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Discover New IUPAC Organic Nomenclature with ACD/Name Discover New IUPAC Organic Nomenclature with ACD/Name Andrey Yerin and all ACD/Labs team developing and supporting nomenclature tools ACS 248th National Meeting ACD/Labs Workshop San Francisco, USA, August 11, 2014 The Scope of this Workshop Proliferation of chemical names New IUPAC recommendations The concept of preferred IUPAC name (PIN) What is changed? Most principle cases. How do we implement new rules? The degree of changes Are we ready to release a new software version? The quality of chemical names Generate and check! Two ACD/Name related presentations already delivered: CINF. New IUPAC Organic Nomenclature: from bottle label to database update CHED. Teaching and learning of multilingual chemical nomenclature with ACD/Name This presentation incorporates some parts of these presentations and includes specific examples of changes in organic nomenclature. Proliferation of Names A chemical name is created according to nomenclature rules; most commonly according to IUPAC rules. But there are too many rules! Several systematic names are possible for this structure -Butyrolactone Dihydro-2(3H)-furanone Dihydrofuran-2(3H)-one 4-Hydroxybutanoic acid lactone O 1-Oxacyclopentan-2-one O Oxolan-2-one 2-Oxotetrahydrofuran Tetrahydro-2-furanon All of these names correctly describe the structure. But the multiplicity of systematic names is inconvenient and diminishes the role of nomenclature. IUPAC Nomenclature The development of chemical nomenclature is governed by International Union of Pure and Applied Chemistry (IUPAC). Division of Chemical Nomenclature and Structure www.iupac.org Representation (Division VIII) All specific IUPAC recommendations are published in Journal of Pure and Applied Chemistry and freely available. A collection of main recommendations can be found at www.chem.qmul.ac.uk/iupac hosted by School of Biological and Chemical Sciences, Queen Mary University of London. In additional to specific recommendations IUPAC publishes books for all areas of chemical nomenclature. The books can be purchased but after some period the content can be available free of charge. Is there a “most systematic” name? The nice thing about standards is, there are so many to choose from C. Northcote Parkinson … the rules of systematic nomenclature need not necessarily lead to a unique name for each compound… To force the naming of all compounds into the Procrustean bed of one set of rules would not serve the needs of general communication. A Guide to IUPAC Nomenclature of Organic Compounds, 1993 To enforce the role of systematic nomenclature the need of having one best name has been recognized by IUPAC: …we have developed rules for assigning ‘preferred IUPAC names’, while continuing to allow alternative names in order to preserve the diversity and adaptability of the nomenclature… Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013 New IUPAC Organic Nomenclature In December 2013, the book “Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names” was published. It is truly a long awaited publication. The work started in 1992. The IUPAC project was initiated in 2001. This major organic nomenclature publication is an answer to the rapid development of chemistry and appearance of new classes of chemicals we have seen over the past 20 years. The book deals with naming principles that were unchanged for about 35 years since the IUPAC Blue book was published in 1979. New IUPAC Organic Nomenclature IUPAC was not silent all these years. While “A Guide to IUPAC nomenclature of organic chemistry” 1993 did not include the criteria, it explained the principles and included some first hints of preferred names. Between 1979 and 2013 several important recommendations related to specific classes have appeared: Von Baeyer polycyclic systems (1999) Extension and revision of nomenclature for spiro compounds (1999) Used and bridged-fused (1998) Phane nomenclature (1998, 2002) Natural products and related compounds (1999) Recommendations on fullerene nomenclature (2002, 2005) Other publications The book incorporates all nomenclature development for the last 35 years and introduces many new procedures. New IUPAC Organic Nomenclature Practically all of the work was done by two authors – Henri Favre and Warren Powell, but many people participated in all stages. It is important to note that the book was reviewed not only by classical nomenclature experts but experts in computerized nomenclature as well. The experts from ACD/Labs, CambridgeSoft and NextMove Software were involved. The most principle innovation is the concept of preferred IUPAC name (PIN) selected by hierarchical sets of criteria. There are many other changes compared to the Blue Book 1979. It takes ten pages just to list