Preliminaries Login to PC Domain: nusstu or nusstf Userid & PW: Use NUSNET ID and PW Download slides at http://bit.ly/reaxys-RUS2017 http://bit.ly/scifinder-RUS2017 Use CHROME Open up 2 websites Library Portal: http://www.lib.nus.edu.sg Google Scholar: http://scholar.google.com

Chemistry Databases Workshop By Dr. Magdeline Ng Ms. Pamela Oon

Research Cycle IDEATION LOTS of information Get your literature review done Do a literature search LOTS of information Organise and manage WIDEN REACH WRITE, PUBLISH and PROTECT your idea

http://libn.us/researcherunbound

Science Resource Team Contact us 6516-2454 sclib@nus.edu.sg

Chemistry Databases: Reaxys & SciFinder Dr Magdeline Ng, NUS Libraries Ms Pamela Oon Researcher Unbound Series – 4 Apr 2017 http://bit.ly/reaxys_RUS2017 http://bit.ly/scifinder_RUS2017

Outline Reaxys & SciFinder Searching SUBSTANCES Searching REACTIONS Searching LITERATURE

Dr Magdeline Ng, NUS Libraries Researcher Unbound Series – 4 Apr 2017 Reaxys Dr Magdeline Ng, NUS Libraries Researcher Unbound Series – 4 Apr 2017 http://bit.ly/reaxys-RUS2017

Steps to access Reaxys Go to Library Portal http://lib.nus.edu.sg Click “Database” tab Select Browse by Database Select “Reaxys” Click “Campus Login” Click “Accept” To create an individual customized ID in Reaxys -> click “Register” **Register using your NUS email address

NUS Library Portal http://libportal.nus.edu.sg/frontend/index

Registration ** Register using your NUS email address

Importance of Chemistry Research in the world Chemistry: 30% of academic output

A research solution built on relevance and discoverabilty >52 M Document records from 16,000 journals and patents describing applications in material sciences, biomedicine, technology, geosciences, engineering, environmental sciences, pharmacology... >90 M Substance records with >500 M excerpted facts on their properties: physical, chemical, spectral, ecological, bioactivity >41 M Reaction records including excerpted data on reaction conditions, solvents, catalyst, yield Linked to Are numbers correct for the new Reaxys 2016? Uses across disciplines Chemistry fundamentals

Evolution of Reaxys (Beilstein and Gmelin database) The Gmelin database is a large database of organometallic and inorganic compounds updated quarterly. It is based on the German publication Gmelins Handbuch der anorganischen Chemie ("Gmelin's handbook of inorganic chemistry") which was originally published by Leopold Gmelin in 1817;[1] the last print edition, the 8th, appeared in the 1990s. The Beilstein database is the largest database in the field of organic chemistry, in which compounds are uniquely identified by their Beilstein Registry Number. The database covers the scientific literature from 1771 to the present and contains experimentally validated information on millions of chemical reactions and substances from original scientific publications. The electronic database was originally created from Beilstein's Handbook of Organic Chemistry, founded by Friedrich Konrad Beilstein in 1881 The database currently contains every compound/reaction discovered between 1772 and 1995,

BASIC SUBSTANCE SEARCHING The main functions needed to search for substances are: Ask Reaxys The Structure Editor Draw the chemical structure The Querylets Chemical Name Molecular Formula

Searching substances by Name Ask Reaxys can be a very good way to find substances where the name is not too complex e.g. 1-fluoronaphthalene

Searching substances by Name Chemical Name Querylet may be searched in two ways: Start typing in the input field Click on “lookup”, start typing and click on the name of the substance you want to search An advantage of using the Chemical Name Querylet is that you see names in the database as you type Finding substances with more complex names can be quite challenging, but seeing options as you type helps significantly e.g. 1-fluoronaphthalene

Searching substances by Formula Ask Reaxys and the Molecular Formula Querylet may be used to find substances by formula. e.g. C10H7F

Searching substances by Name & Formula In cases where there are many substances with the same molecular formula, you may consider combining molecular formula search with a chemical name segment search. E.g. if you wish to find a specific naphthalene which has a methyl (CH3) and a propenyl (CH2- CH=CH2)attachment, you would determine that the molecular formula of the substance is C14H14 Search Substances

Searching substances by Structure Draw the structure Choose Java Free ChemAxon Marvin JS As drawn, where answers have no additional non-hydrogen atoms Retrieve all substances with exactly 1-fluoronaphthalene structure (including substances with C and H isotopes, and substances where 1- fluoronaphthalene is one structure in a multi-component structure)

