E-EROS TUTORIAL Encyclopedia of Reagents for Organic Synthesis

at the UIUC Chemistry Library For any questions about e-EROS please contact Tina Chrzastowski or call (217) 333-3737.

Introduction About e-EROS: Encyclopedia of Reagents for Organic Synthesis e-EROS is the electronic counterpart of the print version of the Encyclopedia. The database contains around 50,000 reactions and 3,800 of the most frequently consulted reagents. To open e-EROS, go to the Chemistry Library's homepage (http://www.library.uiuc.edu/chx/) and look for the e-EROS link under "Electronic Reference."

Starting to Use e-EROS When you first open e-EROS from the Chemistry Library's homepage, you will see what information e-EROS has to offer.

The database is searchable through browsing the index, keyword searching or through Structure & Metadata searching. The Structure & Metadata search first consists of drawing structures (for the substructure, structure exact or reaction substructure). To narrow the results, the database can then be searched by: reagent name, reaction name, catalyst name, solvent name, product yield, temperature, authors, reference and publication year. Each entry highlights the various uses and characteristics of each reagent through: illustrations, information on physical data, solubility, the form it is supplied in, purification, and where relevant, preparative methods. Each entry has a list of literature references to key review articles and seminal papers.

For the purpose of this tutorial we will search for information on Iodine.

Basic Searches Searching by browsing the index of reagents Click on the link "Browse articles by Reagent Name" on the main e-EROS website.

The reagents are listed by abbreviations, alphabetically and by the date that they became available to the database. To find information on Iodine, open the folder labeled "Dip-K" and then scroll down to the Iodine entry.

There are a number of Iodine entries, including: Iodine Iodine Azide Iodine Nitrate Iodine-Silver(I) Fluoride Etc.

By clicking on the link to Iodine Nitrate you will get information on: its properties, see examples of its structure through illustrations and have access to different references. Note that the same information can be found in the print version. Searching by keyword Keyword searching can be used more effectively if you use combined search terms or use Boolean searching. Boolean searching has to do with phrasing words together using AND, OR, or NOT when

searching. In example, typing in "Iodine" AND "2004" suggest that entries that have both the words Iodine AND the number 2004 will come up. If you type in "Iodine" OR "Nitrate", then the entries that either have Iodine OR Nitrate, or have both Iodine and Nitrate in the entry, will come up in the search. If you type in "Iodine" NOT "Nitrate", then all articles that contain Iodine but NOT Nitrate will appear. There are two other ways to enhance your search. First, to narrow your search, e-EROS does allow for quotation marks. If there is a phrase you wish to search for, using quotation marks will limit your search to only entries that have those words next to each other. Second, using truncations can expand your search. Truncations are symbols such as * or ? and indicate you want any word that stems from the original word. If you type the search term "Iodine*", the database knows that you want information on Iodine or any form of Iodine, such as Iodine-copper. To use a keyword search, start from the e-EROS home page and type into the search box:

By only typing in Iodine and then hitting the search button there are 569 hits. By clicking on the link called "edit results", you can narrow the results by using Boolean search terms or using the supplied categories. In this example, Iodine is limited to what is found in: Fulltext/Abstracts, in journals, and had to be published between the dates of Nov. 2004-Dec. 2004.

This results in 9 hits.

Note: You could also go to the Advanced Search link from the e-EROS homepage for this option.

Structure & Metadata Search: Drawing Structures and Reactions How to use the drawing tools From the homepage of e-EROS, click on the "search in this title" link.

From here you will see the option of either plugging in keywords for a text only search or to use the Structure and Metadata Search format. Note that to use this searching format, you must search by one of the three following terms for the first box: by Substructure, by Structure (exact) or by Reaction (Substructure). For this example, we will search for a reaction for when Iodine is added to cyclohexene.

A second window pops-up in order to draw the structure or reaction. There are a number of tools to use in drawing the structure or reaction.

The most common element letters are found on the left hand side of the window: C, N, O, S, F, Cl, Br, P, A, and Q. The letter X brings up the Periodic Table to select a different atom. The letter L is the "Select Atomlist" table. In this table you can modify the elements by changing the Hydrogen Count, or clicking on "not-list" you can choose elements that you do not want associated with the specific structure being drawn. (in example, different variations of Iodine have the similar structures. To make sure certain Iodine compounds do not appear, use the "not-list" option.)

OPENS TO

OPENS TO

The different drawing tools are available to create the structure. (Note: When creating a reaction (substructure), remember you must include AT LEAST one reactant, one reaction arrow and one product, in the drawing.)

Once the structure is completed, click on the transfer button to bring the image into your search.

Structure & Metadata Search: Combining Search Terms When the structure is drawn, then you can do a search. In this first example, the reaction of adding Iodine to cyclohexene is found in only one article.

To look at the structure or reaction more closely, click on the magnifying glass icon. To see the article that has this structure, click on the link. You will see that this reaction drawing leads us back to the original Iodine article.

Advanced searching with structures If the search is for a more common structure in which there are a lot of articles, there are a number of ways to narrow the search down. In example, if the goal was to see what articles contained a reaction with Iodine, you would create a substructure.

Once the structure is drawn and transferred to the search screen, the searching can be narrowed by a number of terms.

The search terms are: reagent name, reaction name, catalyst name, solvent name, product yield, temperature, authors, reference and publication year. With this example we will search for the reagent name of Iodine to go along with the Iodine substructure drawing.

The result is the 25 articles.

Conclusion There are many ways to search through e-EROS depending upon what type of information there is available. If there is only a structure available, then doing a Structure & Metadata search would be the most productive. If there is only a structure name available, and there is a need for general information on it, then using the Browse search would be the most effective. If there is a specific topic in mind involving a known structure, then a keyword search might be the most productive.