them. Lets see what ACD/Name provides for naming. ACD/Name is Simple to Use but Advanced Just draw a structure and push the button to get the chemical name. Names can be generated for most classes of organic compounds in full accordance with IUPAC recommendations. ACD/Name Tools IUPAC numbering can be shown. The display of numbering scheme allows you to understand the locants for substituents and functional groups. ACD/Name Tools Name fragments are associated with the structure fragments. Pointing at any part of a name or structure allows you to understand the structure to name relationship. ACD/Name Tools Name segments are explained with the corresponding IUPAC rules. Name segments are classified by their role in chemical names. ACD/Name Tools Full text of IUPAC recommendations is provided. The links allow you to access any specific rule defining the naming principles for specific segments. ACD/Name Tools Stereodescriptors are generated and explained. An assignment of each stereodescriptor is explained with a hierarchical graph to conclude the seniority of ligands. ACD/Name Tools Supports not only most classes of organic compounds but biochemicals and some inorganic compounds also. Thus, being powerful for scientific and industrial use, the program retains high value for all levels of chemical education. New IUPAC Organic Nomenclature The new Blue Book introduced many changes; the most significant of which include: Less trivial names Length is senior to unsaturation More locants More enclosing marks Multiplication over substitution Al, Ga, In and Tl are now ‘organic elements’ many other specific changes Of high importance is the fact that the number of criteria to select the best name has increased significantly. The nomenclature became more systematic but at the same time more difficult for humans. New IUPAC Organic Nomenclature The systematic nomenclature assumes general naming principles and minimal number of trivial names. Such nomenclature is easier to learn and implement in software. The downside is that some very common names are changed. Was tetrahydrofuran PIN oxolane O Tetrahydrofuran is still acceptable! Some people would like to make it the preferred name, but we must agree to disagree. Are there anybody who would argue with this change? Was tetrahydro-2H-pyran PIN oxane O New IUPAC Organic Nomenclature You can see these changes for the following example. New name is very simple as compared to the old name. Why Wait to Program Our Software? The first public draft of the new Blue Book was made available in 2004. Some producers of naming software decided to implement new principles and claimed compatibility to ‘2004 rules’. Being involved in the development of IUPAC recommendations, ACD/Labs decided to wait until later versions, keeping in mind that several principle procedures were still under consideration well before the actual publication. We did implement some earlier well-agreed upon changes, including the change of seniority of chain length to degree of unsaturation. Was 2-ethylbut-1-ene H C C H 3 3 PIN 3-methylidenepentane C H 2 It means that changes concern not only advanced cases but some very simple cases as well. Note that new name corresponds to CAS naming principles. New IUPAC Organic Nomenclature Chain length is senior to unsaturation. Old name was 2-heptylbuta-1,3-diene. New IUPAC Organic Nomenclature Cycles are now senior to chains for the same atom content. Old rules had no specific criterion but “larger parent” was favored 1-cyclopropyldodecane. New IUPAC Organic Nomenclature Multiplication is senior to substitution. Sometimes old name was easier to construct. New IUPAC Organic Nomenclature Al, Ga, In and Tl substances are named now as organic compounds. Previously were named as organometallic compounds. New IUPAC Organic Nomenclature Many previously omitted locants are now cited to avoid ambiguity. Ambiguity is not obvious so better to cite more locants. New IUPAC Organic Nomenclature More enclosing marks are used to avoid ambiguity. In most cases fragments with internal locants are enclosed. New IUPAC Organic Nomenclature Enclosing and locants for ring assemblies. Assemblies with suffixes are now enclosed. New IUPAC Organic Nomenclature New numbering for assemblies with three and more members. Assemblies with three to six members are numbered as phanes. Time to Start Programming ACD/Name is the most mature naming program on the market. The development was started in 1994 shortly after ACD/Labs was founded. We support not only organic nomenclature but some inorganic and biochemical nomenclature as well. It is very important that the PIN concept does not make all other names unacceptable. Chemists still have a choice on how to name the compound providing that the chemical name
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