Searching substances by Structure Create Structure template from name E.g. Fluoronaphthalene and 2- Fluoronaphthalene In some cases, Reaxys will present a number of options, scroll down the list until you find the one that best matches your requirements E.g. himbacine

BASIC REACTION SEARCHING The main functions needed to search for reactions are: Ask Reaxys The Structure Editor Draw the chemical reaction The Querylet Reaction Basic Index

Searching reactions by preparation or synthesis When Ask Reaxys identifies a reaction query, it provides reaction answers directly as shown in the two examples on the right Examples: - preparation of lenalidomide - synthesis of ritalin

Reaction Structure Query Click on Reactions Icon At the bottom of the Structure Editor screen, select the role of the substance(s) drawn How to search reactions by structure: e.g. simple conversion of cyclohexanones to alkoxycarbonylcyclohexanones

Draw the structure query When this query is searched you would get answers where the cyclohexanone part structure appeared in the reactant and the alkoxycarbonylcyclohexanone part structure appeared in the product Many answers would not involve specific conversion of interest Hence it is necessary to tell Reaxys that you want a specific bond to be formed Right click on the bond and click Reacting Centre and change default to Make or Break Transfer query and do a full substructure search (on all atoms)

>1000 reactions are retrieved, and two starting materials are shown on the left. The conversion (reported in different original documents) are shown for Rxn 1, with additional 10 documents reported for this specific conversion Icons such as commercial sources, methods to synthesize the substance Experimental procedure (Find similar reactions)

Reaction Basic Index form searches for text information in the reaction fields To enter more than one term in the Reaction Basic Index consider truncation (which overrides the exact phrase through ‘is’) E.g. stereoselective aldol reactions, consider search terms *stereoselectiv* aldol* Reaxys will AND these terms together and will not search for exact phrase Stereoselectivity of the reaction between cyclohexanone and o- nitrobenzaldehyde Reaction Basic Index

POST-PROCESSING

BASIC LITERATURE SEARCHING The main functions needed to search for reactions are: Ask Reaxys Related to substance Related to literature Related to reactions Reaxys Tree Literature Default Forms

A Question relating to Literature An intelligent ‘Google-like’ experience Ask Reaxys Interprets a natural language question Determines whether the question may primarily relate to substances, reactions or literature Gives answers based on substances, reactions or literature Reaxys search in titles, abstract, and in several different Keyword Fields By default, Reaxys sorts answers based on relevance e.g. effect of global warming on Germany

A Question relating to Substances Many substances records may be found directly through Ask Reaxys Depends on whether you know the simple name for the substance and whether it matched the name of the substance in the database In each example shown, other related substances are found but the substance of interest appears at the top of the list e.g. Cis-platin Morphine

A Question relating to Reactions

ReaxysTree ReaxysTree contains a hierarchy (tree) of index terms At present there are 4 primary trees Each of these may be expanded to narrower levels Ways to use ReaxysTree Expand through tree of interest Search in Find any term box e.g. photochemical cyclizations

Search Forms Default forms in Literature are shown on the right You can set up your own customized literature search form In the input field, you may use: Truncation (* ?) Proximity (NEAR, NEXT) Boolean (AND, OR NOT) Consider using is = exact term (plus additional terms if truncation is used) If you use: starts with, ends with, or contains, you do not need to put in truncation since Reaxys does that automatically for you Search Forms

Searching for authors e.g. DEREK HAROLD RICHARD BARTON Click “lookup” in the Authors querylet then start typing BARTON, D and the drop-down text appears Click barton, d h r and click transfer Continue to type BARTON, DER and more relevant terms appear Click terms and transfer Reaxys has added all the phrases chosen, so click search literature and records for original documents from Professor Sir Derek Barton, Nobel Laureate appears

Searching for journal titles e.g. Angewandte Chemie Angewandte Chemie has been listed in many ways over the years (English and German editions) Choose ‘lookup’ in the Journal Title Querylet to see words and phrases

New Reaxys coming this June…… Clean and intuitive layout with a simple structure makes it easy to use A single and simple UI that interprets the question and gives the right answer Less complexity resulting in less user trainings A familiar search concept everybody knows from Google Query Builder maintains the traditional search style

Thank You Questions? For enquires on how to search the database or looking for specific properties or topics, Please send email to sclib@nus.edu.sg with subject Reaxys query

5-minute Break!