Organic Chemistry

Reference Guide: Organic Chemistry Selected Starting Points, Davidson Library, UCSB

Other Chemistry Reference Guides: Analytical Chemistry Biochemistry General Chemistry Inorganic Chemistry Organic Chemistry Physical Chemistry

General Overview Works | Organic Synthesis References |
Physical Properties and Characterization | Locating Articles | Internet Resources

Locating Books

To locate books on your topic, use the PEGASUS Online Catalog (http://pegasus.library.ucsb.edu/F/). As a starting point, use a keyword search on the likely terms. You are unlikely to find references to a single compound, but may be able to find useful books on classes of compounds, such as esters, carboxylic acids, or polymers. For the most general case, use organic compounds. For synthesis information, combine the compound class term with synthesis. For properties, use the specific property name (e.g. solubility, spectra, toxicology.) For collections of data, use handbooks or tables. Examples: amines synthesis, organophosphorus toxicology, organic compounds handbooks

If nothing comes up, try a broader class term, or try your class term without a qualifier. When you find a relevant record, check its subject headings to see if there is alternative terminology you should try. Similarly, use keyword searches to find books on particular methods or reactions (e.g., addition reactions, ring formation). You may also want to browse in the book stacks.

• Organic analysis: QD 271-272
• Organic synthetic methods: QD 262 and QD 281.
• Specific classes of compounds:QD 300-406
• Organometallics: QD 410-412
• Physical organic chemistry: QD 476

General Overview Works

CHEMLIBnetBASE (http://www.chemlibnetbase.com)
CHEMLIBnetBASE is a collection of texts from Taylor & Francis/CRC Press in full-text electronic form, including over 40 titles in organic and natural products chemistry.

"Comprehensive Chemistry" series
Comprehensive Heterocyclic Chemistry    Ref QD 400 .C65 1984
Comprehensive Heterocyclic Chemistry II    Ref QD 400 .C65 1996
Comprehensive Natural Products Chemistry    Ref QD 415 .C63 1999
Comprehensive Organic Chemistry    Ref QD 245 .C65
Comprehensive Organic Functional Group Transformations    Ref QD 262 .C534 1995
Comprehensive Organic Functional Group Transformations II    Ref QD 262 .C534 2005
Comprehensive Organic Synthesis    Ref QD 262 .C535 1991
Comprehensive Organometallic Chemistry    Ref QD 411 .C65 1982
Comprehensive Organometallic Chemistry II    Ref QD 411 .C652 1995
Comprehensive Organometallic Chemistry III    (SEL Ref QD411 .C653 2007)
Comprehensive Polymer Science    Ref QD 381 .C66 1989
Comprehensive Supramolecular Chemistry    Ref QD 411 .C66 1996
       (for cryptands and other host-guest molecules)

These sets from Pergamon Press contain excellent review articles on various aspects of their respective subjects, and make good starting points for new research. The oldest of these, Comprehensive Organic Chemistry, is becoming somewhat dated, but is still useful. Each set is organized into volumes on broad subject areas; it's best to consult the subject indexes to locate your topic. Most of the sets also have an excellent molecular formula index.

"Dictionary of Compounds" Series
These series are alphabetical lists of compounds, with excellent indexing (including synonyms, molecular formula, and CAS Registry Numbers). Each compound entry provides basic physical data, with references to other data, including methods of preparation. Note that for any given compound, much of the data is duplicated from one set to the other.

Dictionary of Analytical Reagents    Ref QD 77 .D498 1993
Dictionary of Antibiotics    Ref RS 431 .A6 D53 1988
Dictionary of Drugs    Ref RS 51 .D479 1990
Dictionary of Organic Compounds, 6th ed.    Ref QD 251 .D5 1996
Dictionary of Natural Products    Ref QD 415 .A25 D53 1994
Dictionary of Organometallic Compounds, 2nd ed.    Ref QD 411 .D53 1995
Dictionary of Organophosphorus Compounds    Ref QD 412 .P1 E36 1988
Dictionary of Steroids    Ref QP 752 .S7 D53 1991
Dictionary of Terpenoids    Ref QD 416 .C75 1991

All of the above "Dictionaries" are available online in "Combined Chemical Dictionary", a part of CHEMnetBASE (http://www.chemnetbase.com. In CHEMnetBASE, the dictionaries are searchable by chemical name, formula, physical properties and, with the proper browser plug-in, by structure or substructute.

Organic Chemist's Desk Reference    Ref QD 246 .D5 1996 suppl. gives a user's guide to DOC, with abbreviations, definitions and some useful property tables.

Studies in Natural Products Chemistry    QD 415 .A2 S78 1988
An ongoing series of volumes of review articles, mainly dealing with synthesis, but also delving into the biological activity of a wide variety of natural products. UCSB currently owns volumes 1-18.

Chemistry of Heterocyclic Compounds    QD 400 .C5
This ongoing multi-volume series (over 56 volumes, some in multiple parts) covers heterocyclic chemistry in depth. Each volume is devoted to a different class of compound (by size and number of rings and number and type of heteroatoms.)

