version 10.00, Advanced Chemistry Development, Inc., Toronto, ON, Canada, www.acdlabs.com, 2006 .http://www.acdlabs.com/iupac/nomenclature/93/r93_444.htm Badia, David. "A Computational Approach to Synthesis of Chiral Sullfoxides." 2006. University of Autonoma Barcolona, Web. 9 Mar 2010. <http://www.organic-chemPreparations>. Bedi PM,Mahajan MP,Kapoor VK (2004)Amidine derived 1,3-diazabuta-1,3-dienes as potential antibacterial and antifungal agents. Bioorganic & medicinal chemistry letters 14, 3821-4 (Source: ChEMBL) [PubMed:15203169] http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17016 re: Costello, Kwn. "CHECKING YOUR UNDERSTANDING OF PRESERVATION CHEMISTRY." Learning Chemistry Close to Home with Distant Learning. 09 14, 2006. Chemistryland, Web. 9 Mar 2010. <http://images.google.com/imgres?imgurl=http://www.chemistryland.com/CHM107/EarlyChemistry/PreservationChemistry/AlliinStart.jpg&imgrefurl=http://www.chemistryland.com/CHM107/EarlyChemistry/PreservationChemistry/PreservationChemistryQuestions.html&usg=__WzdjctVBeX1hnu6pCpqNd1wz9yU=&h=295&w=502&sz=41&hl=en&start=2&itbs=1&tbnid=5HzUwVeoSrwsqM:&tbnh=76&tbnw=130&prev=/images%3Fq%3Dalliin%26hl%3Den%26safe%3Dactive%26gbv%3D2%26tbs%3Disch:1>. "Dimethyl sulfoxide." Absolute Atronomy. SanFansisco: Free Software Foundation, Inc., 2008. Web. <http://www.absoluteastronomy.com/definition/Dimethyl_sulfoxide Gama, Ángeles, Lucía Z. Flores-López, Gerardo Aguirre, Miguel Parra-Hake, Lars H. Hellberg, and Ratnasamy Somanathan Oxidation of sulfides to chiral sulfoxides using Schiff base-vanadium (IV) complexesArkivoc MX-789E 2003. < http://www.search.com/reference/Sulfoxide> Helmenstine, Anne. "Sulfoxide Functional Group." About.com. 2010. New York Times, Web. 8 Mar 2010. <http://chemistry.about.com/od/organicchemistry/ig/Functional-Groups/Sulfoxide-Functional-Group.htm>. Hunter, W.H. "THE MECHANISM OF THE REDUCTION OF SULFONYL BROMIDES WITH PHOSPHORUS TRIBROMIDE1." J. Am. Chem. Soc., 54.8 (1932): 3368–3374. Web. 9 Mar 2010. <http://pubs.acs.org/doi/abs/10.1021/ja01347a053>. Ōae, Shigeru. Organic sulfur chemistry: structure and mechanism. illustrated. 1. Crc Press, 1991. 72-80. Print. PubChem, . "Dimethyl Sulfoxide - Compound Summary." PubChem. n.d. National Center for Biotechnology Information, Web. 9 Mar 2010. <http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=679>. Silverman, Richard. "Synthesis of sulfoxides." 2006. Organic Chemistry Portal, Web. 9 Mar 2010. <http://www.organic-chemistry.org/synthesis/C1S/sulfoxides.shtm>. "Spartan." Wavefunction. Web. 9 Mar 2010. <http://www.wavefun.com/products/spartan.html>. Stevenson, D. P. "The Structure of Thionyl Bromide." Journal of the American Chemical Society 62.9 (1940): 2477–2479. Web. 9 Mar 2010. <http://www.answers.com/topic/thionyl-bromide thionyl bromide >. Yanti, . "Benefits Onion Vegetable." Best Healthy Foods. 09 15 2009 . World Press, Web. 8 Mar 2010. <http://thebest-healthy-foods.com/onion-vegetable/>.

  23. Works Cited

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