Searching the Chemical Literature: Reference Books and Online Resources Dr. Sheppard Chemistry 4401L

Why search? Physical properties Physical properties –Melting point, boiling point, flash point, refractive index, density, solubility data, toxicity data Developing a synthesis Developing a synthesis Experimental procedures Experimental procedures Spectroscopy data Spectroscopy data –FTIR, 1 H-NMR, 13 C-NMR, MS, UV-VIS Background for research Background for research

Where search? Reference books Reference books –Merck Index –CRC Handbook of Chemistry and Physics –March’s Advanced Organic Chemistry Articles Articles –Google? Google Scholar? –American Chemical Society Publications

The Merck Index A one-volume encyclopedia of chemicals, drugs and biological compounds A one-volume encyclopedia of chemicals, drugs and biological compounds Contains more than 10,000 monographs Contains more than 10,000 monographs –concise descriptions of a single substance or a small group of closely related compounds First published in 1889 First published in 1889 Now the standard reference for chemists, biochemists, pharmacologists, pharmacists, and related professionals Now the standard reference for chemists, biochemists, pharmacologists, pharmacists, and related professionals

Compounds in the Merck Index Human and veterinary drugs Human and veterinary drugs Biologicals and natural products Biologicals and natural products Plants and herbal medicines Plants and herbal medicines Nutraceuticals and cosmeceuticals Nutraceuticals and cosmeceuticals Agricultural chemicals Agricultural chemicals Industrial chemicals Industrial chemicals Laboratory reagents and catalysts Laboratory reagents and catalysts Dyes, colors and indicators Dyes, colors and indicators Environmentally significant substances Environmentally significant substances

Information in the Merck Index Chemical, common and generic names Chemical, common and generic names Trademarks and associated companies Trademarks and associated companies CAS Registry Number CAS Registry Number Chemical structure Chemical structure Molecular formula and percentage composition Molecular formula and percentage composition Capsule statement identifying compound classes and scientific significance Capsule statement identifying compound classes and scientific significance Scientific and patent literature references Scientific and patent literature references Physical and toxicity data Physical and toxicity data Therapeutic and commercial uses Therapeutic and commercial uses Caution and hazard information Caution and hazard information

Also in the Merck Index Indices Indices –Name, Formula, CAS Registry Number Supplementary tables (some editions) Supplementary tables (some editions) –Physical, chemical and biomedical data –Listings of pharmaceutical company names and locations –Experimental drug codes Organic Name Reactions section (some editions) Organic Name Reactions section (some editions) –Over 450 reactions featuring descriptions, literature references and graphical depictions

Merck Index, 14 th ed. Entry for cholesterol

Merck Index, 14 th ed. Registry Index

Merck Index, 14 th ed. Chemical Formula Index

Merck Index, 14 th ed. Name Index

Merck Index, 14 th ed. Entry for heroin

CRC Handbook of Chemistry and Physics Table of Physical Constants for Organic Compounds Table of Physical Constants for Organic Compounds Listed in alphabetical order by parent name Listed in alphabetical order by parent name –2-phenylethanol is under ethanol, 2-phenyl Abbreviations, subscripts, superscripts Abbreviations, subscripts, superscripts –Example: what does it mean if a boiling point is listed as , ?

CRC Handbook, 42 nd ed. Entry for cholesterol

CRC Handbook,42 nd ed. Abbreviations for table

CRC Handbook, 42 nd ed. Entry for methyl benzoate

CRC Handbook, 1 st student edition Entry for cholesterol

Organic Reactions Organic Synthesis Organic Synthesis Organic Synthesis Organic Synthesis –11 collective volumes –Search using substructure, reaction, keyword, name, CAS number, or volume March’s Advanced Organic Chemistry March’s Advanced Organic Chemistry

March, 4 th ed.

So, where are the reference books? CRC CRC –CSU Library (currently being repaired) –Dr. Sheppard’s office (Student and regular editions) –Chemistry lab (2 editions) Merck Index Merck Index –Dr. Sheppard’s office (1 copy) –CSU Library (1 copy on reserve under General Chemistry) March’s Advanced Organic Chemistry March’s Advanced Organic Chemistry –Dr. Sheppard’s office (2 editions) –CSU Library (2 in circulating collection, 1 in reference collection)

Journal Articles and Databases Primary (original) vs. Secondary (reviews, accounts) Primary (original) vs. Secondary (reviews, accounts) Journal abbreviations (see next slide) Journal abbreviations (see next slide)

Journal Articles and Databases Chemical Abstracts, Beilstein Chemical Abstracts, Beilstein SciFinder SciFinder Google Scholar Google Scholar Google Scholar Google Scholar ACS Publications ACS Publications ACS Publications ACS Publications –Available on-campus only – –Content = 1996 to present   Pre-1996 available through interlibrary loan –Chemical and Engineering News Chemical and Engineering NewsChemical and Engineering News GALILEO GALILEO GALILEO JStor (Science) JStor (Science) JStor

Websites When to use the web instead of reference books or journal databases? When to use the web instead of reference books or journal databases? Is Wikipedia a good resource? Is Wikipedia a good resource? Use websites with caution! Use websites with caution! Always provide citation with web address and date website was accessed Always provide citation with web address and date website was accessed Don’t forget about textbooks as good resources Don’t forget about textbooks as good resources

Spectroscopy websites National Institute of Standards and Technology Chemistry WebBook National Institute of Standards and Technology Chemistry WebBook National Institute of Standards and Technology Chemistry WebBook National Institute of Standards and Technology Chemistry WebBook –Mass Spectrometry and Infrared Spectroscopy data, thermochemical data, and much, much more. Spectral Data Base System for Organic Compounds (SDBS) Spectral Data Base System for Organic Compounds (SDBS) Spectral Data Base System for Organic Compounds (SDBS) Spectral Data Base System for Organic Compounds (SDBS) –Huge searchable database of spectra, including IR, NMR, and MS.

Safety Information Vermont SIRI MSDS Collection Vermont SIRI MSDS Collection Vermont SIRI MSDS Collection Vermont SIRI MSDS Collection –Provides access to Material Safety Data Sheets directly from chemical manufacturers and from an online database. Chemical Toxicity reports can also be found at this site.

Physical Constants Fundamental Physical Constants from NIST Fundamental Physical Constants from NIST Fundamental Physical Constants from NIST Fundamental Physical Constants from NIST –Provided by the Fundamental Constants Data Center of the National Institute of Standards and Technology Physics Laboratory

ChemDraw Std 14.0 Download the program Download the program – – e.cfm?sid=2560http://sitelicense.cambridgesoft.com/sitelicens e.cfm?sid=2560 –Use Internet Explorer or Firefox –Use your CSU to log on and follow instructions to download the program –Earlier versions of the program are acceptable Program tutorial Program tutorial