Porphyrin Handbook    Ref QP 671 .P6 P67 2000
Very up-to-date and comprehensive ten-volume work on the organic and organometallic chemistry and biochemistry of porphyrins.

CrossFire Beilstein/Gmelin
The Beilstein Handbook is the most comprehensive sourse of evaluated data and references in organic chemistry, running hundreds of volumes in print. We now have access online via CrossFire. CrossFire permits quick and powerful searching by text terms, numeric data, and chemical structures of two of the world's largest databases of chemical information, the Beilstein database and the Gmelin database. The MDL® CrossFire Commander software includes a structure drawing tool for structure and substructure searching of chemicals and reactions, and the AutoNom tool for generating standard chemical names from a drawn structure. The Beilstein database of organic chemistry includes records from the mid-1800's to the present, for more than 8.8 million substances, 9 million reactions, and titles and abstracts for about 2 million documents (since 1980) in organic chemistry.

Note that CrossFire is a client/server product, and the client must be installed on the terminal where you wish to use it. It can be downloaded and installed on any UCSB campus terminal, and is available on certain public workstations in the Davidson Library.

Organic Synthesis References

Organic Reactions    Ref QD 251 .O68
Annual publication with review articles on important synthetic methods. Articles are published in no particular order, but the series is well indexed, with cumulative author and chapter/topic indexes in each volume for all the preceding volumes.

Organic Syntheses
Available in print at SEL Refernce Area, Ref QD 262 .O68
Annual publication with tested syntheses of organic and organometallic compounds. Gives detailed descriptions of synthetic techniques, reagents, yields and safety aspects. It is well indexed by authors, compound names, reaction types, and molecular formulas.
The print collective volumes include revised and updated syntheses from annual volumes. There is a cumulative index for the first eight collective volumes.
The online version is freely available to the public and contains the contents of the entire series, up to one year before the present, searchable by chemical name, CAS Registry Number, other text terms, and by structure or substructure. Use of this excellent database requires a Java-capable browser.

Comprehensive Organic Transformations, 2nd ed.    Ref QD 262 .L355 1999
This newly-updated guide to functional group preparations by Richard C. Larock, is organized by the type of compound (e.g. alkanes, esters, nitriles), then by the method of preparation (reduction, alkylation), then by the type of starting material. Each section gives references to review articles, as well as a list of specific examples with references. This edition covers the literature up to 1995. The first edition, published in 1989, is available for check out.

Name Reactions and Reagents in Organic Synthesis    Ref QD 291 .N86 1988
Many reactions and reagents in organic synthesis have been named for their discoverers. This volume lists name reactions, with general scheme, mechanism and examples and name reagents, with uses, preparations, precautions and examples. Both sections have cross-references to March's Advanced Organic Chemistry (QD 251.2 .M37, which edition is unspecified) and the reagents section cross-references to Fieser and Fieser (see below.)

Fieser and Fieser's Reagents for Organic Synthesis    Ref QD 262 .F5
Classic series reporting on new reagents and new uses for old reagents. Alphabetical list of reagents, with author and subject index. Cumulative index for Vols. 1-12.

Encyclopedia of Reagents for Organic Synthesis     Ref QD 77 .E53 1995
This popular resource contains articles on the reagent use of hundreds of different chemicals. The articles give physical data and brief, but detailed description of uses. Excellent references and indexing (compound name, formula, type of reaction) Articles are arranged alphabetically by reagent name.

Physical Properties and Characterization

Merck Index (https://themerckindex.cambridgesoft.com/)    SEL Desk RS 356 .M4
Published by Merck Pharmaceuticals, with data primarily on organics, strongest on drugs. It is organized by chemical name, usually the common or trade name. It includes physical data, preparation references, toxicity and uses. Merck is well-indexed, by Registry Number, molecular formula and synonyms. The online version may be searched by text terms or numeric properties, or by structure (with the appropriate browser plug-in.) Both print and online versions include a dictionary of name reactions in organic chemistry, with reaction diagrams.

Aldrich Catalog (http://www.sigmaaldrich.com/>)   SEL Desk TP 202 .A48, also uncataloged copies
In addition to serving as an alphabetical catalog of the chemicals available from Aldrich, it includes basic physical data, cross-references to Beilstein, Merck and Fieser, and safety information. It has indexes by molecular formula and CAS Registry Number. The online version is free, and contains the same data, plus links to Aldrich's FT-IR, Raman and NMR spectra, and Materials Safety Data Sheets.

See also other chemical companies catalogs, both in print (on catalog shelf near SEL Desk) and on the Web. Check InfoSurf Chemistry: Chemical Suppliers at http://www.library.ucsb.edu/subjects/chem/chemist4.html#chemicals.

Handbook of Organic Chemistry    Ref QD 251.2 .D43 1987
Contains a host of tables of organic chemical properties. In some respects it is more complete than the CRC above, and perhaps easier to use.

ChemFinder WebServer http://chemfinder.cambridgesoft.com/
This database, provided by CambridgeSoft, provides basic physical data and structure diagrams. It also has links to websites containing other data for a large number of chemical compounds. It is searchable by name, molecular weight, molecular formula, and CAS Registry Number.

Organic Compounds Database http://www.colby.edu/chemistry/cmp/cmp.html
This database, compiled at Virginia Tech and made available by Colby College, provides physical data on a large number of organic compounds, including molecular weight, melting point, boiling point, index of refraction and UV absorption and mass spectral peaks. It is searchable by name, molecular formula or by data values for the above properties.

CRC Handbook of Data on Organic Compounds (HODOC)    Ref QD 257.7 .H36
This multi-volume set gives structures, basic physical properties of organic compounds and references to find compounds in Beilstein and to Sadtler spectra collections. Compounds are listed in alphabetical order by their CAS systematic names. It has indexes for synonyms, formulas, spectral peaks, and CAS Registry Numbers. Now in its 3rd edition.

Handbook of Physical Properties of Organic Compounds    Ref QD 257.7 .H374 1997
This single volume work gives structure and data important to environmental fate of compounds (mp, bp, water solubility, octanol-water partition coefficient, vapor pressure, pKa, Henry's Law constant, and atmospheric hydroxyl radical reaction rate constant), and references. It is arranged by CAS Registry Number, with name and molecular formula indexes. Available online as part of CHEMnetBASE, see above.

Spectra: For Spectra sources, see the appropriate section of the General Chemistry guide.
For sample problems in organic compound characterization, try these sites:
WebSpectra (http://w3.chem.ucla.edu/~webspectra/)
This UCLA website has 75 compounds of varying levels of difficulty.

Organic Structure Elucidation (http://www.nd.edu/~smithgrp/structure/workbook.html)
This site from Notre Dame has 64 problems of varying levels of difficulty.

Locating Articles

Web of Science (Science Citation Index): The Science Citation Index database in Web of Science covers some 3600 journals in the sciences. It covers 1945-present, and for recent years has searchable abstracts. It also has searchable cited references, so you can track an older reference on, for instance, a synthetic method forward to more recent applications or to other related records. It is only available on campus, from ucsb.edu addresses.

Methods in Organic Synthesis: MOS provides quick, cost-effective access to important new developments in organic synthesis. It covers such topics as new reactions and reagents, functional group changes, the introduction of chiral centers, and enzyme and biological transformations. Items are selected for inclusion in MOS only where there is detail of novel or interesting features in organic synthetic methods so that there are no routine preparations to plow through. Each MOS item includes reaction schemes, title and bibliographic details, and the items are categorised by five indexes: Author, Product, Reaction, Reactant and Reagent. MOS covers late 1999 to the present. It is only available from ucsb.edu addresses.

Natural Product Updates: NPU is a unique source of current information in natural product chemistry, providing quick access to recent signficant advances in the subject. NPU covers new natural products, known compounds from new sources, isolation studies, structural determinations, new properties and activities, biosynthesis and biological activities. Each monthly issue contains approximately 200 items with structure diagrams, together with trivial and taxonomic names, molecular formulae, physical properties, and spectral data. NPU has six indexes: Authors, Non-plant sources, Taxonomic names, Biological activity, Compound Class and Trivial names. NPU covers late 1999 to the present. It is only available from ucsb.edu addresses.

SciFinder Scholar: SFS is an end-user oriented interface to the Chemical Abstracts Service databases: CAPLUS, REGISTRY, CASREACT,and CHEMCATS. Its databases cover the entire literature of chemistry, including journal articles, patents, conference papers and more, from before 1900 to the present, by far the most comprehensive database of the chemical literature. It may be searched by author, topic, corporate source, chemical name, molecular formula or chemical structure (including substructures and reaction diagrams).

It is available in two versions:SciFinder Web uses a Web browser interface. Users must first register, using a valid ucsb.edu e-mail address. It is compatible with the campus proxy server for off campus use. SciFinder Scholar is a client-server system, which requires installation of the SFS client on the terminal where you wish to use it. The client may be downloaded and installed on any Windows or Mac computer by a UCSB user. In the UCSB Davidson Library, SciFinder is available at selected workstations in the Sciences-Engineering Library (2nd floor North).

Other Internet Resources

More and more resources of value to the organic chemist are becoming available over the World Wide Web. Some are available free of charge, some are not. You may try using Internet search engines such as Yahoo, Infoseek, Alta Vista, etc.; however, depending on the keywords you choose, you may find nothing, or you may find large amounts of irrelevant material. It can be more effective to seek out sites which are specifically devoted to chemical information. Many such links can be found on the UCSB Library's InfoSurf Chemistry page (http://www.library.ucsb.edu/subjects/chem/chemistr.html). Besides those mentioned in other sections above, some particular sites of interest to organic chemists include:

• IUPAC Chemical Nomenclature http://www.chem.qmw.ac.uk/iupac/
  This site, created by G.P. Moss of Queen Mary and Westfield College, contains a number of IUPAC documents on organic and biochemical nomenclature, in many cases including sample structure diagrams.

• IUPAC Nomenclature of Organic Chemistry http://www.acdlabs.com/iupac/nomenclature/
  Another good nomenclature site, easily browsable and searchable, provided by Advanced Chemistry Development (ACD) Inc.